(R)-2,2-ditrifluoromethyl-N-(2,2-difluoro-1-phenylethyl)propanamide | 1246282-61-0

• 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: (R)-2,2-ditrifluoromethyl-N-(2,2-difluoro-1-phenylethyl)propanamide
• 英文别名: N-[(1R)-2,2-difluoro-1-phenylethyl]-3,3,3-trifluoro-2-methyl-2-(trifluoromethyl)propanamide
• CAS: 1246282-61-0
• 化学式: C₁₃H₁₁F₈NO
• 分子量: 349.224
• InChiKey: PLQVGNRIBAYASC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (R)-2,2-difluoro-1-phenylethylamine 、 2,2-双(三氟甲基)丙酸 在 N-甲基咪唑 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(R)-2,2-ditrifluoromethyl-N-(2,2-difluoro-1-phenylethyl)propanamide
  参考文献：
  名称：

  Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications

  摘要：

  The preliminary results presented in this work show that an enantiomer purification approach based on SDE via sublimation can be extended to non-volatile liquid compounds such as alpha-(phenyl)ethylamine and its beta-fluoro-derivatives by way of their rational modification with a sublimation enabling tag. 3,3,3-Trifluoro-2-(trifluoromethyl)-2-methyl-propanoic acid was found to perfectly serve the role of such a modifying tag. Thus, the corresponding amides derived from the amines and the fluorinated propanoic acid were highly crystalline and reasonably volatile compounds allowing for their sublimation at room temperature under normal pressure. All of these derivatives showed substantial self-disproportionation of enantiomers (SDEs) via sublimation under kinetic conditions (on a Petri dish in the open air). These preliminary results serve as a proof of a new principle that may extend the generality of enantiomer purification via sublimation to various organic compounds with physico-chemical properties of which render them otherwise unsuitable for a sublimation procedure. In particular, the very attractive cost structure of sublimation procedure renders this approach of potentially high practical and economic efficiency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.040

文献信息

• Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications
  作者：Hisanori Ueki、Manabu Yasumoto、Vadim A. Soloshonok

  DOI：10.1016/j.tetasy.2010.04.040

  日期：2010.6

  The preliminary results presented in this work show that an enantiomer purification approach based on SDE via sublimation can be extended to non-volatile liquid compounds such as alpha-(phenyl)ethylamine and its beta-fluoro-derivatives by way of their rational modification with a sublimation enabling tag. 3,3,3-Trifluoro-2-(trifluoromethyl)-2-methyl-propanoic acid was found to perfectly serve the role of such a modifying tag. Thus, the corresponding amides derived from the amines and the fluorinated propanoic acid were highly crystalline and reasonably volatile compounds allowing for their sublimation at room temperature under normal pressure. All of these derivatives showed substantial self-disproportionation of enantiomers (SDEs) via sublimation under kinetic conditions (on a Petri dish in the open air). These preliminary results serve as a proof of a new principle that may extend the generality of enantiomer purification via sublimation to various organic compounds with physico-chemical properties of which render them otherwise unsuitable for a sublimation procedure. In particular, the very attractive cost structure of sublimation procedure renders this approach of potentially high practical and economic efficiency. (C) 2010 Elsevier Ltd. All rights reserved.