diethyl 1-methyl-4-methylene-2-phenylpyrrolidine-3,3-tricarboxylate

• 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: diethyl 1-methyl-4-methylene-2-phenylpyrrolidine-3,3-tricarboxylate
• 英文别名: Diethyl 1-methyl-4-methylidene-2-phenylpyrrolidine-3,3-dicarboxylate
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: USRHACRUHIARPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基炔丙基胺 、 亚苯甲基丙二酸二乙酯 在 copper(l) iodide 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到diethyl 1-methyl-4-methylene-2-phenylpyrrolidine-3,3-tricarboxylate
  参考文献：
  名称：

  A one pot synthesis of various pyrrolidines via a tandem Michael addition-transition metal-catalysed cyclisation reaction

  摘要：

  A variety of substituted 3-methylene pyrrolidines may be obtained by reaction of propargyl amines with Michael accepters in a single step catalysed by copper(I). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02631-8

文献信息

• Zinc- and Indium-Promoted Conjugate Addition−Cyclization Reactions of Ethenetricarboxylates with Propargylamines and Alcohol:  Novel Methylenepyrrolidine and Methylenetetrahydrofuran Syntheses
  作者：Satoshi Morikawa、Shoko Yamazaki、Yoshiteru Furusaki、Naoya Amano、Kazumi Zenke、Kiyomi Kakiuchi

  DOI：10.1021/jo0602118

  日期：2006.4.1

  A new zinc- and indium-promoted conjugate addition-cyclization reaction to afford nitrogen- and oxygen-containing five-membered heterocycles has been developed. Reaction of ethenetricarboxylates with propargylamines (1 equiv) in the presence of ZnBr2 or InBr3 afforded methylenepyrrolidines in high yields. The stoichiometric use of ZnBr2 or InBr3 at room temperature and the catalytic use of lnBr(3)(-) Et3N at 80 degrees C were effective. Reaction of ethenetricarboxylates with propargyl alcohol in the presence of ZnBr2, or InBr3 afforded methylenetetrahydrofurans.
• A one pot synthesis of various pyrrolidines via a tandem Michael addition-transition metal-catalysed cyclisation reaction
  作者：Blandine Clique、Nuno Monteiro、Geneviève Balme

  DOI：10.1016/s0040-4039(98)02631-8

  日期：1999.2

  A variety of substituted 3-methylene pyrrolidines may be obtained by reaction of propargyl amines with Michael accepters in a single step catalysed by copper(I). (C) 1999 Elsevier Science Ltd. All rights reserved.