3-((4-bromophenyl)amino)-1,3-diphenylpropan-1-one | 801-03-6

• 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-((4-bromophenyl)amino)-1,3-diphenylpropan-1-one
• 英文别名: 3-(4-bromophenylamino)-1,3-diphenylpropan-1-one；3-(4-bromoanilino)-1,3-diphenyl-1-propanone；β-(4-Brom-anilino)-β-phenyl-propiophenon；β-4-Bromanilino-β-phenyl-propiophenon；1,3-Diphenyl-3-(4-bromoanilino)-1-propanone；3-(4-bromoanilino)-1,3-diphenylpropan-1-one
• CAS: 801-03-6
• 化学式: C₂₁H₁₈BrNO
• 分子量: 380.284
• InChiKey: OWCUFVPBXFRRPV-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  苯乙酮 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 3-((4-bromophenyl)amino)-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  Design, and facile synthesis of 1,3 diaryl-3-(arylamino)propan-1-one derivatives as the potential alpha-amylase inhibitors and antioxidants

  摘要：

  Diabetes is the most prevalent metabolic disorder causing a high rate of mortality and morbidity. Recently alpha-amylase is reported to be good drug design target for the treatment of diabetes mellitus. We have designed 116 molecules based on aza-Michael adduct of trans-chalcone as 1,3 diaryl-3-(arylamino)propan-1-ones which were studied by molecular docking and among them best six derivatives were synthesized easily via aza-Michael addition on trans-chalcone using KOH as a catalyst and evaluated for alpha-amylase inhibition along with antioxidant activity. It was observed that all compounds have alpha-amylase inhibitory activity but at different extents. The molecule 3e is the most potent alpha-amylase inhibitor of this series. 3a is the second most potent compound, whereas only one molecule 3d has shown antioxidant activity.

  DOI：

  10.1016/j.bioorg.2018.10.010

文献信息

• Fe3O4@saponin/Cd: a novel magnetic nano-catalyst for the synthesis of β-aminoketone derivatives
  作者：Marzieh Kiani、Hossein Anaraki-Ardakani、Neda Hasanzadeh、Ayeh Rayatzadeh

  DOI：10.1007/s13738-020-01918-x

  日期：2020.9

  electron microscopy (HR-TEM), and Brunauer–Emmett–Teller (BET). It was found that the catalyst was active for the synthesis of β-aminoketone derivatives via one-pot three-component Mannich-type reactions of ketones, aromatic aldehydes, aromatic amines under eco-friendly solvent, at room temperature. Furthermore, this catalyst can be easily recovered magnetically and can be reused for other runs without any

  一种新颖的可回收磁性核-壳纳米颗粒的Fe 3 ö 4 @皂苷/ CD用纳米Fe的组合合成的3 ö 4 @saponin用乙酸镉。磁性纳米粒子（MNP）Fe 3 O 4的结构，磁性特征和形态皂苷/镉通过不同的实验进行了全面研究，例如傅立叶变换红外光谱（FT-IR），能量色散X射线光谱（EDS），热重分析（TGA），X射线衍射（XRD），振动样品磁力计（VSM），扫描电子显微镜（SEM），电感耦合等离子体（ICP），高分辨率透射电子显微镜（HR-TEM）和Brunauer-Emmett-Teller（BET）。发现该催化剂在室温下通过酮，芳族醛，芳族胺的一锅三组分曼尼希型反应对合成β-氨基酮衍生物具有活性 。此外，该催化剂可以容易地磁性回收，并且可以在不降低活性的情况下再次用于其他运行。
• PPh3-catalyzed Mannich reaction: a facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature
  作者：Javad Abedini-Torghabeh、Hossein Eshghi、Mehdi Bakavoli、Mohammad Rahimizadeh

  DOI：10.1007/s11164-013-1478-4

  日期：2015.6

  PPh3 was used as an efficient catalyst for the one-pot three-component Mannich reactions of acetophenone with different aromatic amines and aromatic aldehydes under solvent-free conditions at room temperature. This method provides a novel and improved method for preparing β-amino carbonyl compounds in the absence of acidic catalyst in excellent yield. Little catalyst loading, easy accessibility of the catalyst, mild conditions, and simple work-up procedure are the main features of this protocol.

  三苯基膦（PPh3）作为高效催化剂，在室温无溶剂条件下，用于苯乙酮与不同芳香胺和芳香醛的一锅三组分曼尼希反应。该方法在没有酸性催化剂的情况下，提供了一种新颖且改进的制备β-氨基羰基化合物的方法，产率优异。催化剂用量少、易获取催化剂、条件温和、操作简便是其主要特点。
• 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。
• The Mannich Reaction Between Aromatic Ketones, Aromatic Aldehydes and Aromatic Amines
  作者：Yi Lin、Lei Huangshu、Zou Junhua、Xu Xiujuan

  DOI：10.1055/s-1991-26554

  日期：——

  The acid-catalyzed Mannich reaction of acetophenones with benzaldehyde derivatives and aromatic amines gives 1,3-diaryl-3-(arylamino)propanones in high yield.

  酸催化的Mannich反应中，醋酰苯与苯甲醛衍生物和芳香胺反应，能够高产率地生成1,3-二芳基-3-(芳香氨基)丙酮。
• 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