N,N-dimethyl-5-oxo-4-phenyl-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxamide | 1428156-95-9

• 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: N,N-dimethyl-5-oxo-4-phenyl-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxamide
• 英文别名: N,N,4-trimethyl-5-oxo-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxamide；N,N-dimethyl-5-oxo-4-phenyl-3,6,7,7a-tetrahydro-2H-indole-1-carboxamide
• CAS: 1428156-95-9
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: IBWJKBFCUOTTDG-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-5-oxo-4-phenyl-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxamide 在 palladium 10% on activated carbon 、 环己烯 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以43%的产率得到5-Hydroxy-N,N-dimethyl-4-phenylindoline-1-carboxamide
  参考文献：
  名称：

  Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system

  摘要：

  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.

  DOI：

  10.1016/j.tet.2015.08.052
• 作为产物：
  描述：

  N-(but-3-yn-1-yl)cyclopropylamine 在 copper(l) iodide 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 四(三苯基膦)钯 、 sodium sulfate 、 三乙胺 、 三[3,4-双(三氟甲基)苯基]膦 作用下， 以 苯甲腈 、 N,N-二甲基甲酰胺 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 142.0h， 生成 N,N-dimethyl-5-oxo-4-phenyl-2,3,5,6,7,7a-hexahydro-1H-indole-1-carboxamide
  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

• An <i>endo</i> ‐Directing‐Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes
  作者：Olga O. Sokolova、John F. Bower

  DOI：10.1002/anie.202205007

  日期：2022.8.8

  An endo-directing group strategy enables enantioselective (3+1+2) cycloadditions that are triggered by carbonylative C−C bond activation of cyclopropanes. These processes are rare examples of cycloadditions where C−C bond oxidative addition is enantiodetermining.

  内向导向基团策略能够实现对映选择性 (3+1+2) 环加成反应，该环加成反应由环丙烷的羰基化 C-C 键活化引发。这些过程是环加成的罕见例子，其中 C-C 键氧化加成是对映体决定的。