(S)-1-(naphthalen-2-yl)-4-nitro-3-phenylbutan-1-one

• 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: (S)-1-(naphthalen-2-yl)-4-nitro-3-phenylbutan-1-one
• 英文别名: (3S)-1-naphthalen-2-yl-4-nitro-3-phenylbutan-1-one
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: RPJKISXTZIMJIX-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  β-硝基苯乙烯 、 2-萘乙酮 在 N-((1R,2R)-2-aminocyclohexyl)-2,4,6-triisopropylbenzenesulfonamide 作用下， 以 甲苯 为溶剂， 以62%的产率得到(S)-1-(naphthalen-2-yl)-4-nitro-3-phenylbutan-1-one
  参考文献：
  名称：

  环己烷-1,2-二胺：酮对硝基烯烃对映选择性共轭加成的有效催化剂

  摘要：

  简单的单磺化环己烷-1,2-二胺是高度对映选择性的有机催化剂，用于酮与硝基烯烃的共轭加成。通过将芳香酮作为最具挑战性的底物，标题反应可以实现高达 98% ee 的选择性。此外，伯胺催化剂、硝基烯烃和酮之间的三组分过程会导致吡咯的不可逆形成，这被认为是催化剂失活的反应途径。 (© Wiley-VCH Verlag GmbH & Co. KGaA , 69451 德国魏因海姆，2009)

  DOI：

  10.1002/ejoc.200801263

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 decarboxylative Michael addition of β-ketoacids to nitroalkenes catalyzed by binaphthyl-derived organocatalysts
  作者：Hyoung Wook Moon、Dae Young Kim

  DOI：10.1016/j.tetlet.2012.09.100

  日期：2012.11

  The catalytic enantioselective decarboxylative Michael addition reaction promoted by chiral bifunctional organocatalysts has been developed, allowing facile synthesis of the corresponding γ-nitro ketones with excellent enantioselectivity (up to 97% ee). The method reported represents a valuable approach utilizing β-ketoacids as synthetic equivalents of aryl methyl ketones.

  已经开发了由手性双官能有机催化剂促进的催化对映选择性脱羧迈克尔加成反应，从而可以容易地合成具有优异对映选择性（最高97％ee）的相应γ-硝基酮。报告的方法代表了一种利用β-酮酸作为芳基甲基酮的合成等同物的有价值的方法。
• Highly Enantioselective Michael Addition of Aromatic Ketones to Nitroolefins Promoted by Chiral Bifunctional Primary Amine-thiourea Catalysts Based on Saccharides
  作者：Kun Liu、Han-Feng Cui、Jing Nie、Ke-Yan Dong、Xiao-Juan Li、Jun-An Ma

  DOI：10.1021/ol0701666

  日期：2007.3.1

  [reaction: see text] A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).

  [反应：见正文]已经开发出一种新型的硫脲催化剂，其将糖和伯胺部分整合到一个小的有机分子中。这些简单的催化剂显示出很高的对映选择性，可直接将芳族迈克尔酮迈克尔加成到一系列硝基烯烃中（最高ee为98％）。
• 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.