13b-(trifluoromethyl)-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one | 1598385-65-9

• 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: 13b-(trifluoromethyl)-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
• 英文别名: 2-(Trifluoromethyl)-10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3,5,7,14,16,18-heptaen-9-one；2-(trifluoromethyl)-10,20-diazapentacyclo[11.7.0.02,10.03,8.014,19]icosa-1(13),3,5,7,14,16,18-heptaen-9-one
• CAS: 1598385-65-9
• 化学式: C₁₉H₁₃F₃N₂O
• 分子量: 342.32
• InChiKey: WVWXWSQMAFYBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2-(1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮 在 甲烷磺酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 13b-(trifluoromethyl)-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
  参考文献：
  名称：

  One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives

  摘要：

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.

  DOI：

  10.1021/jo5002998

文献信息

• One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives
  作者：Vinay Kumar Pandey、Pazhamalai Anbarasan

  DOI：10.1021/jo5002998

  日期：2014.5.2

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.