(S)-2-((R,E)-3-methyl-1-nitro-4-phenylbut-3-en-2-yl)cyclohexanone | 1400268-22-5

• 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: (S)-2-((R,E)-3-methyl-1-nitro-4-phenylbut-3-en-2-yl)cyclohexanone
• 英文别名: (2S)-2-[(E,2R)-3-methyl-1-nitro-4-phenylbut-3-en-2-yl]cyclohexan-1-one
• CAS: 1400268-22-5
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: GJGWLORRVAFLBF-QJLHHFGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-methyl-4-nitrobuta-1,3-dienyl)benzene 、 环己酮 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80%的产率得到(S)-2-((R,E)-3-methyl-1-nitro-4-phenylbut-3-en-2-yl)cyclohexanone
  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

• 4-Fluoro and 4-Hydroxy Pyrrolidine-thioxotetrahydropyrimidinones: Organocatalysts for Green Asymmetric Transformations in Brine
  作者：Nikolaos Kaplaneris、Giorgos Koutoulogenis、Marianna Raftopoulou、Christoforos G. Kokotos

  DOI：10.1021/acs.joc.5b00283

  日期：2015.6.5

  The synthesis of both trans- and cis-diastereomers of pyrrolidinine-thioxotetrahydropyrimidinone bearing either a fluorine or a hydroxyl group was accomplished. The new compounds were tested for their catalytic properties in a variety of asymmetric organic transformations and compared with the first generation catalyst. It was found that the new catalysts could efficiently catalyze the reactions in

  两者的合成反式-和顺pyrrolidinine-thioxotetrahydropyrimidinone轴承任一个氟或羟基的-diastereomers被完成。测试了这些新化合物在各种不对称有机转化中的催化性能，并与第一代催化剂进行了比较。已经发现，新型催化剂可以在不使用有机溶剂的情况下，并且通过使用几乎化学计量的试剂，可以有效地催化盐水中的反应。因此，通过简单的提取就可以分离出产物，从而避免了以极高的收率，非对映选择性和对映选择性使用色谱法。
• Prolinethiol Ether Catalysis in an Asymmetric Michael Reaction: Solvent-Free Synthesis of Functionalized Monohaloalkenes
  作者：Ai-Bao Xia、Chao Wu、Dan-Qian Xu、Yi-Feng Wang、Xiao-Hua Du、Zhao-Bo Li、Zhen-Yuan Xu

  DOI：10.1021/jo302288z

  日期：2013.2.1

  The organocatalytic Michael reaction of ketones with γ-monohalonitrodienes catalyzed by chiral prolinethiol ether under solvent-free conditions was developed. The described method represents a novel approach for accessing highly functionalized monohaloalkenes with α, β-stereocenters of up to >99% ee.

  研究了手性脯硫醇醚在无溶剂条件下，酮与γ-单卤代硝基二烯的有机迈克尔反应。所描述的方法代表了一种新颖的方法，用于获得具有高达> 99％ee的α，β-立体中心的高度官能化的单卤代烯烃。