(1S,5S)-4-(chloromethyl)-2,2-dimethyl-6-methylene-3-azabicyclo[3.3.1]non-3-ene | 1583272-64-3

• 分子结构分类: 有机化合物
• 英文名称: (1S,5S)-4-(chloromethyl)-2,2-dimethyl-6-methylene-3-azabicyclo[3.3.1]non-3-ene
• 英文别名: (1S,5S)-2-(chloromethyl)-4,4-dimethyl-8-methylidene-3-azabicyclo[3.3.1]non-2-ene
• CAS: 1583272-64-3
• 化学式: C₁₂H₁₈ClN
• 分子量: 211.735
• InChiKey: PZWCYPNTGLCGRY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  beta-pinene 、 氯乙腈 在 硫酸 、 水 作用下， 以 苯 为溶剂， 反应 3.0h， 以31%的产率得到2-chloro-N-[(1S,5S,6S)-4-(chloromethyl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non-3-en-6-yl]acetamide
  参考文献：
  名称：

  Formation of 3-azabicyclo[3.3.1]non-3-enes: imino amides vs. imino alkenes

  摘要：

  An effective method for synthesising alkaloidlike compounds containing the 3-azabicyclo[3.3.1]non-3-ene core structure was successfully carried out in a stereo-selective manner via the bridged-Ritter reactions. Important optically active 6-alkyl(aryl)amido-4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]non-3-enes (imino amides) and 4-alkyl(aryl)-2,2,6-trimethyl-3-azabicyclo[3.3.1]nona-3,6-dienes (imino alkenes) were obtained in one step from (-)-beta-pinene and the respective nitriles in the presence of concentrated H2SO4. The relative compositions of these products were controlled by varying the reaction conditions. Kinetic studies were conducted to enable a mechanistic understanding of the reaction pathways.

  DOI：

  10.1007/s00706-014-1185-x