N-benzyl-1-cinnamoylcyclopropanecarboxamide | 1350743-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-benzyl-1-cinnamoylcyclopropanecarboxamide
• CAS: 1350743-43-9
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: OSHZEMRLDLNJHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-cinnamoylcyclopropanecarboxamide 、 苯胺 以 乙醇 为溶剂， 反应 60.0h， 以60%的产率得到5-benzyl-1,6-diphenyl-1,2,3,5,6,7-hexahydro-4H-pyrrolo[3,2-c]pyridin-4-one
  参考文献：
  名称：

  Catalyst-Free Domino Reaction of 1-Acryloyl-1-N-arylcarbamylcyclopropanes with Amines: One-Pot Approach to 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones

  摘要：

  AbstractA facile one‐pot, catalyst‐free reaction has been developed for the synthesis of 2,3,6,7‐tetrahydro‐1H‐pyrrolo[3,2‐c]pyridin‐4(5H)‐ones from readily available 1‐acryloyl‐1‐N‐arylcarbamylcyclopropanes and amines using a domino ring‐opening/cyclization/aza‐addition sequence. magnified image

  DOI：

  10.1002/adsc.201500251
• 作为产物：
  描述：

  1-乙酰基-N-(苯基甲基)-环丙烷甲酰胺 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以89%的产率得到N-benzyl-1-cinnamoylcyclopropanecarboxamide
  参考文献：
  名称：

  Domino reaction of arylaldehydes and 1-acetylcyclopropanecarboxamides: one-pot access to highly functionalized spiropiperidine-2,4-diones

  摘要：

  A domino reaction based on arylaldehydes and 1-acetylcyclopropanecarboxamides has been developed, which allows one-pot and efficient synthesis of structurally complex piperidine-2,4-diones with multiple functionalities under mild conditions. The overall transformation involves tandem aldol/intramolecular aza-Michael/(aldol)/Michael sequences. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.133

文献信息

• Base-catalyzed bicyclization of dialkyl glutaconates with cinnamoylacetamides: a synthetic strategy for isoquinolinedione derivatives
  作者：Lei Li、Yu-Long Zhao、He Wang、Yi-Jin Li、Xianxiu Xu、Qun Liu

  DOI：10.1039/c3cc46931j

  日期：——

  We report here that polysubstituted dihydroisoquinolones and isoquinolones can be constructed by the one-pot reaction of the readily available acyclic alpha,beta-unsaturated carbonyl precursors and dialkyl glutaconates under mild basic conditions (1-45 min for the former vs. 1-6 h for the latter) via the domino process involving [3+3] annulation/intramolecular aza-cyclization.

  我们在这里报告说，多取代的二氢异喹啉酮和异喹啉酮可以通过在温和的碱性条件下（易燃的前者为1-45分钟，而1-6小时为一小时的无环α，β-不饱和羰基前体和戊二酸二烷基酯的一锅反应）来构建。 （对于后者））通过涉及[3 + 3]环空/分子内氮杂环化的多米诺骨工艺。