(S)-(+)-1-辛烯-3-醇 | 3391-86-4

• 物质功能分类: 香精与香料 - 合成香料 - 醇类香料
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-(+)-1-辛烯-3-醇
• 中文别名: (S)-松茸醇；(S)-1-辛烯-3-醇
• 英文名称: (S)-oct-1-en-3-ol
• 英文别名: (+)-(S)-1-octene-3-ol；(S)-matsutake alcohol；(S)-(+)-1-octen-3-ol；(3S)-oct-1-en-3-ol；(S)-1-Octene-3-ol；(S)-1-octen-3-ol
• CAS: 3391-86-4；3687-48-7；50999-79-6；24587-53-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: VSMOENVRRABVKN-MRVPVSSYSA-N

物化性质

• 熔点：
  -49°C
• 沸点：
  84-85 °C/25 mmHg (lit.)
• 密度：
  0.837 g/mL at 20 °C 0.83 g/mL at 25 °C (lit.)
• 闪点：
  142 °F
• 溶解度：
  乙腈（微溶）、氯仿、乙酸乙酯（微溶）
• LogP：
  2.64
• 保留指数：
  962

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22,R20/21/22,R36/38
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险品运输编号：
  2810
• RTECS号：
  RH3300000
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Name:	R-(-)-1-Octen-3-Ol 99% Material Safety Data Sheet
Synonym:	None Known
CAS:	3687-48-7

Section 1 - Chemical Product MSDS Name:R-(-)-1-Octen-3-Ol 99% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3687-48-7	R-(-)-1-Octen-3-Ol	99%	unlisted

Hazard Symbols: XN
Risk Phrases: 21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. May cause cardiac disturbances. The toxicological properties of this substance have not been fully investigated. May cause central nervous system depression.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May cause cardiac abnormalities. Inhalation at high concentrations may cause CNS depression and asphixiation.
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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Combustible material; may burn but does not ignite readily. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Avoid runoff into storm sewers and ditches which lead to waterways.
Clean up spills immediately, observing precautions in the Protective Equipment section. Absorb spill using an absorbent, non-combustible material such as earth, sand, or vermiculite. Do not use combustible materials such as sawdust. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation.
Storage:
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3687-48-7: 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: Liquid
Color: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: 245 deg C ( 473.00 deg F)
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: insoluble
Specific Gravity/Density:
Molecular Formula: C8H16O
Molecular Weight: 128.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, 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# 3687-48-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
R-(-)-1-Octen-3-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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 21/22 Harmful in contact with skin and if
swallowed.
Safety Phrases:
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 3687-48-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3687-48-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3687-48-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

理化性质

1-辛烯-3-醇是一种脂肪族不饱和醇，外观为无色至淡黄色油状液体。它具有独特的蘑菇、薰衣草、玫瑰和干草香气。这种化合物不溶于水，但可以溶解在乙醇等有机溶剂中。

合成

向四氢吡喃基醚（5 mmol）与CH3OH（25 mmol）的混合物中加入TCCA（0.12 g，0.5 mmol）。将混合物室温搅拌适当时间后（表1），进行反应监测（GC或TLC）。完成反应后，向反应混合物中添加CH2Cl2（50 mL）。所得混合物用10%的Na2S2O3水溶液洗涤，然后倾析。有机相使用无水MgSO4干燥，并在减压下蒸发溶剂以获得高产率的羟基化合物1-辛烯-3-醇。分离产物的光谱数据（IR、NMR）与真实样品报告的数据一致。

