4-((2-oxocyclohexyl)(phenylamino)methyl)benzonitrile | 1393116-43-2

• 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: 4-((2-oxocyclohexyl)(phenylamino)methyl)benzonitrile
• 英文别名: 4-((R)-((R)-2-oxocyclohexyl)(phenylamino)methyl)benzonitrile；4-[(R)-anilino-[(1R)-2-oxocyclohexyl]methyl]benzonitrile
• CAS: 1393116-43-2
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: YAKGXBGSSDHTOE-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己酮 、 苯胺 、 4-氰基苯甲醛 在 (11b'R)-4,4'-azanediylbis(2,6-di(naphthalen-1-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide) 作用下， 以 甲苯 为溶剂， 反应 12.5h， 以99%的产率得到4-((2-oxocyclohexyl)(phenylamino)methyl)benzonitrile
  参考文献：
  名称：

  Double axially chiral bisphosphorylimides as novel Brønsted acids in asymmetric three-component Mannich reaction

  摘要：

  A double axially chiral bisphosphorylimide has been demonstrated to be an efficient and highly sterically hindered Bronsted acid in asymmetric three-component Mannich reactions. Optically active syn-beta-amino ketones were obtained in high yields (up to 99%) with excellent diastereoselectivity (99:1) and enantioselectivity (up to 99% ee). A gram-scale reaction was also performed to prove the synthetic application value of this reaction. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.008

文献信息

• 二苯基四氢化双吲哚衍生物催化不对称 Mannich反应的应用
  申请人：常州大学

  公开号：CN108912000B

  公开（公告）日：2020-10-16

  本发明涉及化合物的新应用，特别涉及二苯基四氢化双吲哚衍生物作为不对称Mannich反应催化剂的应用，以芳胺、芳醛和环己酮为原料，二苯基四氢化双吲哚衍生物为催化剂进行Mannich催化反应。本发明的二苯基四氢化双吲哚衍生物合成工艺条件温和、催化效率高，其催化的不对称Mannich反应可获得很好的顺反比，具有广阔的应用前景。
• 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。
• 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.
• Double axially chiral bisphosphorylimides as novel Brønsted acids in asymmetric three-component Mannich reaction
  作者：Ying-Ying Chen、Yi-Jun Jiang、Yan-Sen Fan、Di Sha、Qifeng Wang、Guangliang Zhang、Liangyu Zheng、Suoqin Zhang

  DOI：10.1016/j.tetasy.2012.06.008

  日期：2012.6

  A double axially chiral bisphosphorylimide has been demonstrated to be an efficient and highly sterically hindered Bronsted acid in asymmetric three-component Mannich reactions. Optically active syn-beta-amino ketones were obtained in high yields (up to 99%) with excellent diastereoselectivity (99:1) and enantioselectivity (up to 99% ee). A gram-scale reaction was also performed to prove the synthetic application value of this reaction. (c) 2012 Elsevier Ltd. All rights reserved.