(5R,9S)-5-hexylindolizidine

• 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: (5R,9S)-5-hexylindolizidine
• 英文别名: (5R,8aS)-5-hexyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• 化学式: C₁₄H₂₇N
• 分子量: 209.375
• InChiKey: AXAQOPLJIFRMGI-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2S-(4S))-N-(2,2,2-trichloroethoxycarbonyl)-2-(4-hydroxydecyl)pyrrolidine 在 吡啶 、 4-二甲氨基吡啶 、 10% Cd/Pd 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (5R,9S)-5-hexylindolizidine
  参考文献：
  名称：

  New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor

  摘要：

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00338-3

文献信息

• Enantioselective Synthesis of Indolizidine Alkaloid <i>trans</i>-209D
  作者：Carlos Alegret、Antoni Riera

  DOI：10.1021/jo801645p

  日期：2008.11.7

  (S)-N-Boc-baikiain, readily accessible from enantiomerically enriched 2,3-epoxy-5-hexen-1-ol 4 (prepared by Sharpless asymmetric epoxidation), was used as the starting material in the synthesis of indolizidine alkaloid trans-209D , which was obtained in 13 steps and 14% yield from 1 (5% from 4).

  （S）-N-Boc-baikiain可从对映异构体富集的2,3-环氧--5-己烯-1-醇4（由Sharpless不对称环氧化制备）中用作合成吲哚并立生物碱的起始原料-209D，以13个步骤得到，从1（14的产率为4）的产率为14％。
• New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor
  作者：Hiroki Takahata、Minoru Kubota、Kozue Ihara、Naoki Okamoto、Takefumi Momose、Nehad Azer、Amira T. Eldefrawi、Mohyee E. Eldefrawi

  DOI：10.1016/s0957-4166(98)00338-3

  日期：1998.9

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.