(1S,2S,3S)-2-nitro-3-(p-tolyl)cyclopropane-1-carbaldehyde | 1154760-53-8

• 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: (1S,2S,3S)-2-nitro-3-(p-tolyl)cyclopropane-1-carbaldehyde
• 英文别名: (1S,2S,3S)-2-(4-methylphenyl)-3-nitrocyclopropane-1-carbaldehyde
• CAS: 1154760-53-8
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: RSCNILPZFXQQAC-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  p-Methyl-zimtaldehyd 在 甲醇 、 sodium tetrahydroborate 、 sodium acetate 、 戴斯-马丁氧化剂 、 DL-脯氨酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (1S,2S,3S)-2-nitro-3-(p-tolyl)cyclopropane-1-carbaldehyde
  参考文献：
  名称：

  α,β-不饱和醛不对称硝基环丙烷化的人工酶——设计与进化

  摘要：

  描述了通过遗传密码扩展生成具有仲胺残基的人工酶。设计酶经过进化，能够以高转化率催化肉桂醛的不对称硝基环丙烷化反应，并具有优异的非对映选择性和对映选择性。

  DOI：

  10.1002/anie.202401635

文献信息

• Enantioselective conjugate addition of 1-bromonitroalkanes to α,β-unsaturated aldehydes catalyzed by chiral secondary amines
  作者：Jun-min Zhang、Zhi-peng Hu、Li-ting Dong、Yi-ning Xuan、Chun-Liang Lou、Ming Yan

  DOI：10.1016/j.tetasy.2009.01.003

  日期：2009.2

  Highly enantioselective conjugate addition of bromonitromethane to α,β-unsaturated aldehydes catalyzed by chiral secondary amines has been achieved. Diphenylprolinol triethylsilyl ether was found to be the best catalyst for the reaction under MeOH/AcONa system. Various β-aryl acroleins afforded nitrocyclopropanes with excellent enantioselectivities and in good yields; however, the reaction of β-alkyl

  已实现了将溴硝基甲烷高度对映体的共轭加成到手性仲胺催化的α，β-不饱和醛上。发现二苯基脯氨醇三乙基甲硅烷基醚是在MeOH / AcONa体系下反应的最佳催化剂。各种β-芳基丙烯醛可提供具有优异对映选择性和高收率的硝基环丙烷。然而，β-烷基丙烯醛的反应没有提供相应的硝基环丙烷。取代的1-溴硝基甲烷，例如1-溴硝基乙烷和1-苯基-1-溴硝基甲烷，也以优异的对映选择性和改进的非对映选择性应用于反应中。新的方法学对于制备高度取代的手性硝基环丙烷是有效的。
• Organocatalytic conjugate addition of 1-bromonitroalkanes to α,β-unsaturated aldehydes: synthesis of nitrocyclopropanes
  作者：Jun-min Zhang、Zhi-peng Hu、Shuang-qi Zhao、Ming Yan

  DOI：10.1016/j.tet.2008.11.060

  日期：2009.1

  A variety of secondary amines were studied as the catalyst in the conjugate addition of 1-bromonitromethane to alpha,beta-unsaturated aldehydes. Proline was identified as the best catalyst for this reaction. MeOH/AcONa system was found to provide much better yields than CHCl3/Et3N system reported before. Good yields of nitrocyclopropane products were obtained with a variety of beta-aryl acroleins. Several substituted 1-bromonitrornethanes were also examined in the reaction. Both 1-bromonitroethane and 1-phenyl-1-bromonitromethane gave the corresponding nitrocyclopropanes in good yields. The diastereo-selectivity of the reaction was strongly affected by the steric hindrance of 1-bromonitroalkanes. (C) 2008 Elsevier Ltd. All rights reserved.
• An Artificial Enzyme for Asymmetric Nitrocyclopropanation of α,β‐Unsaturated Aldehydes ‐ Design and Evolution
  作者：Ming-Zhu Yu、Ye Yuan、Zhen-Jie Li、Thittaya Kunthic、He-Xiang Wang、Chen Xu、Zheng Xiang

  DOI：10.1002/anie.202401635

  日期：——

  Generation of an artificial enzyme that features a secondary amine residue by genetic code expansion is described. The designer enzyme was evolved to catalyze the asymmetric nitrocyclopropanation of cinnamaldehydes at high conversions with excellent diastereo- and enantioselectivity.

  描述了通过遗传密码扩展生成具有仲胺残基的人工酶。设计酶经过进化，能够以高转化率催化肉桂醛的不对称硝基环丙烷化反应，并具有优异的非对映选择性和对映选择性。