(R)-3-[(S,E)-1-nitro-4-phenylbut-3-en-2-yl]tetrahydropyran-4-one | 1228821-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-[(S,E)-1-nitro-4-phenylbut-3-en-2-yl]tetrahydropyran-4-one
• 英文别名: (3R)-3-[(E,2S)-1-nitro-4-phenylbut-3-en-2-yl]oxan-4-one
• CAS: 1228821-11-1
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: QEFCQNRWLUAXPE-AFJNRPGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  四氢吡喃酮 、 1-nitro-4-phenylbutadiene 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74%的产率得到(R)-3-[(S,E)-1-nitro-4-phenylbut-3-en-2-yl]tetrahydropyran-4-one
  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

• The highly enantioselective Michael addition of ketones to nitrodienes catalyzed by the efficient organocatalyst system of pyrrolidinyl-thioimidazole and chiral thioureido acid
  作者：Zhao-Bo Li、Shu-Ping Luo、Yi Guo、Ai-Bao Xia、Dan-Qian Xu

  DOI：10.1039/c002197k

  日期：——

  The highly enantioselective Michael addition reaction of ketones to nitrodienes was promoted efficiently by the accessible and fine-tunable organocatalytic system of pyrrolidinyl-thioimidazole and chiral thioureido acid. The corresponding adducts were afforded in good yields with high diastereoselectivities (up to 99 : 1) and excellent enantioselectivities (up to 99% ee).

  可利用的和可精细调节的有机催化体系有效地促进了酮对硝基二烯的高对映选择性迈克尔加成反应。 吡咯烷基-硫代咪唑 和手性 硫脲基酸。相应的加合物以良好的收率提供，具有高的非对映选择性（高达99：1）和优异的对映选择性（高达99％ee）。
• 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.