[2-(1H-indol-3-yl)ethyl]-(2-iodo-benzylidene)-amine

• 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-(1H-indol-3-yl)ethyl]-(2-iodo-benzylidene)-amine
• 化学式: C₁₇H₁₅IN₂
• 分子量: 374.224
• InChiKey: YUMSCWOHDQSMKT-YBFXNURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.15
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [2-(1H-indol-3-yl)ethyl]-(2-iodo-benzylidene)-amine 在 palladium diacetate 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1
• 作为产物：
  描述：

  色胺 、 2-碘苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到[2-(1H-indol-3-yl)ethyl]-(2-iodo-benzylidene)-amine
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1

文献信息

• Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan、Mark Thornton-Pett、Jin Zhang

  DOI：10.1016/s0040-4020(00)00628-1

  日期：2000.8

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.