trans-trans-1,3-bis(cyanomethyl)-1,2,3,4,6,7,12,12b-octahydro[2,1-a]-β-carboline

• 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: trans-trans-1,3-bis(cyanomethyl)-1,2,3,4,6,7,12,12b-octahydro[2,1-a]-β-carboline
• 英文别名: 2-[(1R,3R,12bS)-1-(cyanomethyl)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl]acetonitrile
• 化学式: C₁₉H₂₀N₄
• 分子量: 304.395
• InChiKey: JEDXTZWYHUSMGS-NJSLBKSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-trans-1,3-bis(cyanomethyl)-1,2,3,4,6,7,12,12b-octahydro[2,1-a]-β-carboline 在 sodium methylate 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以90%的产率得到(2RS,13aRS,13bRS)-2-cyanomethyl-12-oxo-2,3,5,6,12,13,13a,13b-octahydro-1H-[1,7]naphthyridino[7,8,1-lma]-β-carboline
  参考文献：
  名称：

  A synthetic approach to tacamonine. Access to 3-epitacamonine and 14-epitacamonine

  摘要：

  3-Epitacamonine and 14-epitacamonine have been synthesized starting from the dinitrile 3. The synthetic route was designed on the basis of symmetric considerations which emphasized the establishment of the relative configuration in two of the three stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01025-5
• 作为产物：
  描述：

  cis-1,3-bis(cyanomethyl)-4-cyclopentene 在 二甲基硫 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 trans-trans-1,3-bis(cyanomethyl)-1,2,3,4,6,7,12,12b-octahydro[2,1-a]-β-carboline
  参考文献：
  名称：

  A synthetic approach to tacamonine. Access to 3-epitacamonine and 14-epitacamonine

  摘要：

  3-Epitacamonine and 14-epitacamonine have been synthesized starting from the dinitrile 3. The synthetic route was designed on the basis of symmetric considerations which emphasized the establishment of the relative configuration in two of the three stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01025-5

文献信息

• A synthetic approach to tacamonine. Access to 3-epitacamonine and 14-epitacamonine
  作者：Tse-Lok Ho、Chun-Yuan Su

  DOI：10.1016/s0040-4020(00)01025-5

  日期：2001.1

  3-Epitacamonine and 14-epitacamonine have been synthesized starting from the dinitrile 3. The synthetic route was designed on the basis of symmetric considerations which emphasized the establishment of the relative configuration in two of the three stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.