(R)-2-((R)-(phenylamino)(m-tolyl)methyl)cyclohexanone | 1393116-46-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-2-((R)-(phenylamino)(m-tolyl)methyl)cyclohexanone
• 英文别名: (2R)-2-[(R)-anilino-(3-methylphenyl)methyl]cyclohexan-1-one
• CAS: 1393116-46-5
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: LATAGHQWMYTNNM-ICSRJNTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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 、 苯胺 、 3-甲基苯甲醛 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96%的产率得到(R)-2-((R)-(phenylamino)(m-tolyl)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

• 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.