3-苯胺基-3-(4-溴苯基)-1-苯基丙烷-1-酮 | 119948-35-5

• 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
• 中文名称: 3-苯胺基-3-(4-溴苯基)-1-苯基丙烷-1-酮
• 英文名称: 3-(4-bromophenyl)-1-phenyl-3-(N-phenylamino)propan-1-one
• 英文别名: 3-(4-bromophenyl)-1-phenyl-3-(phenylamino)propan-1-one；3-Anilino-3-(4-bromophenyl)-1-phenylpropan-1-one
• CAS: 119948-35-5
• 化学式: C₂₁H₁₈BrNO
• 分子量: 380.284
• InChiKey: XOIKMJKNTTZMIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-苯胺基-3-(4-溴苯基)-1-苯基丙烷-1-酮 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到4′-溴查耳酮
  参考文献：
  名称：

  铟（III）的三氟甲磺酸盐催化查尔酮的Aza-Michael加合物与芳香胺的反应：Retro-Michael加成与喹啉的形成

  摘要：

  研究了查尔酮的氮杂-迈克尔加合物与芳族胺的三氟甲磺酸铟（III）催化反应。衍生自取代苯胺和查耳酮的迈克尔加合物进行了逆迈克尔加成反应，得到了原始原料，而衍生自1-萘胺和查耳酮的迈克尔加合物得到了喹啉。有人提出了六元环过渡态来解释反迈克尔加成反应，而提出了一种Povarov机理来解释喹啉的形成。

  DOI：

  10.1021/acs.joc.7b03151
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 (E)-1-(4-bromophenyl)-N-phenylmethanimine 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以75%的产率得到3-苯胺基-3-(4-溴苯基)-1-苯基丙烷-1-酮
  参考文献：
  名称：

  Addition of silylated carbon nucleophiles to iminium and cyclic N-acyliminium ions promoted by InCl3

  摘要：

  InCl3 was used as Lewis acid in the addition of silyl enolates and allyltrimethylsilane to aromatic aldimines and cyclic N-acyliminium ions derived from 5-acetoxylactams affording beta -aminocarbonyl systems and allyl adducts, respectively, in reasonable to good yields. The diastereofacial selectivity of cyclic N-acyliminium ions was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01828-1

文献信息

• Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl)sulfonate complexes as highly efficient and recyclable catalysts for C–C bond forming reactions
  作者：Ningbo Li、Jinying Wang、Xiaohong Zhang、Renhua Qiu、Xie Wang、Jinyang Chen、Shuang-Feng Yin、Xinhua Xu

  DOI：10.1039/c4dt00549j

  日期：——

  A series of titanocene perfluoroalkyl(aryl)sulfonate complexes were synthesized, characterized, and applied in various C–C bond forming reactions.

  一系列的钛ocene基过氟烷基（芳基）磺酸盐配合物被合成、表征，并应用于各种C-C键形成反应。
• Highly Efficient One-Pot Three-Component Mannich Reaction in Water Catalyzed by Heteropoly Acids
  作者：Najmodin Azizi、Lalleh Torkiyan、Mohammad R. Saidi

  DOI：10.1021/ol060498v

  日期：2006.5.1

  [reaction: see text] Heteropoly acids efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different amines in water at ambient temperature and afforded the corresponding beta-amino carbonyl compounds in good to excellent yields and with moderate diastereoselectivity. This method provides a novel and improved modification of the three-component

  [反应：参见文本]杂多酸可在环境温度下有效催化酮与芳香醛和不同胺在水中的一锅三组分曼尼希反应，并以良好或优异的收率和中等收率提供相应的β-氨基羰基化合物非对映选择性。该方法在温和的反应条件和干净的反应曲线方面，使用非常少量的催化剂和简单的后处理程序，就对三组分曼尼希反应进行了新颖和改进的改进。
• One-Pot Silyl Ketene Acetal-Formation Mukaiyama-Mannich Additions to Imines Mediated by Trimethylsilyl Trifluoro­methanesulfonate
  作者：C. Wade Downey、Jared A. Ingersoll、Hadleigh M. Glist、Carolyn M. Dombrowski、Adam T. Barnett

  DOI：10.1002/ejoc.201500958

  日期：2015.11

  the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base, thioesters are readily converted into silyl ketene acetals in situ and undergo Mukaiyama–Mannich addition to N-phenylimines in one pot. The silyl triflate appears to play two roles, activating both the thioester and the imine. This process also works well when thioesters are replaced with amides, esters, or ketones. Products

  在三氟甲磺酸三甲基甲硅烷基酯和三烷基胺碱的存在下，硫酯很容易原位转化为甲硅烷基乙烯酮缩醛，并在一锅中对 N-苯基亚胺进行 Mukaiyama-Mannich 加成。甲硅烷基三氟甲磺酸酯似乎起到两个作用，激活硫酯和亚胺。当硫酯被酰胺、酯或酮取代时，该过程也能很好地工作。产品以脱甲硅烷基苯胺形式分离，无需脱保护步骤。收率范围为 65% 至 99%。
• Mannich reactions catalyzed by perchloric acid in Triton X10 aqueous micelles
  作者：Guo-ping Lu、Chun Cai

  DOI：10.1016/j.catcom.2010.02.007

  日期：2010.3

  Perchloric acid can efficiently catalyze the one-pot, three-component Mannich reactions of ketones with aromatic aldehydes and aromatic amines in Triton X10 aqueous micelles at room temperature. This protocol has several advantages such as excellent yields, mild conditions, clear reaction profile and simple work-up procedure.

  高氯酸可在室温下有效地催化酮与芳族醛和芳族胺的一锅三组分曼尼希反应。该方案具有许多优点，例如产率高，条件温和，反应曲线清晰和后处理程序简单。
• Rice-husk-supported FeCl3 nano-particles: Introduction of a mild, efficient and reusable catalyst for some of the multi-component reactions
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah

  DOI：10.1016/j.crci.2013.02.019

  日期：2013.10

  Résumé Rice-husk-supported FeCl3 nano-particles (FeCl3–RiH) were prepared and used as an environmentally friendly catalyst in the synthesis of β-amino carbonyl compounds, 1,8-dioxo-octahydro xanthenes, and bis-indolyl methanes from simple and readily available precursor molecules.

  简历 Rice-husk-supported FeCl3 nano-particles，即FeCl3–RiH纳米粒子，已成功制备并用作环境友好型催化剂，在合成β-氨基羰基化合物、1,8-二氧杂八氢化咕吨和双吲哚基甲烷的过程中，它们能够高效催化来自简单且易于获得的起始分子。