1-benzoyl-4-methyl-2,3,7,7a-tetrahydro-1H-indol-5(6H)-one | 1428156-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzoyl-4-methyl-2,3,7,7a-tetrahydro-1H-indol-5(6H)-one
• 英文别名: 1-benzoyl-4-methyl-3,6,7,7a-tetrahydro-2H-indol-5-one
• CAS: 1428156-83-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: VXUNZKRVSBUZGT-UHFFFAOYSA-N

物化性质

• 沸点：
  446.6±44.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-戊炔-1-醇 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 二氯甲烷 、 邻二氯苯 、 乙腈 为溶剂， 160.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 1-benzoyl-4-methyl-2,3,7,7a-tetrahydro-1H-indol-5(6H)-one
  参考文献：
  名称：

  Directing Group Enhanced Carbonylative Ring Expansions of Amino-Substituted Cyclopropanes: Rhodium-Catalyzed Multicomponent Synthesis of N-Heterobicyclic Enones

  摘要：

  Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

  DOI：

  10.1021/ja401936c

文献信息

• Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system
  作者：Megan H. Shaw、William G. Whittingham、John F. Bower

  DOI：10.1016/j.tet.2015.08.052

  日期：2016.6

  Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C-C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that accesses N-heterobicyclic enones. Stoichiometric studies on a series of model rhodacyclopentanone complexes outline key structural features and provide a rationale for the efficacy of urea directing groups. A comprehensive evaluation of cycloaddition scope and a 'second generation' cationic Rh(I)-system, which provides enhanced yields and reaction rates for challenging substrates, are presented. (C) 2015 The Authors. Published by Elsevier Ltd.