1-phenyl-2-(N-benzyloxycarbony-5-chlorolindolin-2-yl)ethanone | 1447138-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(N-benzyloxycarbony-5-chlorolindolin-2-yl)ethanone
• 英文别名: benzyl (2R)-5-chloro-2-phenacyl-2,3-dihydroindole-1-carboxylate
• CAS: 1447138-20-6
• 化学式: C₂₄H₂₀ClNO₃
• 分子量: 405.881
• InChiKey: MPUWOLPRYJUSTA-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-N-2-丙烯-1-基-苯胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 N-[3,5-双(三氟甲基)苯基]-N'-[(9R)-6'-甲氧基辛可宁-9-基]脲 、 三氟化硼乙醚 、 四丁基溴化铵 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 均三甲苯 为溶剂， 反应 64.0h， 生成 1-phenyl-2-(N-benzyloxycarbony-5-chlorolindolin-2-yl)ethanone 、 1-phenyl-2-(N-benzyloxycarbony-5-chlorolindolin-2-yl)ethanone
  参考文献：
  名称：

  Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts

  摘要：

  A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The catalytic process was shown to be highly versatile and applicable to a wide range of substrates due to the flexible catalytic mechanism utilizing a noncovalent interaction.

  DOI：

  10.1021/ol401538b

文献信息

• Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts
  作者：Ryota Miyaji、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol401538b

  日期：2013.7.19

  A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The catalytic process was shown to be highly versatile and applicable to a wide range of substrates due to the flexible catalytic mechanism utilizing a noncovalent interaction.