4-(4-chlorophenyl)-4-(phenylamino)butan-2-one | 113360-54-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-chlorophenyl)-4-(phenylamino)butan-2-one
• 英文别名: 4-phenylamino-4-(4-chlorophenyl)butan-2-one；4-Anilino-4-(4-chlorophenyl)butan-2-one
• CAS: 113360-54-6
• 化学式: C₁₆H₁₆ClNO
• 分子量: 273.762
• InChiKey: JYQQNPXNJSIZIA-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  422.0±35.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Aniline;anilino-(4-chlorophenyl)methanesulfonic acid 、 丙酮 以94%的产率得到
  参考文献：
  名称：

  KRASNOV V. L.; MATYUKOV E. V.; BODRIKOV I. V., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 30,(1987) N 5, 38-41

  摘要：

  DOI：

文献信息

• Highly Efficient One-Pot, Three-Component Synthesis of β-Aminoketones Catalyzed by Fe(O₂CCF₃)₃
  作者：Min Zhang、Biao Xiong、Wei Yang、Ling Chen、Feng Wu、Quan Wang、Yuqiang Ding

  DOI：10.1080/00397911.2011.569866

  日期：2012.10

  Abstract A highly efficient one-pot, three-component synthesis of β-aminoketones was demonstrated using the cost-effective, noncorrosive, and easily available Fe(O2CCF3)3 as a catalyst for the first time. The method can be employed to synthesize a wide range of target compounds and to introduce different functional groups into the β-aminoketone skeleton. Additionally, the method consistently has the

  摘要 首次使用具有成本效益、无腐蚀性且易得的 Fe(O2CCF3)3 作为催化剂，证明了一种高效的一锅三组分 β-氨基酮合成方法。该方法可用于合成范围广泛的目标化合物并将不同的官能团引入β-氨基酮骨架。此外，该方法始终具有收率好、反应时间短、实验后处理简单等优点，是合成功能化β-氨基酮的有效方法。图形概要
• Solvent strategy for unleashing the Lewis acidity of titanocene dichloride for rapid Mannich reactions
  作者：Ya Wu、Xiu Wang、Yanlong Luo、Jing Wang、Yajun Jian、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1039/c5ra27094d

  日期：——

  The remarkable activation effect of alcohol solvent on kinetically inert titanocene dichloride was found to promote rapid three-component Mannich reactions. NMR and ESI-MS analyses as well as a control experiment of catalytic active species elucidated that the coordination of MeOH to the titanocene moiety unleashed the Lewis acid [Cp2Ti(OMe)2] and Brønsted acid HCl, which led to the enhanced catalytic

  发现醇溶剂对动力学惰性二茂钛二氯化物的显着活化作用促进了快速的三组分曼尼希反应。NMR和ESI-MS分析以及催化活性物种的对照实验表明，MeOH与二茂钛部分的配位释放出路易斯酸[Cp 2 Ti（OMe）2 ]和布朗斯台德HCl，从而增强了催化作用Cp 2 TiCl 2的活性。
• Cooperative Catalysis of <i>p</i>-Aminophenol and Titanocene Dichloride in Direct Mannich Reactions with Acetone
  作者：Xuyang Zhu、Chun Chen、Binxun Yu、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1246/cl.140705

  日期：2014.12.5

  A new binary acid system featuring an air stable organometallic precursor, titanocene dichloride and a simple Brønsted acid–base compound, was developed. The new catalyst system allowed for mild and highly efficient direct three-component Mannich reactions of both aryl ketones and alkyl ketones, in particular, acetone and its derivatives with excellent yields. Mechanistic study elucidated the dramatic synergistic effect of the new binary acid system.

  开发了一种新型的二元酸体系，包含一种空气稳定的有机金属前驱体——二氯化钛烯，以及一种简单的布朗斯特酸碱化合物。该新催化剂体系使得芳香酮和烷基酮，特别是丙酮及其衍生物的直接三组分曼尼赫反应能够在温和的条件下高效进行，得到了优异的产率。机制研究阐明了这种新二元酸体系的显著协同效应。
• Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a “one-pot” synthesis
  作者：Kun Li、Ting He、Chao Li、Xing-Wen Feng、Na Wang、Xiao-Qi Yu

  DOI：10.1039/b817524a

  日期：——

  A novel lipase-catalysed direct Mannich reaction has been developed under aqueous conditions in a “one-pot” strategy. Interestingly, these promiscuous reactions can be greatly promoted by water and generally require aromatic aldehydes.

  一种新型的脂肪酶催化直接 曼尼希反应在水性条件下以“一锅法”开发。有趣的是，这些混杂反应可以通过水 通常需要芳族醛。
• Deep Eutectic Solvent as a Recyclable Catalyst for Three-Component Synthesis of β-Amino Carbonyls
  作者：Fariba Keshavarzipour、Hossein Tavakol

  DOI：10.1007/s10562-014-1471-6

  日期：2015.4

  We have reported one-pot, three-component Mannich type reaction of aldehyde, amines and ketone (acetone and acetophenones), catalyzed by deep eutectic solvent (choline chloride/zinc chloride) at room temperature to give beta-amino carbonyls in good yields. The catalyst could be recycled at least four times without remarkable decrease in its catalytic activity. The general method is easy, fast and environmental friendly.