chloro-butan-(R)-2-ol

• 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: chloro-butan-(R)-2-ol
• 英文别名: 1-chloro-butan-2-ol；(2R)-1-Chloro-2-butanol；(2R)-1-chlorobutan-2-ol
• 化学式: C₄H₉ClO
• 分子量: 108.568
• InChiKey: VNBFUGOVQMFIRN-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  2
• 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

• 作为产物：
  描述：

  丁氯醇 生成 chloro-butan-(R)-2-ol
  参考文献：
  名称：

  A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination

  摘要：

  A novel procedure for the generation of optically active ethyl 4-chloro-3-hydroxybutyrate using bacterial cells was developed. Ethyl (S)-4-chloro-3-hydroxybutyrate was prepared by Pseudomonas sp. OS-K-29, which stereoselectively assimilates 2,3-dichloro-1-propanol. The reaction was based on its kinetic dehalogenation for both enantiomers using the resting cells. The obtained 4-chloro-3-hydroxybutyrate rate had high enantiomeric excess of >98%, with a yield of 33% at the microbial resolution step. Moreover, several C4 compounds having the 4-chloro-3-hydroxyl function were also resolved and gave good enantiomeric purities (>95 %ee). Ethyl (R)-4-chloro-3-hydroxybutyrate was also obtained with high enantiomeric purity (>98 %ee) using the cells of Pseudomonas sp DS-K-NR818. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00410-7

文献信息

• A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates
  作者：Santosh Singh Thakur、Shu-Wei Chen、Wenji Li、Chang-Kyo Shin、Seong-Jin Kim、Yoon-Mo Koo、Geon-Joong Kim

  DOI：10.1016/j.jorganchem.2005.12.044

  日期：2006.4

  A new dinuclear chiral Co(salen) complexes bearing group 13 metals have been synthesized and characterized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity for the asymmetric ring opening of epoxides with H2O, chloride ions and carboxylic acids and consequently provide enantiomerically enriched terminal epoxides (>99% ee). It also catalyzes the asymmetric

  合成和表征了一种新型的带有第13族金属的双核手性Co（salen）配合物。易于制备的配合物对于环氧化物与H 2 O，氯离子和羧酸的不对称开环表现出非常高的催化反应活性和对映选择性，因此提供了对映体富集的末端环氧化物（> 99％ee）。它也催化开环产物的不对称环化，一步就可以制备出光学纯的末端环氧化物。均相双核手性Co（salen）已共价固定在MCM-41上。异质化的潜在好处包括需要非常简单的技术来促进催化剂的分离和可回收性。所描述的系统非常有效。
• Highly reactive and enantioselective kinetic resolution of terminal epoxides with H2O and HCl catalyzed by new chiral (salen)Co complex linked with Al
  作者：Santosh Singh Thakur、Wenji Li、Seong-Jin Kim、Geon-Joong Kim

  DOI：10.1016/j.tetlet.2005.02.012

  日期：2005.3

  hydrolytic kinetic resolution (HKR) of racemic terminal epoxides by new easily synthesized dimeric chiral (salen)Co bearing Al, provides a practical and straightforward method for the synthesis of enantiomerically enriched terminal epoxides (>99% ee) and diols. An inorganic acid, HCl is applied first time for the asymmetric ring opening reaction of terminal epoxides. Reactions are conveniently carried

  新的易于合成的带有Al的二聚手性（salen）Co的外消旋末端环氧化物的不对称水解动力学拆分（HKR），为合成对映异构体富集的末端环氧化物（> 99％ee）和二醇提供了一种实用而直接的方法。第一次使用无机酸HCl进行末端环氧化物的不对称开环反应。反应方便地在室温下在空气气氛下进行。
• A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination
  作者：Toshio Suzuki、Hideaki Idogaki、Naoya Kasai

  DOI：10.1016/0957-4166(96)00410-7

  日期：1996.11

  A novel procedure for the generation of optically active ethyl 4-chloro-3-hydroxybutyrate using bacterial cells was developed. Ethyl (S)-4-chloro-3-hydroxybutyrate was prepared by Pseudomonas sp. OS-K-29, which stereoselectively assimilates 2,3-dichloro-1-propanol. The reaction was based on its kinetic dehalogenation for both enantiomers using the resting cells. The obtained 4-chloro-3-hydroxybutyrate rate had high enantiomeric excess of >98%, with a yield of 33% at the microbial resolution step. Moreover, several C4 compounds having the 4-chloro-3-hydroxyl function were also resolved and gave good enantiomeric purities (>95 %ee). Ethyl (R)-4-chloro-3-hydroxybutyrate was also obtained with high enantiomeric purity (>98 %ee) using the cells of Pseudomonas sp DS-K-NR818. Copyright (C) 1996 Elsevier Science Ltd