(R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol | 445433-08-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol
• 英文别名: (R)-[(2S,4S,5R)-5-(3-benzyliminopropyl)-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• CAS: 445433-08-9
• 化学式: C₂₇H₃₁N₃O
• 分子量: 413.563
• InChiKey: LADLHNSZHZXXLN-RGXZNCPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到11-N-benzylaminomethyl-10,11-dihydrocinchonidine
  参考文献：
  名称：

  Highly Selective Hydroformylation of the Cinchona Alkaloids

  摘要：

  The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.

  DOI：

  10.1021/jo0255173
• 作为产物：
  描述：

  辛可尼丁 在 acetylacetonatodicarbonylrhodium(l) [(2,4-di-t-Bu-C₆H₃-O)2POCH₂]4C 、 氢气 作用下， 以 甲苯 为溶剂， 90.0 ℃ 、2.0 MPa 条件下， 反应 23.0h， 生成 (R)-((1S,2S,4S,5R)-5-{3-[(Z)-Benzylimino]-propyl}-1-aza-bicyclo[2.2.2]oct-2-yl)-quinolin-4-yl-methanol
  参考文献：
  名称：

  Highly Selective Hydroformylation of the Cinchona Alkaloids

  摘要：

  The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.

  DOI：

  10.1021/jo0255173

文献信息

• Highly Selective Hydroformylation of the Cinchona Alkaloids
  作者：Marielle Lambers、Felix H. Beijer、José M. Padron、Imre Toth、Johannes G. de Vries

  DOI：10.1021/jo0255173

  日期：2002.7.1

  The four naturally occurring cinchona alkaloids were subjected to hydroformylation to create an extra functional group that allows immobilization. Cinchonidine, quinine, and quinidine, could be hydroformylated with virtually complete terminal selectivity, using a rhodium/tetraphosphite catalyst. The cinchonidine aldehyde was reduced to the alcohol and subjected to reductive amination with benzylamine.