3-Chloro-4-oxo-octanoic acid ethyl ester | 134443-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-Chloro-4-oxo-octanoic acid ethyl ester
• 英文别名: Ethyl 3-chloro-4-oxooctanoate
• CAS: 134443-88-2
• 化学式: C₁₀H₁₇ClO₃
• 分子量: 220.696
• InChiKey: CFBWDJXULUFEQI-UHFFFAOYSA-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：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Chloro-4-oxo-octanoic acid ethyl ester 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 、 Lipase P 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 65.75h， 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 磺酰氯 、 sodium hydride 、 三辛基氯化铵 、 对甲苯磺酸 作用下， 反应 35.5h， 生成 3-Chloro-4-oxo-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

• Method for the production of (r)-and (s)-8-chloro-6-hydroxy-octanic acid alkyl esters by enzymatic reduction
  申请人：Muller Michael

  公开号：US20050032180A1

  公开（公告）日：2005-02-10

  The invention relates to a method for the production of (R)- or (S)-8-chloro-6-hydroxyoctanoic acid alkyl esters of the general formula (R)-II or (S)-II in which R has the meaning C 1-4 -alkyl, from 8-chloro-6-oxooctanoic acid alkyl esters of the general formula I in which R has the above meaning, by enzymatic reduction using alcohol dehydrogenases, such as Lactobacillus brevis or Thermoanaerobium brokii , in the presence of cofactor regeneration systems. The resulting (R)- and (S)-8-chloro-6-hydroxyoctanoic acid esters can be converted in a known manner into (R)-α-lipoic acid and (S)-α-lipoic acid, respectively.

  本发明涉及一种生产通式为(R)-II或(S)-II的(R)-或(S)-8-氯-6-羟基辛酸烷基酯的方法。 其中 R 的含义为 C 1-4 -烷基，由通式 I 的 8-氯-6-氧代辛酸烷基酯组成 其中 R 具有上述含义，通过使用醇脱氢酶进行酶还原，如 乳酸杆菌 或 酵母菌 在辅因子再生系统存在的情况下进行酶还原。 得到的(R)-和(S)-8-氯-6-羟基辛酸酯可按已知方式分别转化为(R)-α-硫辛酸和(S)-α-硫辛酸。
• US7157253B2
  申请人：——

  公开号：US7157253B2

  公开（公告）日：2007-01-02
• 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.