2-[1'-(N-p-methoxyphenylamino)-1'-phenyl]methylcyclohexanone | 21854-76-2

• 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-methoxyphenylamino)-1'-phenyl]methylcyclohexanone
• 英文别名: 2-[(4-Methoxyanilino)-phenylmethyl]cyclohexan-1-one
• CAS: 21854-76-2
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: JKSMDLYVYYTTQR-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±25.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  2-[1'-(N-p-methoxyphenylamino)-1'-phenyl]methylcyclohexanone 在 tris-(dibenzylideneacetone)dipalladium(0) 、 dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 (6S,6aS)-5-(4-methoxyphenyl)-6-phenyl-5,6,6a,7,8,9-hexahydrophenanthridine
  参考文献：
  名称：

  Tosylhydrazide-Promoted Palladium-Catalyzed Reaction of β-Aminoketones witho-Dihaloarenes: Combining Organocatalysis and Transition-Metal Catalysis

  摘要：

  DOI：

  10.1002/anie.201006996
• 作为产物：
  描述：

  1-环己烯氧基三甲基硅烷 、 4-methoxy-N-[(E)-phenylmethylidene]aniline 在 1-乙基-3-甲基咪唑三氟甲磺酸盐 作用下， 反应 14.0h， 以91%的产率得到2-[1'-(N-p-methoxyphenylamino)-1'-phenyl]methylcyclohexanone
  参考文献：
  名称：

  离子液体促进曼尼希型反应

  摘要：

  甲硅烷基烯醇化物与醛亚胺的曼尼希型反应以 [emim] OTf 作为溶剂顺利进行，无需添加活化剂，以优异的产率提供对氨基羰基化合物。

  DOI：

  10.1055/s-2005-864816

文献信息

• Enantioselective Direct <i>anti</i>-Selective Mannich-type Reactions Catalyzed by 3-Pyrrolidinecarboxylic Acid in the Presence of Potassium Carbonate: Addition of Potassium Carbonate Improves Enantioselectivities
  作者：Yuvraj Garg、Fujie Tanaka

  DOI：10.1021/acs.orglett.0c01561

  日期：2020.6.5

  Mannich-type reactions of cyclohexanone and related six-membered-ring ketones with N-p-methoxyphenyl-protected imines of arylaldehydes catalyzed by 3-pyrrolidinecarboxylic acid in the presence of K2CO3 that afford anti-isomers of the Mannich products with high diastereo- and enantioselectivities are reported. Addition of K2CO3 improved the enantioselectivities of the reactions catalyzed by 3-pyrrolidinecarboxylic

  环己酮的曼尼希型反应和相关的六元环酮与ñ - p 3吡咯烷羧酸于K的存在下催化的芳醛的甲氧基苯基保护的亚胺2 CO 3的是得到抗曼尼希产品具有高的异构体报告了非对映选择性和对映选择性。K 2 CO 3的添加改善了由3-吡咯烷羧酸催化的反应的对映选择性，同时保留了反应的抗选择性。因此，使用K 2 CO 3 扩展了这些有机催化反应的范围，以提供具有高对映选择性的产物。
• Heteropoly acid in ionic liquid — An efficient and recyclable system for one-pot three-component Mannich reaction
  作者：Meghana S Rasalkar、Sachin V Bhilare、Amol R Deorukhkar、Nitin B Darvatkar、Manikrao M Salunkhe

  DOI：10.1139/v06-176

  日期：2007.1.1

  This paper describes a one-pot three-component Mannich reaction, catalyzed by phosphotungstic acid (H3PW12O40), a heteropoly acid in ionic liquid. The catalyst was found to be mild and efficient, and the protocol affords β-amino ketones in good yields under ambient conditions. Several ionic liquids and conventional organic solvents were employed for the reaction. The ionic liquid 1-butyl-3-methylimidazolium

  本文描述了一种由离子液体中的杂多酸磷钨酸 (H3PW12O40) 催化的一锅三组分曼尼希反应。发现该催化剂温和且高效，并且该方案在环境条件下以良好的产率提供 β-氨基酮。该反应使用了几种离子液体和常规有机溶剂。离子液体 1-丁基-3-甲基咪唑鎓四氟硼酸盐 ([bmim]BF4) 在产物产率方面提供了最好的结果。观察到均相反应介质有利于反应的产率。关键词：曼尼希反应，β-氨基酮，磷钨酸，离子液体，可回收性。
• 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。
• Modification of poly(vinyl chloride) with pendant metal complex for catalytic applications
  作者：Gopalakrishnapanicker Rajesh Krishnan、Modiyuzhathil K. Sreeraj、Krishnapillai Sreekumar

  DOI：10.1016/j.crci.2013.03.013

  日期：2013.8

  Résumé Poly(vinyl chloride) was modified to develop an alternative support for the preparation of polymer-supported catalysts. Commercially available poly(vinyl chloride) was synthetically modified to a polymer containing pendant primary amino groups. The Schiff-base of salicylaldehyde and the amino polymer were prepared and were used as the ligands in the synthesis of a polymer-supported copper complex. The polymer-supported ligand and catalysts were characterized by various physical methods. The polymer with the pendant copper complex was able to catalyze the one-pot three-component Mannich reaction between aldehydes, ketones and anilines under mild and environmentally friendly conditions. The catalyst can be recovered by simple filtration and is reusable. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  摘要 对聚（氯乙烯）进行改性，以开发制备聚合物支撑催化剂的替代支撑物。将市售的聚氯乙烯合成改性为含有伯氨基的聚合物。制备出水杨醛希夫碱和氨基聚合物，并将其作为配体用于合成聚合物支撑的铜络合物。通过各种物理方法对聚合物支撑配体和催化剂进行了表征。带有铜络合物的聚合物能够在温和、环保的条件下催化醛、酮和苯胺之间的一锅三组分曼尼希反应。催化剂可通过简单过滤回收，并可重复使用。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.docx
• Tanaka, Nobuyuki; Masaki, Yukio, Synlett, 2000, # 3, p. 406 - 408
  作者：Tanaka, Nobuyuki、Masaki, Yukio

  DOI：——

  日期：——