1,3-diphenyl-3-(3-nitrophenylamino)-1-propanone | 110194-82-6

• 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-(3-nitrophenylamino)-1-propanone
• 英文别名: 1,3-diphenyl-3-(m-nitrophenylamino)-1-propanone；β-(3-Nitro-anilino)-β-phenyl-propiophenon；3-(3-nitrophenylamino)-1,3-diphenylpropan-1-one；3-(3-nitro-anilino)-1,3-diphenyl-propan-1-one；3-(3-Nitro-anilino)-1,3-diphenyl-propan-1-on；3-[(3-Nitrophenyl)amino]-1,3-diphenylpropan-1-one；3-(3-nitroanilino)-1,3-diphenylpropan-1-one
• CAS: 110194-82-6
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: VRVZPQHFDBAGTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  559.7±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

• 作为产物：
  描述：

  苯乙酮 、 N-亚苄基-3-硝基苯胺 在 乙醇 、 3-硝基苯胺盐酸盐 作用下， 生成 1,3-diphenyl-3-(3-nitrophenylamino)-1-propanone
  参考文献：
  名称：

  Koslow; Schur, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2706,2709;engl.Ausg.S.2673,2675

  摘要：

  DOI：

文献信息

• 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)
• Starch solution as an efficient and environment-friendly catalyst for one-pot synthesis of β-aminoketones and 2,3-dihydroquinazolin-4(1H)-ones in EtOH
  作者：Malek Taher Maghsoodlou、Naimeh Khorshidi、Mir Rasul Mousavi、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani

  DOI：10.1007/s11164-014-1839-7

  日期：2015.10

  An efficient, practical and atom-efficient method has been developed for the preparation of β-aminoketones and 2,3-dihydroquinazoline-4(1H)-ones via multicomponent one-pot reaction in starch solution as an entirely green catalyst. The advantages of this novel protocol are high yields, short reaction time, simple methodology, easy work-up and purification, lack of toxicity and eco-friendly catalyst. .

  一种高效、实用且原子经济的方法已经开发出来，用于通过多组分一锅法反应在淀粉溶液中作为完全绿色催化剂制备β-氨基酮和2,3-二氢喹唑啉-4(1H)-酮。这一新方法的优势在于高产率、短反应时间、简单的方法学、易于后续处理和纯化、无毒性和生态友好型催化剂。
• One-pot three-component Mannich-type reaction catalyzed by trifluoromethanesulfonic acid in water
  作者：Gang Li、Hankui Wu、Zhiyong Wang、Xianli Wang

  DOI：10.1134/s0023158411010113

  日期：2011.2

  One-pot three-component Mannich-type reaction of ketones, aldehydes and amines was efficiently catalyzed by liquid trifluoromethanesulfonic acid in water at ambient temperature. The high yield of corresponding β-amino ketones compounds were achieved. The proposed method is mild, green, simple and efficient.

  在环境温度下，液体三氟甲磺酸在水中能有效地催化酮，醛和胺的一锅三组分曼尼希型反应。实现了高产率的相应β-氨基酮化合物。该方法温和，绿色，简单，有效。
• 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。
• SnCl2-catalyzed three-component one-pot Mannich-type reaction: efficient synthesis of β-aminocarbonyl compounds
  作者：Min Wang、Zhi-Guo Song、Xin Wan、Suang Zhao

  DOI：10.1007/s00706-009-0163-1

  日期：2009.10

  AbstractSnCl2-catalyzed three-component one-pot Mannich reaction of acetophenone or p-chloroacetophenone with different aromatic aldehydes and aromatic amines in ethanol at ambient temperature gave the corresponding β-aminocarbonyl compounds in good to excellent yields. Four new compounds are reported for the first time. Graphical abstract

  摘要在环境温度下，SnCl 2催化苯乙酮或对氯苯乙酮与不同芳族醛和芳族胺在乙醇中的三组分一锅法曼尼希反应，得到相应的β-氨基羰基化合物，收率很好。首次报道了四种新化合物。 图形概要