(S)-benzyl 2-(1-hydroxyallyl)pyrrolidine-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-benzyl 2-(1-hydroxyallyl)pyrrolidine-1-carboxylate
• 英文别名: benzyl (2S)-2-(1-hydroxyprop-2-enyl)pyrrolidine-1-carboxylate
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: CYSFDBUXVHPFTK-LSLKUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

   (S)-benzyl 2-(1-hydroxyallyl)pyrrolidine-1-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四氧化锇 、 5%-palladium/activated carbon 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 10.0h， 生成 (6S,7R,8R,8aS)-6,7,8-trihydroxy-hexahydro-1H-indolizin-5-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
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-proline-N'-methoxy-N'-methylamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成  (S)-benzyl 2-(1-hydroxyallyl)pyrrolidine-1-carboxylate
  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.