2-((2-fluorophenyl)(phenylamino)methyl)cyclohexanone | 1393116-32-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-((2-fluorophenyl)(phenylamino)methyl)cyclohexanone
• 英文别名: (R)-2-((R)-(2-fluorophenyl)(phenylamino)methyl)cyclohexanone；(2R)-2-[(R)-anilino-(2-fluorophenyl)methyl]cyclohexan-1-one
• CAS: 1393116-32-9
• 化学式: C₁₉H₂₀FNO
• 分子量: 297.372
• InChiKey: NAHSCJPRFXUWRR-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  3

反应信息

• 作为产物：
  描述：

  环己酮 、 2-氟苯甲醛 、 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87%的产率得到2-((2-fluorophenyl)(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

• 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。
• 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.