图 1-辛烯-3-醇的合成路线

含量分析

按照GT-10-4中的极性柱进行气相色谱法测定含量。

毒性

GRAS (FEMA)。

使用限量

食品类别	FEMA(mg/kg)
软饮料	0.20
冷饮	1.0
糖果	2.0
焙烤食品	6.0
调味品	6.0
沙司	6.0

适度为限 (FDA §172.515, 2000)。

食品添加剂最大允许使用量及最大允许残留量标准

根据GB 2760-1996，1-辛烯-3-醇被规定为允许使用的食用香料。主要用于配制蘑菇和泥土味等型香精。

化学性质

1-辛烯-3-醇是一种无色液体，不溶于水但可溶于乙醇等有机溶剂。

用途

GB 2760-1996规定其为允许使用的食用香料。主要用于配制蘑菇和泥土味等型香精。也可用于日化产品和食用香精中，并可用于人造精油、重组精油或制成酯类香料。

生产方法

由戊基溴化镁与丙烯醛反应而得。

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-辛烯-3-醇 在 咪唑 、 盐酸 、 Hoveyda-Grubbs catalyst second generation 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 13.5h， 生成 地诺前列素
  参考文献：
  名称：

  PGF的总合成2α和-6,15-二酮PGF 1α和6-酮PGF的正式合成1α经由三组分偶联

  摘要：

  PGF的不对称全合成2α和-6,15-二酮PGF 1α和6-酮PGF的正式合成1α从一个共同的关键中间体进行说明。由（R）-4-甲硅烷氧基-2-环戊烯酮通过三组分偶联反应制备具有中间体的关键中间体，该中间体具有手性的环戊烷主链，该手性环戊烷主链具有合适的官能团且两侧链具有所需的立体化学。维悌希反应，野崎-桧山-岸（NHK）耦合和交叉复分解完成PGF的合成2α，-6,15-二酮PGF 1α和6-酮PGF 1α。

  DOI：

  10.1016/j.tet.2019.130593
• 作为产物：
  描述：

  正戊基溴化镁 在 氢喹啉 9-菲基醚 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-(+)-1-辛烯-3-醇
  参考文献：
  名称：

  通过连续的不对称二羟基化（AD）和Peterson烯化反应由烯丙基硅烷合成旋光仲烯丙基醇

  摘要：

  可以通过连续不对称二羟基化和彼得森烯化反应由烯丙基硅烷制备旋光仲烯丙基醇。还讨论了三烷基甲硅烷基对乙烯基和烯丙基硅烷上AD反应结果的影响。

  DOI：

  10.1016/s0040-4039(00)60454-9

文献信息

• Allylic Etherification via Ir(I)/Zn(II) Bimetallic Catalysis
  作者：Justin P. Roberts、Chulbom Lee

  DOI：10.1021/ol0508328

  日期：2005.6.1

  [reaction: see text] An efficient allylic etherification of aliphatic alcohols with allylic carbonates has been achieved by an iridium catalysis using stoichiometric zinc alkoxides or a two-component bimetallic catalytic system where the Ir(I) catalyst acts on allylic carbonates to generate electrophiles while aliphatic alcohols are separately activated by Zn(II) coordination to function as nucleophilies

  [反应：见正文]通过使用化学计量的醇锌或二组分双金属催化体系的铱催化，实现了脂肪族醇与碳酸烯丙酯的有效烯丙基醚化反应，其中Ir（I）催化剂作用于碳酸烯丙酯以生成亲电子试剂，而脂族醇通过Zn（II）配位分别激活，以发挥亲核作用。该反应具有完全的区域特异性，并且可以耐受各种官能团。
• Biocatalytic deuterium- and hydrogen-transfer using over-expressed ADH-‘A’: enhanced stereoselectivity and²H-labeled chiral alcohols
  作者：Klaus Edegger、Christian C. Gruber、Tina M. Poessl、Sabine R. Wallner、Iván Lavandera、Kurt Faber、Frank Niehaus、Juergen Eck、Reinhold Oehrlein、Andreas Hafner、Wolfgang Kroutil

  DOI：10.1039/b602487d

  日期：——

  Employing the over-expressed highly organic solvent tolerant alcohol dehydrogenase ADH-‘A’ from Rhodococcus ruber DSM 44541, versatile building blocks, which were not accessible by the wild type catalyst, were obtained in > 99% e.e.; furthermore, employing d8-2-propanol as deuterium source, stereoselective biocatalytic deuterium transfer was made feasible to furnish enantiopure deuterium labeled sec-alcohols on a preparative scale employing a single enzyme.

