1-(4-methoxyphenyl)-3-phenyl-3-(phenylamino)propan-1-one | 856-19-9

• 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: 1-(4-methoxyphenyl)-3-phenyl-3-(phenylamino)propan-1-one
• 英文别名: 3-Anilino-1-(4-methoxyphenyl)-3-phenylpropan-1-one
• CAS: 856-19-9
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: OTJZOJJFBIXHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 对甲氧基苯乙酮 在 potassium phosphate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 1-(4-methoxyphenyl)-3-phenyl-3-(phenylamino)propan-1-one
  参考文献：
  名称：

  K3PO4-catalyzed one-pot synthesis of β-amino ketones

  摘要：

  A new strategy which uses cheap K3PO4 as a very effective catalyst has been developed for synthesis of beta-amino ketones by one-pot reaction of an aryl aldehyde, acetophenone derivative, and amine in EtOH at room temperature.

  DOI：

  10.1007/s00706-012-0729-1

文献信息

• Salicylato Titanocene Complexes as Cooperative Organometallic Lewis Acid and Brønsted Acid Catalysts for Three-Component Mannich Reactions
  作者：Ya Wu、Chun Chen、Gai Jia、Xuyang Zhu、Huaming Sun、Guofang Zhang、Weiqiang Zhang、Ziwei Gao

  DOI：10.1002/chem.201402438

  日期：2014.7.7

  A binary acid system has been developed that features an air‐stable organometallic precursor, titanocene dichloride, and simple organic cooperative Brønsted acids, which allowed for mild and highly efficient Mannich reactions of both aryl and alkyl ketones with excellent yields and satisfactory diastereoselectivity. Mechanistic studies, including 1H NMR titration, X‐ray structure analyses as well as

  已经开发了一种二元酸体系，其特征是具有空气稳定性的有机金属前体，二茂钛二氯化物和简单的有机协作布朗斯台德酸，可实现芳基和烷基酮的温和高效的曼尼希反应，并具有优异的收率和令人满意的非对映选择性。机理研究，包括1 H NMR滴定，X射线结构分析以及催化活性物质的分离，阐明了这种新的二元酸体系的巨大协同作用。
• Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecylsulfate (SDS) Upon a Three-Component Reaction of Aldehydes, Amines, and Ketones Under Neutral Conditions
  作者：Abbas Ali Jafari、Fatemeh Moradgholi、Fatemeh Tamaddon

  DOI：10.1002/ejoc.200801037

  日期：2009.3

  A micellar solution of anionic, cationic or neutral surfactants can be used as an excellent medium for three-component Mannich reactions of aldehydes, amines, and ketones at room temperature. Sodium dodecylsulfate turned out to efficiently catalyze the reaction in neutral pure water (pH ≈ 7), and the corresponding desired β-amino ketones precipitate while the reactions proceedes. This method provides

  阴离子、阳离子或中性表面活性剂的胶束溶液可用作醛、胺和酮在室温下进行三组分曼尼希反应的优良介质。结果证明十二烷基硫酸钠在中性纯水 (pH ≈ 7) 中有效催化反应，并且在反应进行时相应的所需 β-氨基酮沉淀。该方法在温和的反应条件、干净的反应曲线、提高的产率和优异的区域选择性和非对映选择性方面提供了一种新的改进的三组分曼尼希反应，后处理简单。观察到在水中中性条件下点击化学的有趣例子。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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。
• Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition
  作者：M. D. Prabhakara、Barnali Maiti

  DOI：10.1007/s11164-020-04096-w

  日期：2020.4

  Abstract A highly efficient clean and simple methodology has been established for the one-pot Mannich reaction using ionic liquid-immobilized proline(s) organocatalyst under solvent-free conditions. The three components comprising substituted acetophenones, substituted aromatic aldehydes and substituted aromatic amines underwent Mannich reactions in the presence of 7 mol% of ionic liquid-immobilized

  摘要 对于无溶剂条件下使用离子液体固定的脯氨酸有机催化剂的单锅曼尼希反应，已经建立了一种高效，清洁，简便的方法。含有取代的苯乙酮，取代的芳族醛和取代的芳族胺的三种组分在7 mol％离子液体固定的脯氨酸有机催化剂存在下进行曼尼希反应，可在室温下2-3小时内提供β-氨基羰基化合物优异的产量。该方法具有许多优点，例如反应条件温和，反应时间短，催化剂负载率低，多组分方法，无过渡金属和无溶剂合成。 图形摘要
• Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction
  作者：Nagappan Saravana Ganesan、Palaniswamy Suresh

  DOI：10.1007/s11164-020-04324-3

  日期：2021.3

  preparable graphene oxide (GO) is used as a straightforward carbocatalyst for the synthesis of β -amino ketones via a 3-component Mannich reaction under mild condition. The native GO is acting as a carbonaceous solid Brønsted acid catalyst without any special functionalization, yielding a spectrum of β -amino ketones under metal-free conditions. The present catalytic method offers a benign and simple procedure

  摘要 简单且易于制备的氧化石墨烯 (GO) 被用作直接的碳催化剂，用于在温和条件下通过 3 组分曼尼希反应合成 β-氨基酮。天然 GO 充当碳质固体布朗斯台德酸催化剂，无需任何特殊功能化，在无金属条件下产生一系列 β-氨基酮。本催化方法提供了一种良性且简单的程序，没有任何危险的后处理，并且色谱纯化导致β-氨基酮的高产率。该催化剂在连续 6 次催化循环中表现出良好的可持续性，而其活性没有任何显着损失。通过FT-IR、PXRD、SEM和TEM等分析技术证明了回收催化剂的稳定性。这种温和的固体酸催化剂提供了一种替代且可持续的方法，可以在更环保的条件下获得合成必需的 β-氨基酮。图形概要