2-[1'-(N-p-chlorophenylamino)-1'-(p-methoxyphenyl)]methylcyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[1'-(N-p-chlorophenylamino)-1'-(p-methoxyphenyl)]methylcyclohexanone
• 英文别名: 2-[(4-chloro-phenylamino)-(4-methoxy-phenyl)-methyl]-cyclohexanone；2-[(4-Chloroanilino)-(4-methoxyphenyl)methyl]cyclohexan-1-one
• 化学式: C₂₀H₂₂ClNO₂
• 分子量: 343.853
• InChiKey: VQLSMNVBMSPYDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 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：

  环己酮 、 对氯苯胺 、 4-甲氧基苯甲醛 在 Yb(OSO₂C₈H₁₇)3 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以84%的产率得到2-[1'-(N-p-chlorophenylamino)-1'-(p-methoxyphenyl)]methylcyclohexanone
  参考文献：
  名称：

  氟介质中稀土（III）全氟辛烷磺酸催化剂在氟双相体系中芳香醛，苯胺和甲基酮的曼尼希型反应

  摘要：

  稀土（III）全氟辛烷磺酸盐（RE（OPf）3）在氟介质中催化不同酮与各种芳香醛和芳香胺的三组分曼尼希型反应，以高收率得到各种β-芳基氨基酮。通过仅含催化剂的氟相的简单分离，反应可重复数次。

  DOI：

  10.1016/j.jfluchem.2006.07.009

文献信息

• Highly Efficient One-Pot Three-Component Mannich Reaction in Water Catalyzed by Heteropoly Acids
  作者：Najmodin Azizi、Lalleh Torkiyan、Mohammad R. Saidi

  DOI：10.1021/ol060498v

  日期：2006.5.1

  [reaction: see text] Heteropoly acids efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different amines in water at ambient temperature and afforded the corresponding beta-amino carbonyl compounds in good to excellent yields and with moderate diastereoselectivity. This method provides a novel and improved modification of the three-component

  [反应：参见文本]杂多酸可在环境温度下有效催化酮与芳香醛和不同胺在水中的一锅三组分曼尼希反应，并以良好或优异的收率和中等收率提供相应的β-氨基羰基化合物非对映选择性。该方法在温和的反应条件和干净的反应曲线方面，使用非常少量的催化剂和简单的后处理程序，就对三组分曼尼希反应进行了新颖和改进的改进。
• H5CoW12O40@nanosilica: a green, bifunctional, heterogeneous nanocatalyst for one-pot three-component Mannich reaction in water
  作者：Ezzat Rafiee、Masoud Kahrizi

  DOI：10.1007/s11164-013-1392-9

  日期：2015.5

  12-Tungestocobaltic acid, H5CoW12O40, was immobilized on nanosilica from rice husk ash to produce H5CoW12O40@nanosilica as a bifunctional nanocatalyst. The TEM result showed that the particles are mostly spherical in shape, and that they have an average size of approximately 10 nm. The catalytic activity of this catalyst was investigated in Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally diverse β-amino ketones in high to excellent yields. Short reaction time, simple work-up procedure, elimination of toxic solvents, and low catalyst loading are the advantages of this procedure.

  十二钨钴酸H5CoW12O40被固定在稻壳灰纳米硅上，制备出H5CoW12O40@纳米硅作为一种双功能纳米催化剂。透射电镜结果显示，这些粒子大多呈球形，平均尺寸约为10 nm。该催化剂在各种醛、酮和胺在水相中的Mannich反应中的催化活性得到了研究。这一快速过程以高至优异的产率提供了结构多样的β-氨基酮。短反应时间、简单的后处理步骤、消除有毒溶剂和低催化剂用量是这个方法的优点。
• One-pot, three-component Mannich-type reaction catalyzed by functionalized ionic liquid
  作者：Dong Fang、Kai Gong、Dai-zhen Zhang、Zu-liang Liu

  DOI：10.1007/s00706-009-0182-y

  日期：2009.11

  AbstractA three-component Mannich-type reaction of aromatic aldehydes, aromatic amines, and ketones was catalyzed by a novel functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) at room temperature to give various β-amino carbonyl compounds in good yields. The catalyst could be reused at least six times without noticeably reducing catalytic

  摘要新型功能化离子液体3-（N，N-二甲基十二烷基铵）丙烷磺酸硫酸氢盐（[DDPA] [HSO 4 ]）催化芳香醛，芳香胺和酮的三组分曼尼希型反应加热得到各种β-氨基羰基化合物。催化剂可以重复使用至少六次，而不会明显降低催化活性。 图形概要
• Brønsted acid-surfactant-combined catalyst for the Mannich reaction in water
  作者：Tao Chang、Leqin He、Li Bian、Haiyan Han、Mingxia Yuan、Xiaorui Gao

  DOI：10.1039/c3ra44726j

  日期：——

  A series of Brønsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N-dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity.

  研究人员合成了一系列用不同酸进行官能化的布氏酸-表面活性剂复合催化剂（BASCs），并将其用于催化醛、丙酮和胺在 25 °C 水中的三组分曼尼希反应。研究了离子液体的阳离子尾长和离子的影响以及催化剂的可回收性和 BASC 酸度 (H0)。结果表明，3-（N,N-二甲基辛基铵）丙磺酸甲苯硫酸盐（[DOPA][Tos]）的催化活性最好，因为在反应过程中会形成乳状液。催化过程简单，催化剂可通过简单的分离过程循环使用 9 次，而催化活性不会明显降低。
• Mesoporous silica nanoparticles (MSNs) as an efficient and reusable nanocatalyst for synthesis of β-amino ketones through one-pot three-component Mannich reactions
  作者：Zahra Nasresfahani、Mohammad Zaman Kassaee、Mohammad Nejati-Shendi、Esmaiel Eidi、Qazale Taheri

  DOI：10.1039/c6ra02454h

  日期：——

  Mesoporous silica nanoparticles (MSNs) proved efficient and reusable in the catalytic synthesis of β-amino ketones, through three-component Mannich reaction of ketones, aromatic aldehydes and aromatic amines under solvent-free conditions. Simple reaction conditions coupled with simple work-ups, makes this methodology a superior option for the synthesis of such β-amino ketones.

  在无溶剂条件下，通过酮，芳族醛和芳族胺的三组分曼尼希反应，介孔二氧化硅纳米粒子（MSNs）在催化合成β-氨基酮中被证明是有效且可重复使用的。简单的反应条件加上简单的后处理，使得该方法成为合成此类β-氨基酮的绝佳选择。