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α-水芹烯 | 99-83-2

中文名称
α-水芹烯
中文别名
Alpha-水芹烯,天然品;水芹烯
英文名称
p-mentha-1,5-diene
英文别名
α-phellandrene;alpha-phellandrene;phellandrene;2-methyl-5-propan-2-ylcyclohexa-1,3-diene
α-水芹烯化学式
CAS
99-83-2
化学式
C10H16
mdl
MFCD00062988
分子量
136.237
InChiKey
OGLDWXZKYODSOB-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    185.55°C (rough estimate)
  • 密度:
    0.85 g/mL at 25 °C(lit.)
  • 闪点:
    117 °F
  • 溶解度:
    苯:可溶;氯仿:可溶
  • 熔点:
    <25 °C
  • LogP:
    4.43
  • 物理描述:
    Liquid
  • 颜色/状态:
    COLORLESS OIL
  • 蒸汽压力:
    1.40 mmHg
  • 大气OH速率常数:
    3.13e-10 cm3/molecule*sec
  • 折光率:
    1.471-1.477
  • 保留指数:
    997;1007;998;996;996;998;1000;1028;994;998;999;1004;997;1022;1008;998;1003;1041;998;998;1003;1002;992;989;998;991;995;1001;996;1001;997;998;997;997;1005;994;997;997;989;990;991;974;991.1;998;997;989;993;993;997;1003;997;997;993;993;998;997;998;997;999;1005;1003.2;997;1002;993;1007;995;1002;999;1004;1000;994;1009;1002;1002;996;1001;995;994;1000;1003.67;1006.67;1009.74;1012.78;1015.83;1019.04;986.95;989.59;992.3;995.05;997.86;1008;999;1009;1002;1002;999;997;1009;992;994;1001;999;999;998;1003;995;1003;995;994;995;994;1017;995;996;997;998;1000;1000;1002;994;997;998;1000;1001;1001.4;998;1002;998;998;1003;1009;1000;1002;1013;1027;985;1003.7;1007.1;1012;1000;995;999;1002;1002;997;997;1002;985;1005;1005;999;1002;991;1002;997;993;996;1000;1008;1003;1013;995;995;1002;998;995;984;1012;995;997;995;1003;1005;998;1005;1003;999;1002;997;997;997;996;1003;997;1004;998;1002;999;1006;999;1003;1016;989;995;992;986;995;1003;1005;1003;1005;995;996;995;1005;1004;1002;1002;1004;1005;1027;995;1003;1003;990;1001;989;987;999;1003;997;1004;1005;990;1001;1001;1004;995;1002;999;1003;994;995;1001;1006;1006;998;998;1002;1006;994;999;995;995;1015;1006;996;1003;1012;1000;1007.2;989;999;1000;998;1027;997;984;1007;1008;1000;1002;1004;1010;993;992;999;989;987;1000;988;993;995;998;991;1009;998;998;1002;1002;1002;1002;988;995;1007;1005;997;994;996;1002;993;997;1000;1002;999;1004;993;992;1001;995;996;1005.2;995;997;999;998;995;998;993;1001;993;995;1013;1013;1000;1000;994;995;995;1000;997;997;992;994;996;995;994;994;993;1000;997;1002;990;999;1000;996;996;988;1003;1005;998;993;993;1003;1004;1005;996;1000;993;1002;994;994;992;993;993;1000

计算性质

  • 辛醇/水分配系数(LogP):
    3.2
  • 重原子数:
    10
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.6
  • 拓扑面积:
    0
  • 氢给体数:
    0
  • 氢受体数:
    0

