2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester | 124929-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester
• CAS: 124929-01-7
• 化学式: C₂₅H₃₇IO₄Se
• 分子量: 607.431
• InChiKey: DLDMZTZBQQONEF-MMCLJHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester 以 二甲基亚砜 为溶剂， 反应 0.25h， 以47%的产率得到(3aR,4R,6aR)-3-methyl-4-octyl-3-phenylselanyl-4,6a-dihydro-3aH-furo[3,4-b]furan-2,6-dione
  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：

  ethyl 3-chloro-4-oxododecanoate 在 盐酸 、 sodium tetrahydroborate 、 碘 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 60.17h， 生成 2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester
  参考文献：
  名称：

  Tsuboi, Sadao; Sakamoto, Jun-ichi; Sakai, Takashi, Chemistry Letters, 1989, p. 1427 - 1428

  摘要：

  DOI：