(R)-1-(4-bromophenyl)-4-nitro-3-phenylbutan-1-one | 1217435-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-1-(4-bromophenyl)-4-nitro-3-phenylbutan-1-one
• 英文别名: (3R)-1-(4-bromophenyl)-4-nitro-3-phenylbutan-1-one
• CAS: 1217435-90-9
• 化学式: C₁₆H₁₄BrNO₃
• 分子量: 348.196
• InChiKey: VBNKXDGEKIJTLR-AWEZNQCLSA-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  硝基甲烷 、 4-溴查尔酮 在 3-[[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（8α，9S）-6''-甲氧基七氢呋喃-9-基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 60.0h， 以98%的产率得到(R)-1-(4-bromophenyl)-4-nitro-3-phenylbutan-1-one
  参考文献：
  名称：

  使用手性方酸酰胺作为氢键键合有机催化剂，将硝基烷烃高度对映体选择性加成至烷烃。

  摘要：

  容易地合成了一系列基于方酰胺的有机催化剂，并将其用作氢键键合的有机催化剂，用于将硝基烷烃向查尔酮进行对映选择性迈克尔加成反应。这些有机催化剂促进迈克尔加成与高温下低的催化剂负载量（80℃），得到所期望的- [R或小号以高收率和优异的对映选择性（93-96％ee）的由有机催化剂的合适的选择灵活的产品的对映体。

  DOI：

  10.1021/ol102294g

文献信息

• Asymmetric Michael Addition of Aromatic Ketones to Nitroolefins Catalyzed by Simple Chiral Bifunctional Primary Amine-Thioureas
  作者：Liangliang Wang、Xiaoying Xu、Jun Huang、Lin Peng、Qingchun Huang、Lixin Wang

  DOI：10.2174/157017810791514652

  日期：2010.7.1

  Simple chiral primary amine-thiourea catalysts derived from chiral 1,2-diphenylethylenediamine were found to catalyze direct Michael addition of aromatic ketones to nitroolefins with good enantioselectives (up to 86% ee) and excellent yields (up to 97%) for a broad range of substrates and successfully used in the preparation of (R)-Balcofen.

  简单的手性一级胺-硫脲催化剂来源于手性1,2-二苯乙烯二胺，已被发现能够以良好的手性选择性（最高可达86% ee）和优异的产率（最高可达97%）催化芳香酮与硝基烯烃的直接迈克尔加成，适用于广泛的底物，并成功用于(R)-Balcofen的制备。
• Enantioselective Michael Addition of Aromatic Ketones to Nitroolefins Catalyzed by Bifunctional Thioureas and Mechanistic Insight
  作者：Bai-Lin Li、Yi-Feng Wang、Shu-Ping Luo、Ai-Guo Zhong、Zhao-Bo Li、Xiao-Hua Du、Dan-Qian Xu

  DOI：10.1002/ejoc.200900932

  日期：2010.2

  A highly enantioselective Michael reaction of aromatic ketones with nitroolefins was accomplished in the presence of a chiral bifunctional primary amine―thiourea catalyst and 4-nitrobenzoic acid as the co-catalyst; the corresponding adducts were obtained in excellent enantioselectivities (up to 99 % ee) and yields (up to 98 %). The catalytic mechanism of the Michael reaction was confirmed through the

  在手性双官能伯胺-硫脲催化剂和4-硝基苯甲酸作为助催化剂存在下，芳香酮与硝基烯烃的高度对映选择性迈克尔反应；以优异的对映选择性（高达 99 % ee）和产率（高达 98 %）获得了相应的加合物。迈克尔反应的催化机理通过对反应中间体的 ESI-MS 检测和硫脲和硝基烯烃之间氢键的 1 H NMR 检测得到证实。DFT 计算表明，硫脲的手性部分显着影响了加合物的产率和对映选择性，这与观察到的实验结果相对应。
• The Catalytic Efficiency of Isosteviol Derived Bifunctional Primary Amine-Squaramide on Michael Additions of Acetophenone to Nitroalkenes
  作者：Yu-Xia Liu、Zhi-Wei Ma、Chuan-Chuan Wang、Qian Li、Wen-Peng Mai

  DOI：10.2174/1570178619666220112124054

  日期：2022.8

  The isosteviol derived bifunctional primary amine-squaramide organocatalysts were applied in the Michael addition between nitroalkenes and acetophenone. The conjugate addition isomers of two configurations were observed with high yields (up to 93% yield) and good enantioselectivity (up to 91% ee) at room temperature.

  摘要：本文中使用了以异甘草酸为基础的双官能团一次胺-苯并二酮有机催化剂，在硝基烯烃和苯乙酮的Michael加成反应中应用。在室温下观察到两种构型的共轭加成异构体，收率高（高达93%）且对映选择性良好（高达91% ee）。
• Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
  作者：Jesús Flores-Ferrándiz、Alexander Stiven、Lia Sotorríos、Enrique Gómez-Bengoa、Rafael Chinchilla

  DOI：10.1016/j.tetasy.2015.07.011

  日期：2015.9

  Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched beta-substituted gamma-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction. (C) 2015 Elsevier Ltd. All rights reserved.