  利用来自红球菌DSM 44541的高度有机溶剂耐受性乙醇脱氢酶ADH-“A”进行过量表达，获得了通过野生型催化剂无法获得的多种高效构件，其对映体纯度超过99%；此外，采用d8-2-丙醇作为氘源，实现了利用单一酶在制备规模上进行立体选择性生物催化氘转移，从而制备了手性纯氘标记的二级醇。
• Vinyl anion equivalent V. Asymmetric synthesis of allylic alcohols using chiral 2-(trialkylsilyl)ethyl sulfoxides
  作者：Shinya Kusuda、Yoshio Ueno、Takeshi Toru

  DOI：10.1016/s0040-4020(01)80816-4

  日期：1994.1

  Both enantiomers of optically pure secondary allylic alcohols can be conveniently prepared by the diastereoselective reaction of the α-sulfinyl carbanion of p-tolyl 2-(trialkylsilyl)ethyl sulfoxides or tert-butyl 2-(trimethylsilyl)ethyl sulfoxide with aldehydes followed by either fluoride-induced desilylsulfinylation or thermal elimination of the sulfinyl group.

  光学纯的仲烯丙基醇的两种对映异构体可通过对甲苯基2-（三烷基甲硅烷基）乙基亚砜或叔丁基2-（三甲基甲硅烷基）乙基亚砜的α-亚磺酰基碳负离子与醛随后进行氟化的非对映选择性反应方便地制备。-诱导的亚甲硅烷基亚磺酰基化或亚氨基的热消除。
• Sequential Pd(0)-, Rh(I)-, and Ru(II)-Catalyzed Reactions in a Nine-Step Synthesis of Clinprost
  作者：Emma E. Nagy、I. F. Dempsey Hyatt、Kristen E. Gettys、Shawn T. Yeazell、Stephen K. Frempong、Mitchell P. Croatt

  DOI：10.1021/ol303402e

  日期：2013.2.1

  A step-economical synthesis of clinprost is reported that concludes with 3 different transition metal-catalyzed reactions: Pd-catalyzed decarboxylation with allylic rearrangement, Rh-catalyzed diene-ene [2+2+1] reaction, and Ru-catalyzed cross-metathesis reaction. The complexity bestowed to the molecule from these reactions converts a readily accessible ester to clinprost without using protecting groups

  报道了clinprost的分步经济合成，该合成以3种不同的过渡金属催化反应结束：Pd催化烯丙基重排脱羧，Rh催化二烯-烯[2 + 2 + 1]反应和Ru催化的交叉复分解反应。通过这些反应赋予分子的复杂性将易于获得的酯转化为克林前列素，而仅在总共9个步骤中不使用保护基。
• Clinprost, Isocarbacyclin And Analogs Thereof And Methods Of Making The Same
  申请人：The University Of North Carolina At Greensboro

  公开号：US20140114086A1

  公开（公告）日：2014-04-24

  In one aspect, methods of synthesizing clinprost, isocarbacyclin and analogs thereof are described herein which, in some embodiments, permit an abbreviated synthetic pathway in comparison to one or more prior synthetic methods. By providing a compact synthetic scheme, methods described herein can reduce cost, waste and time of clinprost and isocarbacyclin synthesis while facilitating the development and investigation of analogs of these compounds.

  在某些方面，本文描述了一种合成克林前列素（clinprost）、异卡巴环素（isocarbacyclin）及其类似物的方法，这些方法在某些实施方式中相对于一个或多个先前的合成方法允许缩短的合成途径。通过提供简洁的合成方案，本文描述的方法可以减少克林前列素和异卡巴环素合成的成本、废物和时间，同时促进这些化合物的类似物的开发和研究。