(S)-8-hydroxyhexahydroindolizin-5(1H)-one | 1407965-71-2

• 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: (S)-8-hydroxyhexahydroindolizin-5(1H)-one
• 英文别名: (8aS)-8-hydroxy-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 1407965-71-2
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ZFWFXXUMCVXKSR-PKPIPKONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-8-hydroxyhexahydroindolizin-5(1H)-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到(8aS)-六氢-5,8-吲嗪二酮
  参考文献：
  名称：

  Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

  摘要：

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.061
• 作为产物：
  描述：

  (2S)-benzyl 2-((E)-1-hydroxy-4-methoxy-4-oxobut-2-enyl)pyrrolidine-1-carboxylate 在 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到(S)-8-hydroxyhexahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

  摘要：

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.061

文献信息

• Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D
  作者：Prakash R. Sultane、Amar R. Mohite、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2012.08.061

  日期：2012.10

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.