(2R,5R)-(+)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮 | 390766-89-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2R,5R)-(+)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮
• 中文别名: (2R,5R)-(+)-2-叔丁基-3-甲基-5苄基-4-咪唑啉酮；(2R,5R)-2-叔丁基-3-甲基-5-苯基甲基-4-咪唑烷酮；(2R,5R)-(+)- 2-叔丁基-3-甲基-5 苄基-4-咪唑啉酮
• 英文名称: (2R,5R)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
• 英文别名: (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone；(2R,5R)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one
• CAS: 390766-89-9
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: SKHPYKHVYFTIOI-TZMCWYRMSA-N

物化性质

• 熔点：
  93-100°C
• 沸点：
  378.0±35.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : (2R,5R)-(+)-2-tert-Butyl-3-methyl-5-benzyl-4-
imidazolidinone
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. : 390766-89-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : (2R,5R)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone
Formula : C15H22N2O
Molecular Weight : 246,35 g/mol
CAS-No. : 390766-89-9
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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

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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, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
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.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
Colour: white, beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 93 - 100 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,236
octanol/water
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

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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
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available

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SECTION 12: Ecological information
Toxicity
no data available
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

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2R,5R)-(+)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到(R)-2-tert-butyl-4-benzyl-1-methyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  使用高价碘试剂的对映选择性有机催化环氧化

  摘要：

  据报道，使用咪唑烷酮催化剂1可以使α，β-不饱和醛发生有机催化，不对称环氧化，这是参与1，4-杂合物加成反应的高价碘试剂的一个罕见例子。通过从亚碘碘烷源缓慢释放碘代苯来开发“内部注射泵”效应，可在缺电子烯烃的不对称环氧化中提供高水平的反应效率和对映体控制。进行了15 N NMR研究，以阐明在原型氧化剂存在下导致催化剂耗竭的反应途径。这些NMR研究也为亚氨基碘烷作为内部缓释氧化剂的应用提供了机理基础，以规避这些催化剂的消耗途径。

  DOI：

  10.1016/j.tet.2006.07.055
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 在 iron(III) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 120.0h， 生成 (2R,5R)-(+)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮
  参考文献：
  名称：

  通过有机催化 Diels-Alder 反应高度对映选择性地获得大麻素型三环。

  摘要：

  经过对苯并吡喃的多米诺反应，产物被用作路易斯酸催化和有机催化狄尔斯-阿尔德反应的起始材料，以建立三环体系。在本文中，通过使用咪唑烷酮催化剂获得了高达 96% 对映体过量的不对称诱导。这种方法可用于在众多天然产物中构建三环体系，特别是四氢大麻酚 (THC) 的支架是最具代表性的一种。与其他已发表的方法相比，需要与前体中预先存在的环己烷部分缩合以获得异质三环系统，而我们提出了一种基于灵活模块合成的大麻素衍生物的新策略。

  DOI：

  10.3762/bjoc.8.160
• 作为试剂：
  描述：

  苯丙醛 、 p-nitrobenzenesulfonyl azide 在 (2R,5R)-(+)-2-叔丁基-3-甲基-5-苄基-4-咪唑烷酮 、 高氯酸 作用下， 以 水 为溶剂， 反应 24.0h， 以89.6%的产率得到
  参考文献：
  名称：

  磺酰叠氮化物对醛的对映选择性有机催化α-磺酰胺化

  摘要：

  描述了使用麦克米兰的第二代咪唑烷酮催化剂和邻硝基苯磺酰基叠氮化物对非支链醛的对映选择性有机催化α-磺酰胺化反应。反应是高度立体选择性的（89.9–96.3％ee），产率高达71％。发现醛结构与产物产率之间存在强相关性，其中3-芳基丙醛提供最佳结果。介绍了在功能化氨基酸合成中的应用。

  DOI：

  10.1016/j.tetlet.2017.10.063

文献信息

• Transfer of 1-Alkenyl Groups between Secondary Amines. Relative Stability and Reactivity of Enamines from Popular Organocatalysts
  作者：Héctor Carneros、Dani Sánchez、Jaume Vilarrasa

  DOI：10.1021/ol501044u

  日期：2014.6.6

  Enamines from 3-methylbutanal and several Pro- and Phe-derived secondary amines were prepared in DMSO-d6, CD3CN, and CDCl3. For the first time, the relative thermodynamic stabilities of these and other enamines were compared, and rapid exchanges of 1-alkenyl groups were demonstrated. Competition experiments showed that the most favored enamines (without significant steric inhibition of resonance) react

