(4R,5R)-5-(2,4-dimethoxyphenyl)-4-methyl-3-methylidenepyrrolidin-2-one | 1256350-33-0

• 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: (4R,5R)-5-(2,4-dimethoxyphenyl)-4-methyl-3-methylidenepyrrolidin-2-one
• CAS: 1256350-33-0
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: RSKVZOMVFSBGIQ-AMIZOPFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (E)-2-(bromomethyl)but-2-enoate 、 (R)-N-(2,4-dimethoxybenzylidene)-2-methylpropane-2-sulfinamide 在 lithium chloride 、 锌 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 1,4-二氧六环 为溶剂， 反应 8.5h， 以78%的产率得到(4R,5R)-5-(2,4-dimethoxyphenyl)-4-methyl-3-methylidenepyrrolidin-2-one
  参考文献：
  名称：

  One-Pot Synthesis of Chiral α-Methylene-γ-lactams with Excellent Diastereoselectivities and Enantioselectivities

  摘要：

  An efficient one-pot asymmetric synthesis of highly substituted gamma-lactams containing a-methylene groups has been successfully developed. A wide range of gamma-lactams could be obtained in high yields with excellent diastereomeric ratios of up to 99:1 in favor of trans isomers. In particular, excellent enantioselectivities of the two newly formed stereogenic centers with up to 99% ee were observed.

  DOI：

  10.1021/ol102148b

文献信息

• One-Pot Synthesis of Chiral α-Methylene-γ-lactams with Excellent Diastereoselectivities and Enantioselectivities
  作者：An Shen、Min Liu、Zhen-Shan Jia、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/ol102148b

  日期：2010.11.19

  An efficient one-pot asymmetric synthesis of highly substituted gamma-lactams containing a-methylene groups has been successfully developed. A wide range of gamma-lactams could be obtained in high yields with excellent diastereomeric ratios of up to 99:1 in favor of trans isomers. In particular, excellent enantioselectivities of the two newly formed stereogenic centers with up to 99% ee were observed.