5-(furan-2-yl)-3-methylene-4-phenyl-1-tosylpyrrolidin-2-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: 5-(furan-2-yl)-3-methylene-4-phenyl-1-tosylpyrrolidin-2-one
• 英文别名: (4R,5S)-5-(furan-2-yl)-3-methylidene-1-(4-methylphenyl)sulfonyl-4-phenylpyrrolidin-2-one
• 化学式: C₂₂H₁₉NO₄S
• 分子量: 393.463
• InChiKey: XXQLQEWLRWFRPX-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(bromomethyl)-3-phenylacrylate 、 2-furaldehyde tosylimine 在 1,2-二碘乙烷 、 锌 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以81%的产率得到5-(furan-2-yl)-3-methylene-4-phenyl-1-tosylpyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of cis-3,4-diaryl α-methylene-γ-butyrolactams via sonochemical Barbier-type reaction

  摘要：

  A series of cis-3,4-diaryl alpha-methylene-gamma-butyrolactams were synthesized by the addition reaction of 3-phenylallyl bromide with N-tosyl aldimine via sonochemical Barbier-type reaction condition and then followed by the in situ intramolecular amidation. The cis-3,4-diaryl alpha-methylene-gamma-butyrolactam was obtained as the sole regio- and stereoisomeric product when N-tosyl aldimine was used as the substrate whereas the monoaryl alpha-methylene-gamma-butyrolactam was also generated when N-phenyl aldimine was used. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.057

文献信息

• Synthesis of cis-3,4-diaryl α-methylene-γ-butyrolactams via sonochemical Barbier-type reaction
  作者：Adam Shih-Yuan Lee、Yu-Ting Chang

  DOI：10.1016/j.tetlet.2010.05.057

  日期：2010.7

  A series of cis-3,4-diaryl alpha-methylene-gamma-butyrolactams were synthesized by the addition reaction of 3-phenylallyl bromide with N-tosyl aldimine via sonochemical Barbier-type reaction condition and then followed by the in situ intramolecular amidation. The cis-3,4-diaryl alpha-methylene-gamma-butyrolactam was obtained as the sole regio- and stereoisomeric product when N-tosyl aldimine was used as the substrate whereas the monoaryl alpha-methylene-gamma-butyrolactam was also generated when N-phenyl aldimine was used. (C) 2010 Elsevier Ltd. All rights reserved.