ADMET

代谢
...ALPHA-PHELLANDRENE...被代谢成P-MENTHANE衍生物,PHELLANDRIC ACID,通过减少环己二烯环中1个双键的还原反应...
...ALPHA-PHELLANDRENE...IS METABOLIZED INTO P-MENTHANE DERIV, PHELLANDRIC ACID, BY REDN OF 1 OF THE DOUBLE BONDS OF THE CYCLOHEXADIENE RING...
来源:Hazardous Substances Data Bank (HSDB)
代谢
在绵羊中,α-防风素显然经历了一个双键的还原和一个甲基基团的氧化,生成防风醇,进一步氧化为防风酸,通过尿液排出。建议它被2,3,5-三羟基化为对-薄荷醇,并作为葡萄糖苷酸排出。
IN SHEEP, ALPHA-PHELLANTHRENE APPARENTLY UNDERGOES REDN OF ONE DOUBLE BOND & OXIDN OF METHYL GROUP TO GIVE PHELLANDRAL, FURTHER OXIDIZED TO PHELLANDRIC ACID, EXCRETED IN URINE. SUGGESTED THAT IT IS 2,3,5-TRIHYDROXYLATED TO P-MENTHOTRIOL & EXCRETED AS GLUCURONIDE.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
...可能对皮肤产生刺激,并能通过皮肤被吸收。摄入可能导致呕吐和腹泻。
...CAN BE IRRITATING TO, & ABSORBED THROUGH, SKIN. INGESTION CAN CAUSE VOMITING, DIARRHEA.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
由于牙齿制剂中的3种成分:α-蒎烯、柠檬烯和松油醇具有致敏性质,发现了超敏反应。
HYPERSENSITIVITY FOUND DUE TO SENSITIZING PROPERTIES OF 3 INGREDIENTS: ALPHA-PINENE, LIMONENE, & PHELLANDRENE IN DENTAL PREPN.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 非人类毒性摘录
将ALPHA-PHELLANDRENE以最大浓度应用于完整或磨损的兔皮,在封闭条件下持续24小时,具有中等刺激性。
ALPHA-PHELLANDRENE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS MODERATELY IRRITATING.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
经皮肤吸收。
...ABSORBED THROUGH, SKIN.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    3.2
  • 危险品标志:
    Xn,F
  • 安全说明:
    S16,S26,S36/37
  • 危险类别码:
    R22,R10,R36/37/38,R43
  • WGK Germany:
    2,3
  • 海关编码:
    2902199090
  • 危险品运输编号:
    UN 2319 3
  • 危险类别:
    3.2
  • 包装等级:
    III
  • 危险性防范说明:
    P210,P233,P240,P241,P242,P243,P261,P264,P270,P271,P280,P285,P301+P312,P303+P361+P353,P304+P340,P305+P351+P338,P321,P330,P332+P313,P337+P313,P342+P311,P362,P370+P378,P403+P233,P403+P235,P405,P501
  • 危险性描述:
    H226,H302,H315,H319,H334,H335
  • 储存条件:
    室温

SDS

SDS:664d91205df1babf44f640a94bb58f2c
查看

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : α-Phellandrene
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 99-83-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances



SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Flammable liquids (Category 3), H226
Acute toxicity, Oral (Category 4), H302
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Respiratory sensitisation (Category 1), H334
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn, F Harmful, Flammable R10, R22, R36/37/38, R43
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing vapours.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P342 + P311 If experiencing respiratory symptoms: Call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards
Rapidly absorbed through skin.

SECTION 3: Composition/information on ingredients
Substances
Formula : C10H16
Molecular Weight : 136,23 g/mol
CAS-No. : 99-83-2
EC-No. : 202-792-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
p-Mentha-1,5-diene
CAS-No. 99-83-2 Flam. Liq. 3; Acute Tox. 4; 50 - 100 %
EC-No. 202-792-5 Skin Irrit. 2; Eye Irrit. 2; Resp.
Sens. 1; STOT SE 3; H226,
H302, H315, H319, H334,
H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
p-Mentha-1,5-diene
CAS-No. 99-83-2 Xn, F, R10 - R22 - R36/37/38 - 50 - 100 %
EC-No. 202-792-5 R43
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to
form explosive concentrations. Vapours can accumulate in low areas.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Air and light sensitive.
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 171,5 °C at 1.013 hPa
boiling range
g) Flash point 47 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 0,85 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,36 - The preceding data, or interpretation of data, was
octanol/water determined using Quantitative Structure Activity Relationship (QSAR)
modeling.
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
Heat, flames and sparks.
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Inhalation: no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: OS8080000
burning sensation, Cough, wheezing, laryngitis, Shortness of breath, Headache, Nausea, Vomiting, To the
best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.

SECTION 12: Ecological information
Toxicity
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company.
Contaminated packaging
Dispose of as unused product.

SECTION 14: Transport information
UN number
ADR/RID: 2319 IMDG: 2319 IATA: 2319
UN proper shipping name
ADR/RID: TERPENE HYDROCARBONS, N.O.S.
IMDG: TERPENE HYDROCARBONS, N.O.S.
IATA: Terpene hydrocarbons, n.o.s.
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
Flam. Liq. Flammable liquids
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H335 May cause respiratory irritation.
Resp. Sens. Respiratory sensitisation
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
F Flammable
Xn Harmful
R10 Flammable.
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
R43 May cause sensitisation by skin contact.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

毒性

GRAS(FEMA)。

LD₅₀值为5700 mg/kg(大鼠,经口)。

使用限量

FEMA (mg/kg):
软饮料 10;
冷饮 28;
糖果 130;
焙烤食品 41。
适度为限(FDA §172.515,2000)。

食品添加剂最大允许使用量与最大允许残留量标准
  • 添加剂中文名称:α-水芹烯
  • 允许使用该种添加剂的食品中文名称:食品
  • 添加剂功能:食品用香料
  • 最大允许使用量(g/kg):用于配制香精的各香料成分不得超过在GB 2760中的最大允许使用量和最大允许残留量
化学性质

