(6S,7S,8S,8aS)-6-(2-bromoethyl)-3-oxooctahydroindolizine-7,8-diyl diacetate | 1233086-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (6S,7S,8S,8aS)-6-(2-bromoethyl)-3-oxooctahydroindolizine-7,8-diyl diacetate
• CAS: 1233086-92-4
• 化学式: C₁₄H₂₀BrNO₅
• 分子量: 362.221
• InChiKey: HCFKGPOPKLJJEW-IMIFBBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (6S,7S,8S,8aS)-6-(2-bromoethyl)-3-oxooctahydroindolizine-7,8-diyl diacetate 在 氢气 、 三乙胺 作用下， 60.0 ℃ 、800.01 kPa 条件下， 反应 22.0h， 以70%的产率得到(6S,7S,8S,8aS)-6-ethyl-3-oxooctahydroindolizine-7,8-diyl diacetate
  参考文献：
  名称：

  Regioselective ring opening of the chiral non-racemic furoindolizidinols. New entry to alkylindolizidinediol derivatives

  摘要：

  New homochiral 6-ethyl-7,8-indolizidinediol derivatives, related to the bioactive dihydroxylated indolizidine alkaloids, are reported to be easily accessible in four or five steps from enantiopure 9-hydroxy-octahydrofuro[3,2-f]indolizin-6(2H)-ones in good overall yields and high diastereomeric purities. The simple procedure used herein involves a regiospecific THF-ring opening as a key step, in addition to the C-Br linkage reduction, and the alcohol deprotection followed by lactam reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.018
• 作为产物：
  描述：

  (3aS,8aS,9S,9aS)-9-hydroxyoctahydrofuro[3,2-f]indolizin-6(2H)-one 、 乙酰溴 在 锌 作用下， 以 二氯甲烷 为溶剂， 反应 25.75h， 以81%的产率得到(6S,7S,8S,8aS)-6-(2-bromoethyl)-3-oxooctahydroindolizine-7,8-diyl diacetate
  参考文献：
  名称：

  Regioselective ring opening of the chiral non-racemic furoindolizidinols. New entry to alkylindolizidinediol derivatives

  摘要：

  New homochiral 6-ethyl-7,8-indolizidinediol derivatives, related to the bioactive dihydroxylated indolizidine alkaloids, are reported to be easily accessible in four or five steps from enantiopure 9-hydroxy-octahydrofuro[3,2-f]indolizin-6(2H)-ones in good overall yields and high diastereomeric purities. The simple procedure used herein involves a regiospecific THF-ring opening as a key step, in addition to the C-Br linkage reduction, and the alcohol deprotection followed by lactam reduction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.018