(S)-1,3-dichloro-1-propanol

• 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)-1,3-dichloro-1-propanol
• 英文别名: (S)-2,3-dichloro-1-propanol；(S)-2,3-dichloropropan-1-ol；(S)-2,3-dichloropropanol；(2S)-2,3-Dichloropropan-1-OL
• 化学式: C₃H₆Cl₂O
• 分子量: 128.986
• InChiKey: ZXCYIJGIGSDJQQ-GSVOUGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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

• 作为反应物：
  描述：

  (S)-1,3-dichloro-1-propanol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以51%的产率得到右旋环氧氯丙烷
  参考文献：
  名称：

  Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media

  摘要：

  DOI：

  10.1021/ja00321a033
• 作为产物：
  描述：

  2,3-二氯-1-丙醇 在 phosphate buffer 、 甘油三丁酸酯 作用下， 反应 50.0h， 以82%的产率得到(S)-1,3-dichloro-1-propanol
  参考文献：
  名称：

  Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media

  摘要：

  DOI：

  10.1021/ja00321a033

文献信息

• Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine
  作者：Alexander H. Cleveland、Frank R. Fronczek、Rendy Kartika

  DOI：10.1021/acs.joc.7b03197

  日期：2018.3.16

  Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene–pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous

  在本文中，我们报道了一种基于三光气-吡啶活化将未活化的末端脂肪族环氧化物转化为烷基邻二氯乙烷的新型合成反应。我们的方法操作简单，容易被广泛的底物和保护基团所容忍。此外，这些温和的条件通常产生干净的反应混合物，该混合物在含水后处理时不含副产物。
• Directed Evolution Strategies for Enantiocomplementary Haloalkane Dehalogenases: From Chemical Waste to Enantiopure Building Blocks
  作者：Jan G. E. van Leeuwen、Hein J. Wijma、Robert J. Floor、Jan-Metske van der Laan、Dick B. Janssen

  DOI：10.1002/cbic.201100579

  日期：2012.1.2

  Waste not, want not: A carefully optimized directed evolution strategy was used to obtain two enantiocomplementary haloalkane dehalogenase variants that convert the toxic waste compound 1,2,3‐trichloropropane into either (R)‐ or (S)‐2,3‐dichloropropan‐1‐ol. The products can be converted into optically active epichlorohydrins that could be used for the preparation of various chiral pharmaceuticals.

  不浪费，不浪费：使用精心优化的定向进化策略来获得两个对映体互补的卤代烷脱卤酶变体，将有毒的废物化合物1,2,3-三氯丙烷转化为（R）-或（S）-2,3-二氯丙烷‐1‐ol。产物可以转化为旋光性表氯醇，其可以用于制备各种手性药物。
• Haloalkane dehalogenase catalysed desymmetrisation and tandem kinetic resolution for the preparation of chiral haloalcohols
  作者：Alja Westerbeek、Jan G.E. van Leeuwen、Wiktor Szymański、Ben L. Feringa、Dick B. Janssen

  DOI：10.1016/j.tet.2012.06.059

  日期：2012.9

  Six different bacterial haloalkane dehalogenases were recombinantly produced in Escherichia coli, purified, and used to catalyse the conversion of prochiral short-chain dihaloalkanes and a meso dihaloalkane, yielding enantioenriched haloalcohols. A two-reaction one-enzyme process was established in which the desymmetrisation of a dihaloalkane is followed by kinetic resolution of the chiral haloalcohol that is produced in the first step. In case of 1,3-dibromo-2-methylpropane and 1,3-dibromo-2-phenylpropane, an increase of the enantiomeric excess of the respective haloalcohol was observed in time, leading to ee values of >97%, with analytical yields of 24 and 52%, respectively. The results show that haloalkane dehalogenases can be used for the production of highly enantioenriched haloalcohols and that in some cases product enantiopurity can be improved by allowing a two-step one-enzyme tandem reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• 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
• A tandem enzyme reaction to produce optically active halohydrins, epoxides and diols
  作者：Jeffrey H. Lutje Spelberg、Johan E.T. van Hylckama Vlieg、Tjibbe Bosma、Richard M. Kellogg、Dick B. Janssen

  DOI：10.1016/s0957-4166(99)00308-0

  日期：1999.7