2-[Anilino-[4-(trifluoromethyl)phenyl]methyl]cyclohexan-1-one | 1195787-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[Anilino-[4-(trifluoromethyl)phenyl]methyl]cyclohexan-1-one
• CAS: 1195787-68-8
• 化学式: C₂₀H₂₀F₃NO
• 分子量: 347.38
• InChiKey: USHOOBIRWBPDNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 环己酮 、 苯胺 在 (11-Cyclohexyl-10,12-dihydrobenzo[b][5,1]benzazabismocin-5-yl) 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate 作用下， 以 水 为溶剂， 反应 12.0h， 以95%的产率得到2-[Anilino-[4-(trifluoromethyl)phenyl]methyl]cyclohexan-1-one
  参考文献：
  名称：

  Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water

  摘要：

  An air-stable hypervalent organobismuth (III) perfluorooctanesulfonate was synthesized and characterized by spectroscopic and X-ray crystallographic techniques, and found to exhibit high catalytic efficiency towards one-pot Mannich-type reaction of ketones with aromatic aldehydes and aromatic amines in water. This catalyst also shows good recyclability and reusability. This catalytic system would provide a simple, efficient and 'green' avenue towards the synthesis of beta-amino ketones. (C) 2009 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2009.07.018

文献信息

• Direct Asymmetric Mannich Reaction Catalyzed by a d-Glucosamine-Derived Organocatalyst
  作者：Rama Peddinti、Arun Sharma

  DOI：10.1055/s-0036-1591740

  日期：2018.3

  Sugar-based primary amines have been employed as organocatalysts for the direct asymmetric Mannich reaction. By catalyst-screening experiments, we observed that catalysts bearing a hydroxy function at C-3 actively participated in the reaction, possibly through hydrogen bonding with the imine generated in situ, to provide β-amino carbonyl compounds with better diastereoselectivity and enantioselectivity

  糖基伯胺已被用作直接不对称曼尼希反应的有机催化剂。通过催化剂筛选实验，我们观察到在 C-3 处带有羟基官能团的催化剂积极参与反应，可能是通过与原位生成的亚胺形成氢键，从而提供具有更好非对映选择性和对映选择性的 β-氨基羰基化合物。获得的所有产品都处于良好至极好的对映体过量。
• 2-Pyrrolidinecarboxylic Acid Ionic Liquid as a Highly Efficient Organocatalyst for the Asymmetric One-Pot Mannich Reaction
  作者：Xin Zheng、Yun-Bo Qian、Yongmei Wang

  DOI：10.1002/ejoc.200901088

  日期：2010.1

  A novel one-pot three-component asymmetric Mannich reaction using [EMIm][Pro] (1) as a catalyst has been developed. By employing this new reaction system, a variety of optically active β-amino carbonyl compounds were synthesized in up to 99 % yield with up to >99 dr and >99 % ee. The reaction conditions have been optimized and the mechanism for the asymmetric induction is discussed.

  已经开发了一种使用 [EMIm][Pro] (1) 作为催化剂的新型一锅三组分不对称曼尼希反应。通过采用这种新的反应系统，合成了多种光学活性 β-氨基羰基化合物，产率高达 99%，高达 >99 dr 和 >99% ee。优化了反应条件并讨论了不对称诱导的机制。
• Direct Asymmetric Three-Component Mannich Reaction Catalyzed by Chiral Counteranion-Assisted Silver
  作者：Zhongyou Yin、Jianxin Guo、Rui Zhang、Xiaoyun Hu、Victor Borovkov

  DOI：10.1021/acs.joc.0c00031

  日期：2020.8.21

  Direct asymmetric three-component Mannich reaction involving simple ketones (such as cyclohexanone, acetone, and acetophenone) as donors and catalyzing by silver tartaric acid-derived phosphate was realized to afford a series of optically active β-amino-ketone derivatives in high yields (up to 96%) and good-to-high enantioselectivities (up to 97%) with moderate-to-good diastereoselectivities. This

  实现了以简单的酮（例如环己酮，丙酮和苯乙酮）为供体并由酒石酸银衍生的磷酸酯催化的直接不对称三组分曼尼希反应，可高产率提供一系列光学活性的β-氨基酮衍生物（高达96％）和良好到高的对映选择性（高达97％）以及中等到良好的非对映选择性。这是通过手性抗衡阴离子定向策略直接催化不对称三组分曼尼希反应的第一个例子。
• Chiral Brønsted Acid-Catalyzed Direct Asymmetric Mannich Reaction
  作者：Qi-Xiang Guo、Hua Liu、Chang Guo、Shi-Wei Luo、Yi Gu、Liu-Zhu Gong

  DOI：10.1021/ja068236b

  日期：2007.4.1

  A chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction has been described. Various phosphoric acids, prepared from BINOL and H-8-BINOL derivatives, have been evaluated for catalyzing the direct Mannich reaction. In the presence of a truly catalytic amount of the phosphoric acid, anti-selective Mannich reactions of cyclic ketones with a wide scope of aldimines were obtained in high yields with excellent enantioselectivities (up to 98% ee) and high diastereomeric ratios (up to 98/2 dr). A one-pot Mannich reaction using aromatic ketones as donors proceeded smoothly to give beta-amino carbonyls with fairly good enantioselectivities.
• Enzyme-catalyzed asymmetric Mannich reaction using acylase from Aspergillus melleus
  作者：Zhi Guan、Jian Song、Yang Xue、Da-Cheng Yang、Yan-Hong He

  DOI：10.1016/j.molcatb.2014.11.007

  日期：2015.1

  Acylase I from Aspergillus melleus (AMA) displayed catalytic promiscuity towards one-pot asymmetric Mannich reaction in acetonitrile for the first time. AMA showed favourable catalytic activity with good adaptability to different substrates. The activity and stereoselectivity of the enzyme could be improved by adjusting solvent, pH, water content, temperature, molar ratio of substrates and enzyme loading. The enantioselectivities up to 89% ee, diastereoselectivities up to 90:10 dr (syn/anti) and yields up to 82% were achieved. This work offered a novel case of enzyme catalytic promiscuity and a potential synthetic method for organic chemistry. (C) 2014 Elsevier B.V. All rights reserved.