1,3-diphenyl-3-[(4-nitrophenyl)amino]propan-1-one | 804-20-6

• 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: 1,3-diphenyl-3-[(4-nitrophenyl)amino]propan-1-one
• 英文别名: 3-((4-nitrophenyl)amino)-1,3-diphenylpropan-1-one；3-(4-nitro-phenylamino)-1,3-diphenyl-propan-1-one；3-(4-nitrophenylamino)-1,3-diphenyl-propan-1-one；1,3-diphenyl-3-(p-nitrophenylamino)-1-propanone；3-(4-nitrophenylamino)-1,3-diphenylpropan-1-one；3-(4-nitrophenylamino)-1,3-diphenylpropanone；3-(4-nitroanilino)-1,3-diphenylpropan-1-one
• CAS: 804-20-6
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: YSGOODBDQZEEOO-UHFFFAOYSA-N

物化性质

• 熔点：
  184 °C
• 沸点：
  562.8±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-3-[(4-nitrophenyl)amino]propan-1-one 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以89%的产率得到反式-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：

  苯乙酮 在 potassium phosphate 作用下， 以 乙醇 为溶剂， 反应 1.58h， 生成 1,3-diphenyl-3-[(4-nitrophenyl)amino]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

• Strong Lewis Acids of Air-Stable Metallocene Bis(perfluorooctanesulfonate)s as High-Efficiency Catalysts for Carbonyl-Group Transformation Reactions
  作者：Renhua Qiu、Xinhua Xu、Lifeng Peng、Yalei Zhao、Ningbo Li、Shuangfeng Yin

  DOI：10.1002/chem.201103874

  日期：2012.5.14

  that 2 a and 2 b were thermally stable at 300 and 180 °C, respectively. These complexes exhibited unusually high solubility in polar organic solvents. Conductivity measurement showed that the complexes (2 a and 2 b) were ionic dissociation in CH3CN solution. X‐ray analysis result confirmed 2 a⋅3 H2O⋅THF was a cationic organometallic Lewis acid. UV/Vis spectra showed a significant red shift due to the

  强路易斯酸空气中稳定的金属茂双（全氟辛烷磺酸盐）S [M（CP）2 ] [OSO 2 C ^ 8 ˚F 17 ] 2 ⋅ Ñ ħ 2 O⋅THF（M = Zr的（2 ⋅3ħ 2 O⋅THF ），M =的Ti（图2b ⋅2ħ 2 O⋅THF））由[M（CP）的反应合成2 ]氯2（M = Zr的（1），M =的Ti（图1b）），与n BuLi和C 8 F 17 SO 3 H（2当量）或与C 8 F 17 SO 3Ag（2当量）。这些配合物的水合物数（n）是可变的，取决于条件从0变为4。与众所周知的茂金属三氟甲磺酸盐相反，这些络合物在露天环境中一年没有变化。热重-差示扫描量热（TG-DSC）分析表明，2和图2b分别为300和180℃，是热稳定的。这些配合物在极性有机溶剂中显示出异常高的溶解度。电导率测量表明，络合物（2a和2b）在CH 3 CN溶液中呈离子离解。X射线分析结果确认为2 a⋅3H
• Bi(NO3)3•5H2O: An Efficient and Green Catalyst for Synthesis of 1,5-Benzodiazepines and b-Amino Carbonyl Compounds
  作者：Jaspreet Kaur Rajput、Gagandeep Kaur

  DOI：10.14233/ajchem.2013.14353

  日期：——

  Bismuth nitrate pentahydrate is found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines and b-amino carbonyl compounds using condensation of o-phenylenediamine with ketones and one pot three component Mannich reaction, respectively under solvent free conditions at room temperature. This method offers a simple, solvent free, room temperature, environment friendly synthesis of 1,5-benzodiazepines and b-amino carbonyl compounds. The products are isolated by column chromatography and recrystallization, respectively and were characterized by their melting point, IR and 1H NMR spectroscopy.

  五水合硝酸铋被发现是一种高效的催化剂，可在无溶剂、室温条件下分别通过邻苯二胺与酮的缩合反应以及一锅法三组分曼尼希反应合成1,5-苯二氮杂卓和β-氨基羰基化合物。这种方法提供了一种简单、无溶剂、室温、环境友好的合成1,5-苯二氮杂卓和β-氨基羰基化合物的方式。产物分别通过柱层析和重结晶进行分离，并利用熔点、红外光谱和核磁共振氢谱进行表征。
• Synthesis and structure of an air-stable μ2-hydroxy-bridged binuclear complex of bis(methylcyclopentadienyl)dizirconium(IV) perfluorooctanesulfonate and its application in Lewis acid-catalyzed reactions
  作者：Xiaohong Zhang、Cong Lou、Ningbo Li、Xinhua Xu、Renhua Qiu、Shuangfeng Yin

  DOI：10.1016/j.jorganchem.2013.10.004

  日期：2014.1

  Air-stable binuclear complex of bis(methylcyclopentadienyl)zirconium perfluorooctanesulfonate (1a) was successfully synthesized by the reaction of (CH3Cp)2ZrCl2 with C8F17SO3Ag. The compound 1a was characterized by different techniques and found to have the nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. In addition, its solubility was higher than that of our

  通过（CH 3 Cp）2 ZrCl 2与C 8 F 17 SO 3 Ag反应成功地合成了双（甲基环戊二烯基）全氟辛烷磺酸锆（1a）的空气稳定双核络合物。化合物1a用不同的技术表征，发现具有空气稳定性，耐水性，热稳定性和强路易斯酸度的性质。此外，它的溶解度高于我们先前报道的单核锆茂双（全氟辛烷磺酸盐）的溶解度。它在烷基芳基醚的Friedel-Crafts酰化反应和Mannich反应中显示出很高的催化效率，可以重复使用。
• 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。
• 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。