2,2,2-Trichloro-N-[2-(1H-indol-3-yl)-ethyl]-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide | 730961-18-9

• 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: 2,2,2-Trichloro-N-[2-(1H-indol-3-yl)-ethyl]-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide
• 英文别名: 2,2,2-trichloro-N-[2-(1H-indol-3-yl)ethyl]-N-[(4-oxocyclohex-2-en-1-yl)methyl]acetamide
• CAS: 730961-18-9
• 化学式: C₁₉H₁₉Cl₃N₂O₂
• 分子量: 413.731
• InChiKey: AJFCQSSYVZELFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-N-[2-(1H-indol-3-yl)-ethyl]-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以60%的产率得到(4aR,8aR)-2-[2-(1H-Indol-3-yl)-ethyl]-hexahydro-isoquinoline-3,6-dione
  参考文献：
  名称：

  Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis -perhydroisoquinoline-3,6-diones

  摘要：

  Intramolecular reactions between 1-(carbamoyl)dichloromethyl radicals and enones acting as radical acceptors are reported for the first time. The Bu3SnH promoted 6-exo reaction of trichloroacetamides with enones, avoiding the 1,5-hydrogen transfer, constitutes a new synthetic entry to cis-perhydoisoquinoline-3,6-diones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.104
• 作为产物：
  描述：

  (1,4-Dioxa-spiro[4.5]dec-8-ylmethyl)-[2-(1H-indol-3-yl)-ethyl]-amine 在 盐酸 、 碘代三甲硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2,2,2-Trichloro-N-[2-(1H-indol-3-yl)-ethyl]-N-(4-oxo-cyclohex-2-enylmethyl)-acetamide
  参考文献：
  名称：

  Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis -perhydroisoquinoline-3,6-diones

  摘要：

  Intramolecular reactions between 1-(carbamoyl)dichloromethyl radicals and enones acting as radical acceptors are reported for the first time. The Bu3SnH promoted 6-exo reaction of trichloroacetamides with enones, avoiding the 1,5-hydrogen transfer, constitutes a new synthetic entry to cis-perhydoisoquinoline-3,6-diones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.104

文献信息

• Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis -perhydroisoquinoline-3,6-diones
  作者：Xavier Vila、Josefina Quirante、Laura Paloma、Josep Bonjoch

  DOI：10.1016/j.tetlet.2004.04.104

  日期：2004.6

  Intramolecular reactions between 1-(carbamoyl)dichloromethyl radicals and enones acting as radical acceptors are reported for the first time. The Bu3SnH promoted 6-exo reaction of trichloroacetamides with enones, avoiding the 1,5-hydrogen transfer, constitutes a new synthetic entry to cis-perhydoisoquinoline-3,6-diones. (C) 2004 Elsevier Ltd. All rights reserved.