(1R,2S,5R,7S)-6-acetyl-7-methyl-7-phenyl-6-azabicyclo[3.2.1]octane-2-carbonitrile | 365215-84-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,2S,5R,7S)-6-acetyl-7-methyl-7-phenyl-6-azabicyclo[3.2.1]octane-2-carbonitrile
• 英文别名: normorphan (-)-10
• CAS: 365215-84-5
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: LENYQMOIGIWYSD-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1S,2R,5R,7S)-2-chloro-6-(2,2-dichloroacetyl)-7-phenyl-7-methyl-6-azabicyclo[3.2.1]octane-2-carbonitrile 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 生成 (1R,2S,5R,7S)-6-acetyl-7-methyl-7-phenyl-6-azabicyclo[3.2.1]octane-2-carbonitrile 、 (1R,2R,5R,7S)-6-acetyl-7-methyl-7-phenyl-6-azabicyclo[3.2.1]octane-2-carbonitrile
  参考文献：
  名称：

  Unusual rearrangement and dearomatization reactions in Cu(I)-catalyzed atom transfer radical cyclizations from N-(1-phenylethyl)trichloroacetamides

  摘要：

  Atom transfer radical cyclization of N-(alpha-methyl)benzyl substituted trichloroacetamide upon alpha,beta-unsaturated nitriles in compounds 1, using Cud, trispyridylmethylamine (TPMA), and AIBN as a reducing agent, gives morphan derivatives (2 and 3) and the unusual normorphans 4 and 5, as well as the unexpected azaspirodecanes 6. Stereospecific formation of normorphans involves memory of chirality in the cyclization step and azaspirodecanes are generated by a radical dearomative ipsocyclization followed by a radical dimerization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.042