(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol | 13835-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol
• 英文别名: (R,R)-(+)-p-Menth-1-en-9-ol；(4R,8R)-p-Menth-1-en-9-ol；(4R,8R)-p-ment-1-en-9-ol；(+)-p-menth-1-en-9-ol；menth-1-en-9-ol；(+)-(4R,8R)-Δ¹-p-Menthen-9-ol；(+)-p-Menta-1-en-9-ol
• CAS: 13835-75-1；18479-68-0；26462-81-7；26462-90-8；70518-81-9；70518-83-1；13835-30-8
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: ZTYHGIAOVUPAAH-UWVGGRQHSA-N

物化性质

• 沸点：
  225.4±9.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)
• LogP：
  2.890 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2906199090

SDS

Name:	(+)-P-Menth-1-En-9-Ol, 97% Material Safety Data Sheet
Synonym:	None.
CAS:	13835-75-1

Section 1 - Chemical Product MSDS Name: (+)-P-Menth-1-En-9-Ol, 97% Material Safety Data Sheet
Synonym: None.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13835-75-1	(+)-p-menth-1-en-9-ol	97	237-548-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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SECTION 4 - FIRST AID MEASURES
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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SECTION 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Provide ventilation.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 13835-75-1: Personal Protective Equipment
Eyes:
Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Viscous liquid
Color: clear almost colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 115 - 116 deg C @ 10.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 103 deg C ( 217.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .941
Molecular Formula: C10H18O
Molecular Weight: 154.25

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SECTION 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 13835-75-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(+)-p-menth-1-en-9-ol - Not listed by ACGIH, IARC, or NTP.

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SECTION 12 - ECOLOGICAL INFORMATION

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SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

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SECTION 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 13835-75-1: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 13835-75-1 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 13835-75-1 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 1/18/1999 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol 在 吡啶 作用下， 生成 (S)-2-Methyl-6-((R)-4-methyl-cyclohex-3-enyl)-heptan-4-one
  参考文献：
  名称：

  Syntheses of Natural(+)-Juvabione, Its Enantiomer(-)-Juvabione, and Their Diastereoisomers (+)- and (-)-Epijuvabione

  摘要：

  DOI：

  10.1021/ja00705a641
• 作为产物：
  描述：

  甜橙提取物 在 吡啶 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 41.0h， 生成 (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-1-ol
  参考文献：
  名称：

  通过Norrish II裂解协议释放的光笼碳氢化合物，醛，酮，烯酮和羧酸和酯及以上：受控的光诱导香精释放

  摘要：

  摘要 描述了允许存储和释放以下小的挥发性有机分子的五类笼状芳香化合物：萜烯烃，醛，酮，迈克尔型α，β-不饱和烯酮以及羧酸和酯。这些笼状分子是通过羰基定向的氢转移过程的光激发和随后的C–C键裂解（Norrish II型）或通过重氮二氮脱氮而释放的。 描述了允许存储和释放以下小的挥发性有机分子的五类笼状芳香化合物：萜烯烃，醛，酮，迈克尔型α，β-不饱和烯酮以及羧酸和酯。这些笼状分子是通过羰基定向的氢转移过程的光激发和随后的C–C键裂解（Norrish II型）或通过重氮二氮脱氮而释放的。

  DOI：

  10.1055/s-0036-1588645

文献信息

• 9-Borabicyclo[3.3.2]decanes and the Asymmetric Hydroboration of 1,1-Disubstituted Alkenes
  作者：Ana Z. Gonzalez、José G. Román、Eduvigis Gonzalez、Judith Martinez、Jesus R. Medina、Karl Matos、John A. Soderquist

  DOI：10.1021/ja803119p

  日期：2008.7.1

  The syntheses of the optically pure asymmetric hydroborating agents 1 (a, R = Ph; b, R = TMS) in both enantiomeric forms are reported. These reagents are effective for the hydroboration of cis-, trans- and trisubstituted alkenes. More significantly, they exhibit unprecedented levels of selectivity in the asymmetric hydroboration of 1,1-disubstituted alkenes (28-92% ee), a previously unanswered challenge

