N-[(S)-1-(p-nitrophenyl)ethyl]-(S)-2-cyano-2-fluoro-p-tolylacetamide | 1036274-91-5

• 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: N-[(S)-1-(p-nitrophenyl)ethyl]-(S)-2-cyano-2-fluoro-p-tolylacetamide
• 英文别名: (2S)-2-cyano-2-fluoro-2-(4-methylphenyl)-N-[(1S)-1-(4-nitrophenyl)ethyl]acetamide
• CAS: 1036274-91-5
• 化学式: C₁₈H₁₆FN₃O₃
• 分子量: 341.342
• InChiKey: KYKSDXNODOJUBK-SCLBCKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-4-硝基-Alpha-甲基苄胺 、 (S)-α-cyano-α-fluoro-p-tolylacetyl chloride 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(S)-1-(p-nitrophenyl)ethyl]-(S)-2-cyano-2-fluoro-p-tolylacetamide
  参考文献：
  名称：

  Reliable assignment of absolute configuration of chiral amines based on the analysis of 1H NMR spectra of their CFTA amide diastereomers

  摘要：

  Applications of the CFTA method, a new and reliable procedure for the determination of the absolute configuration of chiral primary amines, are described in detail. In addition to the very high reactivity of CFTA chloride, the stable anti-periplanar conformers of CFTA amides, associated with the chiral structure of fluorine atom on a stereogenic center, are the key factors that make the technique of using H-1 NMR analysis of the CFTA diastereomers very reliable. In particular, this method is useful for the determination of the absolute stereochemistry of isotopically multi-labeled amino acid derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.003

文献信息

• Reliable assignment of absolute configuration of chiral amines based on the analysis of 1H NMR spectra of their CFTA amide diastereomers
  作者：Tomoya Fujiwara、Masaru Segawa、Hidehito Fujisawa、Taiki Murai、Tamiko Takahashi、Kenji Omata、Kuninobu Kabuto、Siegfried N. Lodwig、Clifford J. Unkefer、Yoshio Takeuchi

  DOI：10.1016/j.tetasy.2008.03.003

  日期：2008.4

  Applications of the CFTA method, a new and reliable procedure for the determination of the absolute configuration of chiral primary amines, are described in detail. In addition to the very high reactivity of CFTA chloride, the stable anti-periplanar conformers of CFTA amides, associated with the chiral structure of fluorine atom on a stereogenic center, are the key factors that make the technique of using H-1 NMR analysis of the CFTA diastereomers very reliable. In particular, this method is useful for the determination of the absolute stereochemistry of isotopically multi-labeled amino acid derivatives. (C) 2008 Elsevier Ltd. All rights reserved.