α-水芹烯是一种无色至微黄色油状液体,具有黑胡椒和柑橘似香气。它存在两种异构物:右旋体沸点为66~68℃(2133Pa),左旋体沸点为58~59℃。闪点约为49℃。该物质溶于乙醇和乙醚,而不溶于水。

右旋体存在于肉桂油、姜油、榄香脂油、小茴香油等中;而左旋体则存在于桉叶油、八角茴香油、甘榻油、月桂油、胡椒油等中。

用途

GB 2760—1996 规定α-水芹烯为允许使用的食用香料。主要用于配制柑橘类和香辛料类人造精油。

生产方法

通过真空分馏法从含量较高的精油中单离得到。

反应信息

  • 作为反应物:
    描述:
    α-水芹烯 在 ruthenium(III) trichloride hydrate 作用下, 以 乙醇 为溶剂, 反应 4.0h, 以11%的产率得到[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
    参考文献:
    名称:
    [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION
    [FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT D'UNE INFLAMMATION
    摘要:
    这项发明涉及新型利用新型resolvin化合物和其药物制剂的治疗方法。
    公开号:
    WO2010120719A1
  • 作为产物:
    描述:
    胡椒酮乙醇sodium 作用下, 生成 α-水芹烯
    参考文献:
    名称:
    Read; Cook, Journal of the Chemical Society, 1925, vol. 127, p. 2787
    摘要:
    DOI:
  • 作为试剂:
    描述:
    1-溴-2-萘酚吡啶盐酸copper(l) iodide正丁基锂α-水芹烯乙基溴化镁四丁基氟化铵氯化铂 、 cesium fluoride 作用下, 以 四氢呋喃乙醚正己烷二氯甲烷1,2-二氯乙烷异丙醇甲苯 为溶剂, 反应 41.0h, 生成 (P)-1-aza[6]helicene
    参考文献:
    名称:
    A Scalable and Expedient Route to 1-Aza[6]helicene Derivatives and Its Subsequent Application to a Chiral-Relay Asymmetric Strategy
    摘要:
    A rapid route to diversely functionalized 1-aza[6]helicenes has been achieved via the development of a copper-mediated cross-coupling reaction, followed by PtCl4-catalyzed cycloisomerization. Not only does this method allow access to these functionally important molecules on gram scale, but this strategy Is also suitable for relaying the axial chirality of a key intermediate to the helicity of the product.
    DOI:
    10.1021/ol400493x
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文献信息

