(S)-2-[(S,E)-4-(4-methoxyphenyl)-1-nitrobut-3-en-2-yl]cyclopentanone | 1228821-18-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-[(S,E)-4-(4-methoxyphenyl)-1-nitrobut-3-en-2-yl]cyclopentanone
• 英文别名: (2S)-2-[(E,2S)-4-(4-methoxyphenyl)-1-nitrobut-3-en-2-yl]cyclopentan-1-one
• CAS: 1228821-18-8
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: NISIDZIOJZDCGP-JGOVJGDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-Nitro-1-(4-methoxy-phenyl)-butadien-(1,3) 、 环戊酮 在 (S)-6-phenyl-3-[(S)-pyrrolidin-2-ylmethyl]-2-thioxotetrahydropyrimidin-4(1H)-one 、 水 、 对硝基苯甲酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以83%的产率得到(S)-2-[(S,E)-4-(4-methoxyphenyl)-1-nitrobut-3-en-2-yl]cyclopentanone
  参考文献：
  名称：

  Pyrrolidine-thioxotetrahydropyrimidinone as an efficient organocatalyst for the enantioselective Michael addition of cyclic ketones to nitrodienes

  摘要：

  Among the various Michael additions, the enantioselective reaction between cyclic ketones and nitrodienes has received little attention in comparison to the corresponding reaction with nitroolefins. A bifunctional organocatalyst consisting of the pyrrolidine moiety and a thioxotetrahydropyrimidinone ring successfully catalyzed this asymmetric transformation. The products of the reaction between various ketones and nitrodienes were obtained in high yields (up to 96%) with excellent diastereo- (up to >98:2 dr) and enantioselectivities (up to 99:1% er). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.078

文献信息

• Pyrrolidine-thioxotetrahydropyrimidinone as an efficient organocatalyst for the enantioselective Michael addition of cyclic ketones to nitrodienes
  作者：Michail Tsakos、Maria Trifonidou、Christoforos G. Kokotos

  DOI：10.1016/j.tet.2012.07.078

  日期：2012.10

  Among the various Michael additions, the enantioselective reaction between cyclic ketones and nitrodienes has received little attention in comparison to the corresponding reaction with nitroolefins. A bifunctional organocatalyst consisting of the pyrrolidine moiety and a thioxotetrahydropyrimidinone ring successfully catalyzed this asymmetric transformation. The products of the reaction between various ketones and nitrodienes were obtained in high yields (up to 96%) with excellent diastereo- (up to >98:2 dr) and enantioselectivities (up to 99:1% er). (C) 2012 Elsevier Ltd. All rights reserved.