(1R,8S)-1-chloromethyl-3-oxo-hexahydropyrrolizidine | 141521-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1R,8S)-1-chloromethyl-3-oxo-hexahydropyrrolizidine
• 英文别名: (1R,8S)-1-(chloromethyl)-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 141521-14-4
• 化学式: C₈H₁₂ClNO
• 分子量: 173.642
• InChiKey: VCKWRKMDMNUOJZ-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,8S)-1-chloromethyl-3-oxo-hexahydropyrrolizidine 在 sodium iodide 作用下， 以 丁酮 为溶剂， 以81%的产率得到(1R,8S)-1-iodomethyl-3-oxo-hexahydropyrrolizidine
  参考文献：
  名称：

  Synthesis of pyrrolizidines via copper(I) catalyzed radical atom transfer cyclization

  摘要：

  Trachelanthamidine and pseudoheliotridane are synthesized from 2S)-N-trichlkoroacetyl-2-vinylpyrrolidine (5) by a 5-exo-trig radical cyclization. The intermediate radical is generated heating 5 in a sealed tube (CH3CN/ 160-degrees-C) using CuCl as catalyst and the cyclization occurs in very good yield (93%). Cyclized product 6 is transformed either into (-)-trachelanthamidine (55% yield from 5) or into (-)-pseudoheliotridane (42% yield from 5).

  DOI：

  10.1016/s0040-4020(01)88722-6
• 作为产物：
  描述：

  (S)-2-vinylpyrrolidine 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium acetate 、 copper(l) chloride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 (1R,8S)-1-chloromethyl-3-oxo-hexahydropyrrolizidine
  参考文献：
  名称：

  Synthesis of pyrrolizidines via copper(I) catalyzed radical atom transfer cyclization

  摘要：

  Trachelanthamidine and pseudoheliotridane are synthesized from 2S)-N-trichlkoroacetyl-2-vinylpyrrolidine (5) by a 5-exo-trig radical cyclization. The intermediate radical is generated heating 5 in a sealed tube (CH3CN/ 160-degrees-C) using CuCl as catalyst and the cyclization occurs in very good yield (93%). Cyclized product 6 is transformed either into (-)-trachelanthamidine (55% yield from 5) or into (-)-pseudoheliotridane (42% yield from 5).

  DOI：

  10.1016/s0040-4020(01)88722-6