2-((2-methoxyphenylamino)(phenyl)methyl)cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((2-methoxyphenylamino)(phenyl)methyl)cyclohexanone
• 英文别名: (2S)-2-[(S)-(2-methoxyanilino)-phenylmethyl]cyclohexan-1-one
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: KPNMCFGMTFNXLT-OXQOHEQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-trichloroacetoxycyclohexene 、 N-phenylmethylene-2-methoxybenzeneamine 在 二丁基二甲氧基锡 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以63%的产率得到2-((2-methoxyphenylamino)(phenyl)methyl)cyclohexanone
  参考文献：
  名称：

  二甲基二丁基锡催化三烯基乙酸乙酸酯的曼尼希型反应

  摘要：

  通过使用二甲醇二丁基锡作为催化剂，可以实现三氯乙酸烯基酯与醛亚胺的新型曼尼希型反应，该反应可通过添加甲醇进行再生。醛，伯胺和烯基三氯乙酸酯的三组分偶联反应也已经有效地实现。这些程序可提供多种β氨基不仅从芳族醛也有来自α，β不饱和醛主要与酮的合成在高产率高达99％ -选择性。

  DOI：

  10.1002/adsc.200505156

文献信息

• 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。
• Highly Selective Synthesis of β-Amino Carbonyl Compounds over ZSM-5-SO₃H under Solvent-free Conditions
  作者：Ahmad Reza Massah、Roozbeh Javad Kalbasi、Neda Samah

  DOI：10.5012/bkcs.2011.32.5.1703

  日期：2011.5.20

  ZSM-5-$SO_3H$ efficiently catalyzed the one-pot three-component Mannich reaction of aldehydes, anilines, and ketones. $\beta}$-Aminocarbonyl compounds were obtained in reasonable yields and excellent stereoselectivities when the reaction was carried out at room temperature under solvent-free conditions. 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. The catalyst was recovered and reused for subsequent runs.

  ZSM-5-$SO_3H$可高效催化醛、苯胺和酮的一锅三组分曼尼希反应。$beta}$-氨基羰基化合物在室温无溶剂条件下进行反应时，产量合理，立体选择性极佳。简单的实验条件和产物分离步骤使该方法有望发展成清洁环保的$\beta}$-氨基酮合成策略。催化剂被回收并重复用于后续操作。
• 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.