3-(2-chlorophenyl)-4-nitro-1-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: 3-(2-chlorophenyl)-4-nitro-1-phenylbutan-1-one
• 英文别名: (3R)-3-(2-chlorophenyl)-4-nitro-1-phenylbutan-1-one
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: MJTSSNIMWMIYIF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  苯甲酰基亚甲基三苯基膦 在 N-[3,5-二(三氟甲基)苯基]-N-[(9R)-6-甲氧基-9-二奎宁基]硫脲 作用下， 以 甲苯 为溶剂， 20.0~25.0 ℃ 、900.02 MPa 条件下， 反应 2.0h， 生成 3-(2-chlorophenyl)-4-nitro-1-phenylbutan-1-one
  参考文献：
  名称：

  查尔酮中硝基烷的高压辅助低负荷不对称有机催化共轭加成† ‡

  摘要：

  施加高压（最高9 kbar）可在室温下相对快速地（1-5小时）和硝基甲烷和2-硝基丙烷的对映体1,4-对映体选择性高的加成反应，同时大大降低了催化剂的负载量（0.2-1摩尔％的基于金鸡纳生物碱的硫脲和方酸酰胺）。在9 kbar下以高收率和对映选择性（高达98％）获得了各种γ-硝基酮，而在大气压下的对照实验中，通常在20 h后仅生成少量（<10％）的产物。

  DOI：

  10.1039/c8ob00561c

文献信息

• Asymmetric Conjugate Addition of Nitromethane to Enones Catalyzed by Chiral N,N′-Dioxide-Scandium(III) Complexes
  作者：Liwei Wang、Qi Zhang、Xin Zhou、Xiaohua Liu、Lili Lin、Bo Qin、Xiaoming Feng

  DOI：10.1002/chem.201000688

  日期：——

  Chalk it up as a “Sc”andal: The asymmetric conjugate addition of chalcone and “cinnamone” derivatives to nitromethane has been realized by using a simple and efficient scandium(III)–N,N′‐dioxide complex as the catalyst (see scheme). In the presence of 2–5 mol % catalyst loading, the corresponding products were formed in excellent yields (up to 99 %) and enantioselectivities (up to>99 % ee).

  以“ Sc”形式存在：将查尔酮和“肉桂酮”衍生物不对称共轭加成到硝基甲烷中，是通过使用简单有效的scan（III）-N，N'-二氧化物络合物作为催化剂实现的（参见方案） ）。在2-5 mol％的催化剂负载下，形成的相应产物的收率（高达99％）和对映选择性（高达ee > 99％  ）都非常好。
• Synthesis of a New N-Diaminophosphoryl-N′-[(2S)-2-pyrrolidinylmethyl]thiourea as a Chiral Organocatalyst for the Stereoselective Michael Addition of Cyclohexanone to Nitrostyrenes and Chalcones - Application in Cascade Processes for the Synthesis of Polyc
  作者：Carlos Cruz-Hernández、Eduardo Martínez-Martínez、Perla E. Hernández-González、Eusebio Juaristi

  DOI：10.1002/ejoc.201801339

  日期：2018.12.31

  novel chiral thiourea containing a segment of privileged (2S)‐2‐pyrrolidinylmetan‐amine as well as a hydrophobic phosphoramide framework is described. The new organocatalyst exhibited good performance in asymmetric Michael additions, in a variety of systems including the formal [3+3] cyclization of cyclohexanone with arylidenepyruvates through a cascade process, which involves the asymmetric Michael

  描述了一种新颖的手性硫脲的合成，该硫脲含有一个特权级的（2 S）-2-吡咯烷基二甲胺和疏水性磷酰胺骨架。新型有机催化剂在不对称迈克尔加成反应中表现出良好的性能，在多种系统中，包括通过级联过程与芳基丙酮酸戊酯对环己酮进行正式的[3 + 3]环化反应，该过程涉及不对称迈克尔加成反应/质子转移/非对映选择性醛醇缩合反应。
• 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。
• Organocatalyzed highly stereoselective Michael addition of ketones to alkylidene malonates and nitroolefins using chiral primary-secondary diamine catalysts based on bispidine
  作者：Jie Liu、Zhigang Yang、Xiaohua Liu、Zhen Wang、Yanling Liu、Sha Bai、Lili Lin、Xiaoming Feng

  DOI：10.1039/b910939k

  日期：——

  based on bispidine have been developed to catalyze the asymmetric Michael addition of ketones to alkylidene malonates and nitroalkenes. The corresponding products were obtained in high yields (up to 99%) with high diastereoselectivities (up to 99:1) and high enantioselectivities (up to 97% ee) under mild conditions using either environmentally benign water as the solvent or no solvent.

  已经开发了包含基于联吡啶的伯-仲二胺的有机催化剂以催化酮向亚烷基丙二酸酯和硝基烯烃的不对称迈克尔加成。在温和条件下使用环境友好的方法，可以以高收率（高达99％），高非对映选择性（高达99：1）和高对映选择性（高达97％ee）获得相应的产物。水 作为溶剂或不使用溶剂。
• 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.