  在DMSO- d 6，CD 3 CN和CDCl 3中制备了3-甲基丁醛的烯胺以及几种Pro和Phe衍生的仲胺。第一次，比较了这些和其他烯胺的相对热力学稳定性，并证明了1-烯基的快速交换。竞争实验表明，最喜欢的烯胺（对共振没有明显的空间抑制作用）与亲电子试剂反应更快。
• CATALYST FOR ASYMMETRIC HYDROGENATION
  申请人：MAEDA Hironori

  公开号：US20100324338A1

  公开（公告）日：2010-12-23

  This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an α,β-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

  这项发明旨在通过对α，β-不饱和羰基化合物进行选择性不对称加氢，特别是通过对柠檬醛、香叶醛或柠檬醛进行选择性不对称加氢，从而提供用作香料或香精的有用的光学活性香茅醛的催化剂，该香茅醛是一种光学活性羰基化合物；以及生产相应的光学活性羰基化合物的方法。该发明涉及一种用于不对称加氢α，β-不饱和羰基化合物的催化剂，其包括来自周期表第8至第10族金属中至少一种金属的粉末，或者至少一种来自周期表第8至第10族金属的金属负载物质，该金属负载在一种支撑物上，还包括光学活性的含氮环化合物和酸。
• Ring-Closing Metathesis of Allylsilanes/Electrophilic Desilylation To Prepare <i>exo</i>-Methylidenecycloalkanes. Short Syntheses of Teucladiol and Poitediol
  作者：Matthew S. Dowling、Christopher D. Vanderwal

  DOI：10.1021/ja906241w

  日期：2009.10.28

  A general strategy for the synthesis of exo-methylidenecycloalkanes, which are salient features of many terpenoid natural products, is presented. Ring-closing alkene metathesis of allylsilanes provides intermediates that can be protodesilylated with alkene transposition to afford the exocyclic alkene; alternatively, the reactivity of the cyclic allylsilane intermediate can be harnessed to introduce

  介绍了合成外亚甲基环烷烃的一般策略，这是许多萜类天然产物的显着特征。烯丙基硅烷的闭环烯烃复分解反应提供了中间体，这些中间体可以通过烯烃转位进行原脱甲硅烷化，得到环外烯烃；或者，可以利用环状烯丙基硅烷中间体的反应性来引入烯丙基官能团。这两种反应模式分别在倍半萜烯天然产物 teucladiol 和 poitediol 的短合成中展示。
• Hydride reduction of alpha, beta-unsaturated carbonyl compounds using chiral organic catalysts
  申请人：MacMillan David

  公开号：US20080125310A1

  公开（公告）日：2008-05-29

  Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-hydride reduction of an α,β-unsaturated carbonyl compound. The α,β-unsaturated carbonyl compound may be an aldehyde or cyclic ketone, and the hydride donor may be a dihydropyridine. The reaction is enantioselective, and proceeds with a variety of hydride donors, catalysts, and substrates. The invention also provides compositions effective in carrying out the 1,4-hydride addition of α,β-unsaturated carbonyl compounds.

  非金属手性有机催化剂被用于催化α,β-不饱和羰基化合物的1,4-氢化还原反应。α,β-不饱和羰基化合物可以是醛或环状酮，氢化供体可以是二氢吡啶。该反应是对映选择性的，并且可以使用多种氢化供体、催化剂和底物进行。本发明还提供了在进行α,β-不饱和羰基化合物的1,4-氢化加成反应时有效的组合物。
• 6-chloro-3-(phenyl-d5)-inden-1-one and use thereof
  申请人：H. LUNDBECK A/S

  公开号：US20150336867A1

  公开（公告）日：2015-11-26

  The present invention discloses the compound 6-chloro-3-(phenyl-d 5 )-inden-1-one (I) and routes of synthesis to obtain (I). In a further aspect the present invention discloses the use of (I) for the synthesis of (S)-6-chloro-3-(phenyl-d 5 )-indan-1-one.

  本发明揭示了化合物6-氯-3-(苯基-d5)-茚-1-酮(I)及其合成路线。此外，本发明还揭示了利用(I)合成(S)-6-氯-3-(苯基-d5)-茚-1-酮的用途。