1,3-二苯基-3-[(2-硝基苯基)氨基]丙烷-1-酮 | 1030387-94-0

• 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
• 中文名称: 1,3-二苯基-3-[(2-硝基苯基)氨基]丙烷-1-酮
• 英文名称: 1,3-diphenyl-3-[(2-nitrophenyl)amino]propan-1-one
• 英文别名: 3-(2-Nitroanilino)-1,3-diphenylpropan-1-one
• CAS: 1030387-94-0
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: NHWZSALDNGEROM-UHFFFAOYSA-N

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：

  苯甲醛 、 2-硝基苯胺 、 苯乙酮 在 cellulose SILP catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以69%的产率得到1,3-二苯基-3-[(2-硝基苯基)氨基]丙烷-1-酮
  参考文献：
  名称：

  纤维素负载的离子液相催化剂介导的曼尼希反应

  摘要：

  制备了带有樟脑烯基侧基的樟脑磺酸根阴离子的纤维素负载离子液相催化剂，并采用不同的分析技术进行了表征，如傅立叶变换红外光谱，傅立叶变换拉曼光谱和交叉极化-魔角纺丝（CP- MAS）13 C NMR光谱，X射线衍射，扫描电子显微镜和热重分析。SILP催化剂在通过曼尼希反应合成β-氨基羰基化合物中显示出优异的催化活性。回收研究表明，SILP催化剂可以重复使用六次，而催化活性不会显着降低。

  DOI：

  10.1071/ch18576

文献信息

• 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。
• Bromodimethylsulfonium Bromide Catalyzed Three-Component Mannich-Type Reactions
  作者：Abu T. Khan、Tasneem Parvin、Lokman H. Choudhury

  DOI：10.1002/ejoc.200700643

  日期：2008.2

  Bromodimethylsulfonium bromide catalyzes Mannich-type reactions of a variety of aldimines, generated in situ from aldehydes and anilines, with enolizable ketones or diethyl malonate in three-component reactions to afford the corresponding β-amino carbonyl compounds. The salient features of this protocol are: shorter reaction times, simplicity of the procedure, good to excellent yields, avoidance of

  溴化二甲基锍溴化物催化由醛和苯胺原位生成的各种醛亚胺的曼尼希型反应，与可烯醇化的酮或丙二酸二乙酯在三组分反应中得到相应的 β-氨基羰基化合物。该方案的显着特点是：反应时间更短、程序简单、产率好到极好、避免了水处理和柱色谱分离，以及高立体选择性。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim , 德国, 2008)
• Ultrasound-Promoted One-Pot Three-Component Synthesis of β–Amino Carbonyl Compounds Using Manganese Perchlorate
  作者：Bhupinder Kaur、Harish Kumar

  DOI：10.1080/00304948.2020.1805995

  日期：2020.9.2

  The Mannich reaction is a key method for C-C bond formation leading to β-amino carbonyl compounds, which are important intermediates for diverse pharmaceuticals and natural products. 1 , 2 However,...

  曼尼希反应是形成 CC 键的关键方法，导致 β-氨基羰基化合物，这是多种药物和天然产物的重要中间体。1 , 2 然而，...
• Bis[(L)prolinato-N,O]Zn in acetic acid-water: a novel catalytic system for the synthesis of β-amino carbonyls via Mannich reaction at room temperature
  作者：Mazaahir Kidwai、Arti Jain、Roona Poddar、Saurav Bhardwaj

  DOI：10.1002/aoc.1764

  日期：2011.5

  Zn[(L)proline]2 was used as an efficient catalyst for the one‐pot multicomponent reactions (MCR) of different aromatic amines, aromatic aldehyde and ketones in aqueous media. This method provides a novel and improved method for obtaining stereoselective β‐amino carbonyl compounds in terms of good yield. Little catalyst loading, recyclability, easy accessibility of the catalyst and aqueous media are

  Zn [（L）脯氨酸] 2用作水性介质中不同芳族胺，芳族醛和酮的单锅多组分反应（MCR）的有效催化剂。该方法为获得立体选择性β-氨基羰基化合物提供了一种新颖且改进的方法，具有良好的收率。该方案的主要特点是催化剂用量少，可循环利用，催化剂和水性介质易于进入。此外，由于粗产物本身是非常纯的，因此不需要柱色谱法和产物重结晶。首次获得了催化剂的粉末XRD和TEM图像。版权所有©2011 John Wiley＆Sons，Ltd.
• Entirely green protocol for the synthesis of β-aminoketones using saccharose as a homogenous catalyst
  作者：Mir Rasul Mousavi、Nourallah Hazeri、Malek Taher Maghsoodlou、Sajjad Salahi、Sayyed Mostafa Habibi-Khorassani

  DOI：10.1016/j.cclet.2013.03.022

  日期：2013.5

  Saccharose was applied as an efficient and homogenous catalyst for a one-pot, three-component Mannich reaction for the formation of beta-aminoketones from aromatic aldehydes, anilines, and acetophenone at ambient temperature in excellent yields. This protocol has the following advantages: mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign and simple work-up procedures. (C) 2013 Nourallah Hazeri. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.