2-((2-chlorophenylamino)(phenyl)methyl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((2-chlorophenylamino)(phenyl)methyl)cyclohexanone
• 英文别名: (2S)-2-[(S)-(2-chloroanilino)-phenylmethyl]cyclohexan-1-one
• 化学式: C₁₉H₂₀ClNO
• 分子量: 313.827
• InChiKey: MSZDXSBDASSJMP-DNVCBOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  环己酮 、 苯甲醛 、 邻氯苯胺 在 氯化铵 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以92%的产率得到2-((2-chlorophenylamino)(phenyl)methyl)cyclohexanone
  参考文献：
  名称：

  氯化铵促进β-氨基酮的合成

  摘要：

  （2022 年）。氯化铵促进 β-氨基酮的合成。国际有机制剂和程序：卷。54，第 1 期，第 65-78 页。

  DOI：

  10.1080/00304948.2021.1994288

文献信息

• Nano-manganese hydrogen sulfate as a novel catalyst for the anti-diastereoselective Mannich reaction in water
  作者：H. Eshghi、M. Rahimizadeh、A. Javadian-Saraf、M. Hosseini

  DOI：10.1007/s11164-014-1587-8

  日期：2015.8

  obtained in high yields, with excellent diastereoselectivity, and short reaction time in the presence of a catalytic system comprising nano-Mn(HSO4)2 and a surfactant, for example sodium dodecyl sulfate. Use of mild, environmentally benign reaction conditions, low loading, and ready accessibility are the main features of this new catalyst. Graphical Abstract

  摘要 β-氨基羰基化合物是化学合成的诱人靶标，因为它们已广泛用作生物活性化合物，并且是多种药物的重要合成子。制备了纳米硫酸氢锰，并将其用作新型的有机转化纳米催化剂，即水中苯甲醛，苯胺和环己酮的曼尼希式反应。在包含纳米Mn（HSO 4）2和表面活性剂例如十二烷基硫酸钠的催化体系的存在下，以高收率，优异的非对映选择性和短反应时间获得曼尼希产物。使用温和的，对环境无害的反应条件，低载量和易于接近是这些新型催化剂的主要特征。 图形概要
• Synthesis and structure of the bimetallic organoantimony catalyst and its application in diastereoselective direct Mannich reaction as facile separation catalytic system
  作者：Niu Tang、Xingxing Song、Tianbao Yang、Renhua Qiu、Shuang-Feng Yin

  DOI：10.1016/j.jorganchem.2021.121820

  日期：2021.6

  A bimetallic organoantimony catalyst with four Lewis/Brønsted acidic/basic sites assembled orderly was successfully synthesized and showed high catalytic efficiency. It has been applied in diastereoselective direct Mannich reaction by adding 0.1 mol% catalyst. This reaction presented unexpected facile separation ability from homogenous solution to heterogeneous solution.

  成功合成了具有四个Lewis /Brønsted酸性/碱性位点的双金属有机锑催化剂，并显示出较高的催化效率。通过添加0.1摩尔％的催化剂，它已用于非对映选择性直接曼尼希反应中。该反应表现出出人意料的从均质溶液到异质溶液的容易的分离能力。
• Stereoselective Mannich reaction catalyzed by tetrahydroindolo[3,2-b]indole under solvent-free conditions
  作者：Jing Shi、Li-Zhu Zhang、Yong Pan、Deng-Qiang Feng、Guang-Yu Wu、Ke Yang、Xiao-Qiang Sun、Zheng-Yi Li

  DOI：10.1016/j.tetlet.2022.154128

  日期：2022.10

  have been designed and synthesized for the three-component direct Mannich reaction of aromatic aldehydes and aromatic amines with ketones. Significantly, the organocatalyst 2a delivered excellent catalytic stereoselectivity (up to >99:1) with good yields (up to 88 %) for above reaction process under the solvent-free conditions at room temperature. X-ray diffraction analysis reveals that organocatalyst

  一系列基于吲哚的有机催化剂（4b,9b-aryl-4b,5,9b,10-tetrahydroindolo[3,2- b ]indole 衍生物）（2a-2f）已被设计和合成用于三组分直接曼尼希芳香醛和芳香胺与酮的反应。值得注意的是，有机催化剂2a在室温和无溶剂条件下为上述反应过程提供了优异的催化立体选择性（高达 >99:1）和良好的收率（高达 88%）。X 射线衍射分析表明，有机催化剂2a具有八元中心环结构，具有有趣的应变四环连接性。2a中包含的特征刚性V形吲哚环结构并且2a和中间体之间形成的氢键相互作用优于抗立体选择性产物。
• Direct Mannich reaction mediated by Fe(Cp)2PF6 under solvent-free conditions
  作者：Rukhsana I. Kureshy、Santosh Agrawal、S. Saravanan、Noor-ul H. Khan、Arpan K. Shah、Sayed H.R. Abdi、Hari C. Bajaj、E. Suresh

  DOI：10.1016/j.tetlet.2009.11.022

  日期：2010.1

  Fe(Cp)(2)PF6 (5 mol %) efficiently catalyzed Mannich reaction of aldehydes, anilines, and ketones under solvent-free condition to give beta-amino-ketones in high yield (up to 94%) within 30 min with anti-isomer in excess. Simple experimental conditions and product isolation procedure makes this protocol potential for the development of clean and environment-friendly strategy for the synthesis of beta-amino-ketones. (C) 2009 Elsevier Ltd. All rights reserved.
• Ultrasound promoted efficient and green synthesis of β-amino carbonyl compounds in aqueous hydrotropic medium
  作者：Santosh Kamble、Arjun Kumbhar、Gajanan Rashinkar、Madhuri Barge、Rajashri Salunkhe

  DOI：10.1016/j.ultsonch.2011.12.001

  日期：2012.7

  Ultrasound promoted synthesis of beta-amino carbonyl compounds in aqueous hydrotropic medium at ambient temperature is reported. The remarkable features of the new procedure are shorter reaction time, excellent yields in aqueous medium, cleaner reaction profile and simple experimental and work-up procedure. (C) 2011 Elsevier B.V. All rights reserved.