1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole | 847653-05-8

• 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: 1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole
• 英文别名: Tert-butyl 3-(cyclopentylidenemethyl)indole-1-carboxylate
• CAS: 847653-05-8
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: ZJDDWMOYSCFJLO-UHFFFAOYSA-N

物化性质

• 沸点：
  436.7±38.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到13-cyclopentyl-6,7,12,13-tetrahydrospiro[5H-cyclohepta[1,2-b:4,5-b']diindole-6,1'-cyclopentane]
  参考文献：
  名称：

  Novel cyclo-dimerization of 1-tert-butoxycarbonyl-3-alkenylindole derivatives

  摘要：

  Reaction of 1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole with an excess of trifluoroacetic acid in dichloromethane at room temperature gave a cyclic dimer, 13-cyclopentyl-6,7,12,13-tetrahydrospiro[5H-cyclohepta[1,2-b:4,5-b(1)]di-indole-6,1'-cyclopentane] in 73% yield as the sole product through a novel cyclo-dimerization process. Structure of the cyclic dimer derived from 5-bromo-1-t-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole was elucidated by X-ray crystallographic analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.072
• 作为产物：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 、 溴代三苯基膦环戊酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole
  参考文献：
  名称：

  Novel cyclo-dimerization of 1-tert-butoxycarbonyl-3-alkenylindole derivatives

  摘要：

  Reaction of 1-tert-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole with an excess of trifluoroacetic acid in dichloromethane at room temperature gave a cyclic dimer, 13-cyclopentyl-6,7,12,13-tetrahydrospiro[5H-cyclohepta[1,2-b:4,5-b(1)]di-indole-6,1'-cyclopentane] in 73% yield as the sole product through a novel cyclo-dimerization process. Structure of the cyclic dimer derived from 5-bromo-1-t-butoxycarbonyl-3-cyclopentylidenemethyl-1H-indole was elucidated by X-ray crystallographic analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.072