dimethyl 4-benzylidene-1-methyl-2-phenyl-pyrrolidine-3,3-dicarboxylate | 500879-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: dimethyl 4-benzylidene-1-methyl-2-phenyl-pyrrolidine-3,3-dicarboxylate
• CAS: 500879-57-2
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: XVOLJDPMINAABH-NBVRZTHBSA-N

物化性质

• 沸点：
  455.6±45.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 4-benzylidene-1-methyl-2-phenyl-pyrrolidine-3,3-dicarboxylate 在 palladium on activated charcoal 氢气 、 乙酸乙酯 作用下， 20.0 ℃ 、506.62 kPa 条件下， 以95%的产率得到dimethyl (+/-)-(2RS,4SR)-4-benzyl-1-methyl-2-phenylpyrrolidine-3,3-dicarboxylate
  参考文献：
  名称：

  Pd-catalyzed one-pot coupling of allylamines, activated alkenes, and unsaturated halides (or triflate): an atom efficient synthesis of highly functionalized pyrrolidines

  摘要：

  A Pd-catalyzed three-component assembling of highly functionalized 4-benzyl-(and allyl-)pyrrolidines was achieved based on a combination of allyl amines, gem-diactivated alkenes, and unsaturated halides (or triflate). (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.07.039
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 碘苯 、 亚苄基丙二酸二甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以65%的产率得到dimethyl 4-benzylidene-1-methyl-2-phenyl-pyrrolidine-3,3-dicarboxylate
  参考文献：
  名称：

  Pd-catalyzed one-pot coupling of allylamines, activated alkenes, and unsaturated halides (or triflate): an atom efficient synthesis of highly functionalized pyrrolidines

  摘要：

  A Pd-catalyzed three-component assembling of highly functionalized 4-benzyl-(and allyl-)pyrrolidines was achieved based on a combination of allyl amines, gem-diactivated alkenes, and unsaturated halides (or triflate). (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.07.039

文献信息

• Three-component one-pot synthesis of functionalised (Z)-4-benzylidene (and alkenylidene) pyrrolidines
  作者：Stéphane Azoulay、Nuno Monteiro、Geneviève Balme

  DOI：10.1016/s0040-4039(02)02383-3

  日期：2002.12

  A three-component synthesis of stereodefined 4-benzylidene-(or alkenylidene)-pyrrolidines from simple, readily available starting materials is described. This one-pot process is initiated by a conjugate addition of a propargylamine to a gem-diactivated olefin subsequently followed by a carbopalladation involving an aryl halide (or vinyl triflate). (C) 2002 Elsevier Science Ltd. All rights reserved.