(3R,4R)-3-Chloro-4-hydroxy-octanoic acid ethyl ester

• 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: (3R,4R)-3-Chloro-4-hydroxy-octanoic acid ethyl ester
• 英文别名: ethyl (3R,4R)-3-chloro-4-hydroxyoctanoate
• 化学式: C₁₀H₁₉ClO₃
• 分子量: 222.712
• InChiKey: LAOBPWBCKQPHJT-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-Chloro-4-hydroxy-octanoic acid ethyl ester 在 吡啶 、 盐酸 、 copper(l) iodide 、 Lipase P 、 三乙胺 作用下， 反应 65.5h， 生成 (+)-反式威士忌内酯
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3AS,6aS)-Ethisolide, Whisky Lactone, and (−)-Avenaciolide

  摘要：

  Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydraxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (gamma S)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (+/-)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (gamma R)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.

  DOI：

  10.1021/jo970045r
• 作为产物：
  描述：

  叔丁基-戊酰基乙酸 在 吡啶 、 sodium tetrahydroborate 、 磺酰氯 、 Lipase P 、 sodium hydride 、 三辛基氯化铵 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 99.75h， 生成 (3R,4R)-3-Chloro-4-hydroxy-octanoic acid ethyl ester
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3AS,6aS)-Ethisolide, Whisky Lactone, and (−)-Avenaciolide

  摘要：

  Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydraxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (gamma S)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (+/-)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (gamma R)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.

  DOI：

  10.1021/jo970045r

文献信息

• Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3A<i>S</i>,6a<i>S</i>)-Ethisolide, Whisky Lactone, and (−)-Avenaciolide
  作者：Sadao Tsuboi、Jun-ichi Sakamoto、Hiroshi Yamashita、Takashi Sakai、Masanori Utaka

  DOI：10.1021/jo970045r

  日期：1998.2.1

  Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydraxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (gamma S)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (+/-)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (gamma R)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.