ethyl 3-chloro-4-oxododecanoate | 134443-90-6

• 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: ethyl 3-chloro-4-oxododecanoate
• CAS: 134443-90-6
• 化学式: C₁₄H₂₅ClO₃
• 分子量: 276.804
• InChiKey: IEAXYEILBJVERN-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±22.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  18.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-chloro-4-oxododecanoate 在 吡啶 、 sodium tetrahydroborate 、 Lipase P 作用下， 以 乙醇 为溶剂， 反应 64.17h， 生成 (3S,4S)-4-Acetoxy-3-chloro-dodecanoic 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

• Tsuboi, Sadao; Sakamoto, Jun-ichi; Sakai, Takashi, Chemistry Letters, 1989, p. 1427 - 1428
  作者：Tsuboi, Sadao、Sakamoto, Jun-ichi、Sakai, Takashi、Utaka, Masanori

  DOI：——

  日期：——
• TSUBOI, SADAO;SAKAMOTO, JUN-ICHI;SAKAI, TAKASHI;UTAKA, MASANORI, CHEM. LETT.,(1989) N, C. 1427-1428
  作者：TSUBOI, SADAO、SAKAMOTO, JUN-ICHI、SAKAI, TAKASHI、UTAKA, MASANORI

  DOI：——

  日期：——