Ethyl (2S,3S)-3-chloro-2-hydroxyheptanoate | 113524-96-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (2S,3S)-3-chloro-2-hydroxyheptanoate
• CAS: 113524-96-2
• 化学式: C₉H₁₇ClO₃
• 分子量: 208.685
• InChiKey: YBTKZQSEKYUADR-JGVFFNPUSA-N

物化性质

• 沸点：
  278.7±20.0 °C(predicted)
• 密度：
  1.097±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Ethyl 2-chloro-2,3-epoxyheptanoate 在 aluminum oxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 xylene 为溶剂， 反应 3.17h， 生成 Ethyl (2S,3S)-3-chloro-2-hydroxyheptanoate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure

  摘要：

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00529-0

文献信息

• A Practical Synthesis of Chiral 3-Chloro-2-hydroxyalkanoates and 2,3-Epoxyalcohols
  作者：Sadao Tsuboi、Hiroyuki Furutani、Masanori Utaka、Akira Takeda

  DOI：10.1016/s0040-4039(00)96187-2

  日期：1987.1
• Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters
  作者：Sadao Tsuboi、Hiroyuki Furutani、Mohammad Hafeez Ansari、Takashi Sakai、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00054a036

  日期：1993.1

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.
• Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure
  作者：Sadao Tsuboi、Nobuyuki Yamafuji、Masanori Utaka

  DOI：10.1016/s0957-4166(96)00529-0

  日期：1997.2

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.