  报道了两种对映体形式的光学纯不对称硼氢化剂 1 (a, R = Ph; b, R = TMS) 的合成。这些试剂对顺式、反式和三取代烯烃的硼氢化反应有效。更重要的是，它们在 1,1-二取代烯烃 (28-92% ee) 的不对称硼氢化反应中表现出前所未有的选择性，这是该试剂控制过程近 50 年历史中从未解决的挑战。例如，α-甲基苯乙烯与 1a 的硼氢化反应在 78% ee（参见 Ipc2BH，5% ee）中产生相应的醇 6f。中间加合物 5 的 Suzuki 偶联非常有效地（50-84%）产生非外消旋产物 7，而不会损失光学纯度。
• A Chemoenzymatic, Preparative Synthesis of the Isomeric Forms ofp-Menth-1-en-9-ol: Application to the Synthesis of the Isomeric Forms of the Cooling Agent 1-Hydroxy-2,9-cineole
  作者：Stefano Serra、Claudio Fuganti、Francesco G. Gatti

  DOI：10.1002/ejoc.200701010

  日期：2008.2

  A preparative-scale synthesis of the four p-menth-1-en-9-ol isomers 2a–5a has been achieved by means of two chemoenzymatic processes. Both synthetic pathways start from the enantiomeric forms of limonene that are converted into p-mentha-1,8-dien-9-al isomers 12 and 15. The baker's yeast mediated reduction of the latter aldehydes afforded compounds 3a and 5a, respectively, with very high enantioselectivity

  四种 p-menth-1-en-9-ol 异构体 2a-5a 的制备规模合成已通过两种化学酶促过程实现。两种合成途径都从柠檬烯的对映体形式开始，将其转化为 p-mentha-1,8-dien-9-al 异构体 12 和 15。面包酵母介导的后一种醛的还原分别提供了化合物 3a 和 5a，与非常高的对映选择性。此外，12 和 15 的化学还原分别得到对映纯的非对映异构体 2a/3a 和 4a/5a 的混合物。PPL（猪胰腺脂肪酶）介导后一种混合物的分辨率，然后对衍生物 2b-5b 进行分级结晶，从而获得对映异构和非对映异构纯醇 2a-5a。然后，化合物 2a-5a 已被用作制备凉味剂 1-羟基-2,9-桉树脑 (6-9) 的四种异构体的起始材料。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• ?1-p-Menthen-9-al, ein Bestandteil des bulgarischen Rosen�ls
  作者：G. Ohloff、W. Giersch、K. H. Schulte-Elte、E. sz. Kovats

  DOI：10.1002/hlca.19690520614

  日期：——

  Als einer der Bestandteile des riechenden Prinzips vom bulgarischen Rosenöl wurde (+)-δ1-p-Menthen-9-al erkannt. Seine Stereochemie wurde zusammen mit einer Reihe verwandter Verbindungen festgelegt. 2, 8 und 10 besitzen danach die 4 R, 8 R-Konfiguration, während die Chiralitätszentren der Verbindungen 3, 9 und 11 mit 4 R, 8 S bezeichnet werden müssen. Demzufolge konnte für 4, 5, 12 und 14 die 8 R-

  ALS einer DER Bestandteile DES riechenden Prinzips VOM bulgarischenRosenölwurde（+） - δ 1 - p -Menthen -9-人erkannt。Seine Stereochemie wurde zusammen mit einer Reihe verwandter Verbindungen festgelegt。2，8 UND 10 besitzen danach模4 - [R，8 - [R -Konfiguration，während死ChiralitätszentrenDER Verbindungen 3，9 UND 11麻省理工4 - [R，8小号bezeichnet werdenmüssen。Demzufolge konnte献给4，5，12 UND 14模8 - [R - ，毛皮6，7，13 UND15死8
• A new class of monocyclic diterpenes from kraenzlin. (Myoporaceae)
  作者：P.G. Forster、E.L. Ghisalberti、P.R. Jefferies

  DOI：10.1016/s0040-4020(01)86839-3

  日期：1987.1

  Three diterpene acids, representing a new class of monocyclic diterpenes, have been isolated from E. foliosissima Kraenzlin. (Myoporaceae). Chemical and spectroscopic evidence is presented for their structure and absolute configuration. These diterpenes can be considered as isoprenologues of the bisabolene sesquiterpenes.

  从大肠埃希氏菌中分离出了代表一类新的单环二萜的三种三萜酸。（肌科）。化学和光谱学证据表明它们的结构和绝对构型。这些二萜可以被认为是双sabolene倍半萜的异戊二烯。
• Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans
  作者：Z. Y. Wei、D. Wang、J. S. Li、T. H. Chan

  DOI：10.1021/jo00285a025

  日期：1989.11

表征谱图