diethyl 2-benzoyl-4-methylene-1-methyl-pyrrolidine-3,3-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 2-benzoyl-4-methylene-1-methyl-pyrrolidine-3,3-dicarboxylate
• 英文别名: Diethyl 2-benzoyl-1-methyl-4-methylidenepyrrolidine-3,3-dicarboxylate
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: ZWHPBAOPLYFZNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰基亚甲基三苯基膦 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 生成 diethyl 2-benzoyl-4-methylene-1-methyl-pyrrolidine-3,3-dicarboxylate
  参考文献：
  名称：

  Zinc- and Indium-Promoted Conjugate Addition−Cyclization Reactions of Ethenetricarboxylates with Propargylamines and Alcohol:  Novel Methylenepyrrolidine and Methylenetetrahydrofuran Syntheses

  摘要：

  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.

  DOI：

  10.1021/jo0602118

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.