3-((4-chlorophenyl)amino)-1-phenyl-3-(p-tolyl)propan-1-one | 100410-41-1

• 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-chlorophenyl)amino)-1-phenyl-3-(p-tolyl)propan-1-one
• 英文别名: Phenyl-(β-4-chlor-anilino)-β-(4-tolyl-ethyl)-keton；3-(4-Chloroanilino)-3-(4-methylphenyl)-1-phenylpropan-1-one
• CAS: 100410-41-1
• 化学式: C₂₂H₂₀ClNO
• 分子量: 349.86
• InChiKey: PRWPKVGSHVCXAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 对氯苯胺 在 magnesia 作用下， 反应 1.33h， 以95%的产率得到3-((4-chlorophenyl)amino)-1-phenyl-3-(p-tolyl)propan-1-one
  参考文献：
  名称：

  MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction

  摘要：

  通过改进的溶胶-凝胶技术制备的MgO纳米颗粒具有较窄的粒径分布。合成的氧化镁纳米颗粒在无溶剂条件下于室温下作为高效催化剂，用于一系列α,β-不饱和羰基化合物和硝基烯烃的氮迈克尔加成反应中，以及胺的加成反应，从而获得高产率的β-氨基羰基和β-硝基胺。该催化剂可回收并在至少五次连续运行中重复使用而不会损失活性。

  DOI：

  10.1007/s13738-013-0338-x

文献信息

• Hf(OTf)4 as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
  作者：Shuai-Bo Han、Jing-Ying Wei、Xiao-Chong Peng、Rong Liu、Shan-Shan Gong、Qi Sun

  DOI：10.3390/molecules25020388

  日期：——

  Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the

  Hf(OTf)4 被确定为在无溶剂条件下进行三组分曼尼希反应的高效催化剂（0.1-0.5 mol%）。当使用烷基酮作为底物时，Hf(OTf)4 催化的曼尼希反应表现出优异的区域选择性和非对映选择性。酮在 MeOH-d4 中的 H/D 交换反应的 1H NMR 示踪表明 Hf(OTf)4 可以显着促进酮-烯醇互变异构化，从而有助于加快反应速率。
• Brønsted–Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions
  作者：Hong Bo Wang、Nan Yao、Long Wang、Yu Lin Hu

  DOI：10.1039/c7nj02541f

  日期：——

  Novel mesoporous silica supported ILs have been prepared and successfully applied as a heterogeneous catalyst in Mannich reactions. The excellent recyclability of the supported catalyst, mild reaction conditions, good to excellent yields, low catalyst loading, and operational simplicity are the important features of this methodology.

  已经制备了新型介孔二氧化硅负载的IL，并将其成功用作曼尼希反应中的多相催化剂。该方法的重要特点是负载的催化剂具有出色的可回收性，温和的反应条件，良好的产率至极好的产率，低的催化剂负载量以及操作简便性。
• Solvent-free synthesis of β-amino ketones using carboxyl-functionalized poly(ionic liquid) at room temperature
  作者：Avinash Ganesh Khiratkar、Kamlesh Rudreshwar Balinge、Karan Jivanlal Bhansali、Pundlik Rambhau Bhagat

  DOI：10.1007/s11164-017-3134-x

  日期：2018.2

  Abstract Carboxyl-functionalized poly(ionic liquid) (CFPIL) was easily synthesized from its starting material and characterized by Fourier transform infrared spectroscopy, thermal gravimetric analysis and elemental analysis. The synthesized CFPIL was used as an efficient heterogeneous catalyst for the synthesis of β-amino ketones by three-component one-pot Mannich reaction between various aromatic

  摘要 羧基官能化聚离子液体（CFPIL）易于从其起始原料合成，并通过傅里叶变换红外光谱，热重分析和元素分析进行​​表征。所合成的CFPIL被用作高效的非均相催化剂，通过在室温下在无溶剂条件下，各种芳族醛与胺和苯乙酮之间的三组分单锅曼尼希反应，合成β-氨基酮。研究了催化剂用量和反应时间的影响。结果表明，CFPIL具有良好至中等的催化活性和可重复使用性。催化过程很简单，可以很容易地通过过滤回收催化剂，并用乙醇洗涤以再用于下一个实验，而不会明显丧失催化活性。 图形概要
• Reusable 1,2,4-Triazolium Based Brønsted Acidic Room Temperature Ionic Liquids as Catalyst for Mannich Base Reaction
  作者：Sankaranarayanan Nagarajan、Elango Kandasamy

  DOI：10.1007/s10562-014-1312-7

  日期：2014.9

  Unprecedented examples of 1-alkyl-1,2,4-triazolium methanesulfonate based Brønsted acidic room temperature ionic liquids were synthesized and characterized. Their catalytic activity and efficiency in recyclability and reusability on one pot synthesis of halide substituted β-amino carbonyl compounds are reported.Graphical Abstract

  合成并表征了基于 Brønsted 酸性室温离子液体的 1-烷基-1,2,4-三唑鎓甲磺酸盐的前所未有的实例。报道了它们在卤化物取代的 β-氨基羰基化合物的一锅合成中的催化活性和可回收性和可重复使用性的效率。 图形摘要
• An Efficient Synthesis of 1,3-Diphenyl-3-phenylamino-propan-1-one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS-PCS) as Catalyst
  作者：Aida Mansoori、Hossein Eshghi、Jalil Lari

  DOI：10.1002/jccs.201700095

  日期：2018.5

  catalysts. In this work, the reaction between acetophenone, aromatic aldehydes, and aromatic amines has been efficiently catalyzed by porous carbon spheres which were doped by nitrogen and sulfur (NS‐PCS) at ambient temperature to give diverse β‐amino carbonyl compounds in nearly high yields.

  通过曼尼希反应合成β-氨基羰基化合物涉及在单个作用中创建各种键，作为扩展分子卷积和多功能性的最强大的合成工具之一，引起了极大的关注。碳球（CSs）结合了碳材料与球形胶体的优点，这使它们具有许多独特的催化剂特性。在这项工作中，苯乙酮，芳香醛和芳香胺之间的反应已被多孔碳球有效地催化，该多孔碳球在环境温度下被氮和硫（NS-PCS）掺杂，以高收率得到各种β-氨基羰基化合物。