  • Enantioselective transfer hydrogenation of pro-chiral ketones catalyzed by novel ruthenium and iridium complexes of well-designed phosphinite ligand
    作者:Nevin Arslan
    DOI:10.1080/10426507.2019.1704285
    日期:2020.8.2
    hydrogenation of acetophenone derivatives using 2-propanol as a hydrogen source. The results showed that the corresponding alcohols could be obtained with good activity (up to 55% ee and 99% conversion) under mild conditions. Notably, [Ir((Ph2PO)-C6H9N2Ph)(C5Me5)Cl2]Cl (5) is more active than the other analogous complexes in the transfer hydrogenation (up to 81% ee). Graphical Abstract
    摘要 [Ru(η6-arene)(μ-Cl)Cl]2 和 Ir(η5-C5Me5)(μ-Cl)Cl]2 与一种新的基于离子液体的次膦酸盐配体 [(Ph2PO)-C6H9N2Ph ]Cl, (2) 得到 [Ru((Ph2PO)-C6H9N2Ph)(η6-p-cymene)Cl2]Cl (3), [Ru((Ph2PO)-C6H9N2Ph)(benzo)Cl2]Cl (4) 和 [ Ir((Ph2PO)-C6H9N2Ph)(C5Me5)Cl2]Cl (5),络合物。所有化合物均通过多核 NMR 和 IR 光谱以及元素分析的组合进行表征。此外,将 Ru(II) 和 Ir(III) 催化剂应用于使用 2-丙醇作为氢源的苯乙酮衍生物的不对称转移氢化。结果表明,在温和条件下可以得到具有良好活性(高达55%ee和99%转化率)的相应醇。尤其,[Ir((Ph2PO)-C6H9N2Ph)(C5Me5)Cl2]Cl
  • Phosphine ligands in the ruthenium-catalyzed reductive amination without an external hydrogen source
    作者:Maria Makarova、Oleg I. Afanasyev、Fedor Kliuev、Yulia V. Nelyubina、Maria Godovikova、Denis Chusov
    DOI:10.1016/j.jorganchem.2021.121806
    日期:2021.6
    A systematic study of the phosphine additives influence on the activity of a ruthenium catalyst in reductive amination without an external hydrogen source was carried out. [CymeneRuCl2]2 was used as a reference catalyst, and a broad set of phosphines including Alk3P, Alk2ArP, Ar3P and X3P was screened. Three complexes of general formula (Cymene)RuCl2PR3 were isolated in a pure form, and their catalytic
    在没有外部氢源的情况下,对膦添加剂对钌催化剂在还原胺化中的活性的影响进行了系统的研究。[CymeneRuCl 2 ] 2用作参考催化剂,并筛选出包括Alk 3 P,Alk 2 ArP,Ar 3 P和X 3 P在内的各种膦。以纯形式分离了三种通式(Cymene)RuCl 2 PR 3的配合物,并将其催化活性与原位进行了比较生成的复合体。发现具有电子受体基团的无阻碍的三芳基膦是最透视的活化剂,大约增加了催化剂的活性。六倍,Alk 2 ArP配体的影响较小,而三烷基膦使钌催化剂失活。
  • Copper-Catalyzed Carboxylation of Hydroborated Disubstituted Alkenes and Terminal Alkynes with Cesium Fluoride
    作者:Martin Juhl、Simon L. R. Laursen、Yuxing Huang、Dennis U. Nielsen、Kim Daasbjerg、Troels Skrydstrup
    DOI:10.1021/acscatal.6b03571
    日期:2017.2.3
    A protocol for the hydrocarboxylation of disubstituted alkenes and terminal alkynes providing access to different secondary carboxylic acids and malonic acid derivatives has been developed. This methodology relies on an initial hydroboration using 9-BBN followed by carboxylation with carbon dioxide in the presence of a copper catalyst and the additive, cesium fluoride. Different cyclohexene, styrene
    已经开发了用于双取代的烯烃和末端炔烃的加氢羧化的方案,其提供了获得不同的仲羧酸和丙二酸衍生物的途径。该方法依赖于首先使用9-BBN进行硼氢化,然后在铜催化剂和添加剂氟化铯的存在下用二氧化碳进行羧化。可以利用不同的环己烯,苯乙烯和二苯乙烯衍生物,并且炔可以良好的产率转化为它们相应的二羧酸。最后,使用开发的方法将六种不同的萜类化合物羧化。
  • Aldehydes as Alkylating Agents for Ketones
    作者:Sofiya A. Runikhina、Oleg I. Afanasyev、Klim Biriukov、Dmitry S. Perekalin、Martin Klussmann、Denis Chusov
    DOI:10.1002/chem.201904605
    日期:2019.12.18
    halides. The developed reductive alkylation reaction proceeds in the presence of the commercially available ruthenium catalyst [(cymene)RuCl2 ]2 (as low as 250 ppm) and carbon monoxide as the reducing agent. The reaction works well for a broad substrate scope, including aromatic and aliphatic aldehydes and ketones. It can be carried out without a solvent and often gives nearly quantitative yields of the
    提出了普通和无毒的醛作为酮烷基化的试剂,而不是致癌的烷基卤化物。所开发的还原烷基化反应在市售钌催化剂[(cymene)RuCl 2] 2(低至250ppm)和一氧化碳作为还原剂的存在下进行。该反应适用于广泛的底物范围,包括芳族和脂族醛和酮。它可以在没有溶剂的情况下进行,通常可以得到几乎定量的产物收率。这种简单,经济高效的方法不仅在实验室应用中而且对于工业界都很有希望,因为工业界将一氧化碳作为大规模的废品生产。
  • Reducing Characteristics of Borohydride Exchange Resin–CuSO<sub>4</sub>in Methanol
    作者:Tae Bo Sim、Nung Min Yoon
    DOI:10.1246/bcsj.70.1101
    日期:1997.5
    characteristics of borohydride exchange resin (BER)–CuSO4 (cat.) were studied in methanol at room temperature. Carbon–carbon double bonds conjugated with benzene or carbonyl group were more rapidly reduced than was the case with isolated double bonds. Carbonyl groups were readily reduced, whereas esters and amides were inert, and nitriles were slowly reduced. High chemoselectivity was also observed in halide reductions:
    在室温下在甲醇中研究了硼氢化物交换树脂 (BER)–CuSO4(催化剂)的还原特性。与苯或羰基共轭的碳碳双键比分离双键的还原速度更快。羰基很容易被还原,而酯和酰胺是惰性的,而腈则被缓慢还原。在卤化物还原中也观察到了高化学选择性:对溴氯苯和对溴碘苯分别被定量还原为氯苯和溴苯。脂肪族环氧化物对该试剂呈惰性;然而,氧化苯乙烯衍生物很容易还原成相应的脱氧产物。脂肪族叠氮化物在 6 小时内缓慢还原,而苯基叠氮化物在 1 小时内转化为苯胺。硝基环己烷在室温下被还原,但硝基苯、亚硝基苯、偶氮苯和偶氮苯需要升高的温度 (65 °C) 才能快速还原 (1 小时)。同样,N,N-二甲基苯胺N...
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定