(S)-1-bromo-2-octanol | 213893-15-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-1-bromo-2-octanol
• 英文别名: (2S)-1-bromooctan-2-ol
• CAS: 213893-15-3
• 化学式: C₈H₁₇BrO
• 分子量: 209.126
• InChiKey: UOOOQHMFMRVNJN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-bromo-2-octanol 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以92%的产率得到S(-)-1,2-环氧辛烷
  参考文献：
  名称：

  的对映体纯脂族终端（的实用两步合成小号）的基础上-Epoxide的Haloalkanones减少与“设计的细胞”

  摘要：

  开发了一种实用的生物催化方法，其通过用带有乙醇脱氢酶和葡萄糖脱氢酶的重组全细胞对映选择性还原相应的酮来合成作为环氧化物前体的脂肪族β-卤代（S）-醇。生物转化在高达208 g / L的高底物浓度下运行，并提供（S）-β-卤代醇，其高转化率> 95％，对映选择性> 99％ee。碱诱导的β-卤代醇中间体的环化反应以高收率和对映体纯度（> 99％ee）得到所需的（S）-环氧化物。

  DOI：

  10.1002/adsc.200700244
• 作为产物：
  描述：

  1-溴辛烷-2-醇 生成 (S)-1-bromo-2-octanol
  参考文献：
  名称：

  Enantiomerically enriched bifunctional sec-alcohols prepared by Candida antarctica lipase B catalysis. Evidence of non-steric interactions

  摘要：

  Transesterification catalysed by Candida antarctica lipase B was used for the preparation of enantiomerically enriched bifunctional sec-alcohols. The enantiomeric ratio, E, for 3-butyn-2-ol was increased from 1.3 to over 500 by adding an easily removable protecting group. Kinetic resolution of bromohydrins and chlorohydrins bearing a halogen on the large substituent showed high enantioselectivity (E>80). On the other hand, halohydrins with the halogen on the medium group showed low E. Large differences in enantioselectivity were found by substituting the halogen atom of 1-halo-2-alkanols by a methyl group. These differences corresponded to more than 2 kcal mol(-1) and were ascribed to non-steric interactions. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00004-9

文献信息

• Chemo- and Stereodivergent Preparation of Terminal Epoxides and Bromohydrins through One-Pot Biocatalysed Reactions: Access to Enantiopure Five- and Six-Membered N-Heterocycles
  作者：Fabricio R. Bisogno、Aníbal Cuetos、Alejandro A. Orden、Marcela Kurina-Sanz、Iván Lavandera、Vicente Gotor

  DOI：10.1002/adsc.201000353

  日期：——

  Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one‐pot starting from the corresponding α‐bromo ketones through alcohol dehydrogenase (ADH)‐catalysed processes adding an organic co‐solvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5–10) epoxides

  从相应的α-溴代酮开始，通过醇脱氢酶（ADH）催化的过程，通过添加有机助溶剂并适当调节介质的pH和温度，在一锅中化学选择性地合成了不同的对映纯末端环氧化物或溴代醇。因此，在碱性条件下（pH 9.5-10），在中性pH值下可获得对映纯的溴代醇，而环氧化物是主要产物。此外，通过简单地选择生物催化剂，可以实现化学和立体发散转化，从而获得例如对映体纯的脯氨醇或哌啶子蛋白-3-醇。
• Preparation of (S)-1-Halo-2-octanols Using Ionic Liquids and Biocatalysts
  作者：Mireia Oromí-Farrús、Jordi Eras、Núria Sala、Mercè Torres、Ramon Canela

  DOI：10.3390/molecules14104275

  日期：——

  Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym 435), Rhizomucor miehei (Lipozyme IM), and "resting cells" from a Rhizopus

  (S)-1-氯-2-辛醇和(S)-1-溴-2-辛醇的制备通过使用生物催化剂的卤代醇棕榈酸酯的酶促水解来进行。卤代醇棕榈酸酯通过各种方法从棕榈酸和 1,2-辛二醇制备。使用来自南极假丝酵母 (Novozym 435)、米黑根霉 (Lipozyme IM) 的脂肪酶和来自不产生霉菌毒素的米根霉菌株的“静息细胞”进行串联水解。描述了酶和反应介质对卤代醇酯异构体混合物选择性水解的影响。Novozym 435 允许在 [BMIM][PF(6)] 中在 40 摄氏度反应 1-3 小时后制备 (S)-1-氯-2-辛醇和 (S)-1-溴-2-辛醇。
• Enantiomerically enriched bifunctional sec-alcohols prepared by Candida antarctica lipase B catalysis. Evidence of non-steric interactions
  作者：Didier Rotticci、Christian Orrenius、Karl Hult、Torbjörn Norin

  DOI：10.1016/s0957-4166(97)00004-9

  日期：1997.2

  Transesterification catalysed by Candida antarctica lipase B was used for the preparation of enantiomerically enriched bifunctional sec-alcohols. The enantiomeric ratio, E, for 3-butyn-2-ol was increased from 1.3 to over 500 by adding an easily removable protecting group. Kinetic resolution of bromohydrins and chlorohydrins bearing a halogen on the large substituent showed high enantioselectivity (E>80). On the other hand, halohydrins with the halogen on the medium group showed low E. Large differences in enantioselectivity were found by substituting the halogen atom of 1-halo-2-alkanols by a methyl group. These differences corresponded to more than 2 kcal mol(-1) and were ascribed to non-steric interactions. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Practical Two-Step Synthesis of an Enantiopure Aliphatic Terminal (S)-Epoxide Based on Reduction of Haloalkanones with “Designer Cells”
  作者：Albrecht Berkessel、Claudia Rollmann、Francoise Chamouleau、Stefanie Labs、Oliver May、Harald Gröger

  DOI：10.1002/adsc.200700244

  日期：2007.12.10

  synthesis of aliphatic β-halogenated (S)-alcohols as epoxide precursors by means of an enantioselective reduction of the corresponding ketones with recombinant whole cells, bearing an alcohol dehydrogenase and a glucose dehydrogenase, was developed. The biotransformations operate at high substrate concentrations of up to 208 g/L, and afford the (S)-β-halohydrins with both high conversions of >95 % and enantioselectivities

  开发了一种实用的生物催化方法，其通过用带有乙醇脱氢酶和葡萄糖脱氢酶的重组全细胞对映选择性还原相应的酮来合成作为环氧化物前体的脂肪族β-卤代（S）-醇。生物转化在高达208 g / L的高底物浓度下运行，并提供（S）-β-卤代醇，其高转化率> 95％，对映选择性> 99％ee。碱诱导的β-卤代醇中间体的环化反应以高收率和对映体纯度（> 99％ee）得到所需的（S）-环氧化物。