methyl (1S,3R)-16-cyano-17-ethyl-5,15-diazapentacyclo[13.3.1.01,3.04,12.06,11]nonadeca-4(12),6,8,10,17-pentaene-3-carboxylate | 132019-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (1S,3R)-16-cyano-17-ethyl-5,15-diazapentacyclo[13.3.1.01,3.04,12.06,11]nonadeca-4(12),6,8,10,17-pentaene-3-carboxylate
• CAS: 132019-31-9
• 化学式: C₂₂H₂₃N₃O₂
• 分子量: 361.444
• InChiKey: NPJXICPZUDXHJQ-LFZQMPOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  长春质碱 在 sodium tetrahydroborate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 methyl (1S,3R)-16-cyano-17-ethyl-5,15-diazapentacyclo[13.3.1.01,3.04,12.06,11]nonadeca-4(12),6,8,10,17-pentaene-3-carboxylate
  参考文献：
  名称：

  Oxidative fragmentation of catharanthine by dichlorodicyanoquinone

  摘要：

  Oxidation of catharanthine by DDQ leads to formation of products resulting from fragmentation of the C16-C21 bond as well as C3 and C5 dehydrogenation. Among the products are compounds containing a cyclopropane ring formed by bonding between C14 and C16. Cyclopropane ring formation can be also be observed from the intermediate generated by Potier-Polonovski fragmentation of catharanthine N-oxide.

  DOI：

  10.1021/jo00005a007

文献信息

• Oxidative fragmentation of catharanthine by dichlorodicyanoquinone
  作者：Richard J. Sundberg、Phyllis J. Hunt、Patrice Desos、Kumar G. Gadamasetti

  DOI：10.1021/jo00005a007

  日期：1991.3

  Oxidation of catharanthine by DDQ leads to formation of products resulting from fragmentation of the C16-C21 bond as well as C3 and C5 dehydrogenation. Among the products are compounds containing a cyclopropane ring formed by bonding between C14 and C16. Cyclopropane ring formation can be also be observed from the intermediate generated by Potier-Polonovski fragmentation of catharanthine N-oxide.