2-((4-bromophenyl)(phenylamino)methyl)cyclohexanone | 1393116-41-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((4-bromophenyl)(phenylamino)methyl)cyclohexanone
• 英文别名: (R)-2-((R)-(4-bromophenyl)(phenylamino)methyl)cyclohexanone；(2R)-2-[(R)-anilino-(4-bromophenyl)methyl]cyclohexan-1-one
• CAS: 1393116-41-0
• 化学式: C₁₉H₂₀BrNO
• 分子量: 358.278
• InChiKey: VOKIAFSHJMXQRT-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己酮 、 对溴苯甲醛 、 苯胺 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92%的产率得到2-((4-bromophenyl)(phenylamino)methyl)cyclohexanone
  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

• IsosteviolProline Conjugates as Highly Efficient Amphiphilic Organocatalysts for Asymmetric Three-Component Mannich Reactions in the Presence of Water
  作者：Ya-Jie An、Chuan-Chuan Wang、Zi-Ping Liu、Jing-Chao Tao

  DOI：10.1002/hlca.201100265

  日期：2012.1

  work, six isosteviolamino acid conjugates were designed and synthesized through simple condensation on a large scale without protecting group (Scheme). These amphiphilic organocatalysts mediated asymmetric three‐component Mannich reactions of cyclohexanone and anilines with aromatic aldehydes in the presence of H2O. Meanwhile, the isosteviolproline conjugate 3b has been established as a highly efficient

  在这项工作中，设计并通过简单的大规模缩合反应合成了六种异戊四醇氨基酸共轭基，没有保护基（方案）。这些两亲性有机催化剂在H 2 O存在下介导的环己酮和苯胺与芳族醛的不对称三组分曼尼希反应。同时，异雌醇脯氨酸共轭物3b已被确立为高效催化剂（表1），并提供了合成反应。曼尼希（Mannich）产品具有出色的非对映选择性（顺/反高达98：2）和对映选择性（高达> 99％ee）；表3）。提出了在H 2 O存在下反应的过渡态（图2）。
• 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.