1-phenyl-hexahydro-pyrrolizin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-phenyl-hexahydro-pyrrolizin-3-one
• 英文别名: (1R,8R)-1-phenyl-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: CDNVYJLTWGMPIT-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1-phenyl-hexahydro-pyrrolizin-3-one 、 (1S,7aR)-1-phenyltetrahydro-1H-pyrrolizin-3(2H)-one
  参考文献：
  名称：

  Rhodium-Catalyzed 1,4-Additions to Enantiopure Acceptors: Asymmetric Synthesis of Functionalized Pyrrolizidinones

  摘要：

  The rhodium-catalyzed 1,4-addition of arylboronic acids to an enantiopure heterocyclic acceptor proceeds under ligand control to effect an asymmetric synthesis of functionalized pyrrolizidinones. The protocol allows convenient access to all four stereoisomers of pyrrolizidinone 3a (Ar = Ph) by appropriate selection of substrate and catalyst.

  DOI：

  10.1021/ol900843a

文献信息

• Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions
  作者：Stanisław Leśniak、Ryszard B. Nazarski、Beata Pasternak

  DOI：10.1016/j.tet.2009.06.011

  日期：2009.8

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• Rhodium-Catalyzed 1,4-Additions to Enantiopure Acceptors: Asymmetric Synthesis of Functionalized Pyrrolizidinones
  作者：Ludivine Zoute、Gabriele Kociok-Köhn、Christopher G. Frost

  DOI：10.1021/ol900843a

  日期：2009.6.18

  The rhodium-catalyzed 1,4-addition of arylboronic acids to an enantiopure heterocyclic acceptor proceeds under ligand control to effect an asymmetric synthesis of functionalized pyrrolizidinones. The protocol allows convenient access to all four stereoisomers of pyrrolizidinone 3a (Ar = Ph) by appropriate selection of substrate and catalyst.