(R,R,R)-N-camphorsulfonyl-diphenylethylene diamine | 676270-67-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R,R,R)-N-camphorsulfonyl-diphenylethylene diamine
• 英文别名: (1R,4S)-N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonamide；N-[(1R,2R)-2-amino-1,2-diphenylethyl]-1-[(1R,4S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 676270-67-0
• 化学式: C₂₄H₃₀N₂O₃S
• 分子量: 426.58
• InChiKey: ITNLZZDQOMWQDT-BQUSRXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  左旋樟脑磺酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (R,R,R)-N-camphorsulfonyl-diphenylethylene diamine
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017
• 作为试剂：
  描述：

  2-溴-4'-硝基苯乙酮 在 [RhCl2(p-cymene)]2 、 (R,R,R)-N-camphorsulfonyl-diphenylethylene diamine 、 sodium formate 、 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 反应 8.0h， 以88%的产率得到(S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017