(S)-2,2,2-trifluoro-N-(1-(1-methyl-1H-pyrrol-3-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

• 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: (S)-2,2,2-trifluoro-N-(1-(1-methyl-1H-pyrrol-3-yl)-1-oxo-3-phenylpropan-2-yl)acetamide
• 英文别名: TFA-L-Phe-(3-(N-Me)Pyr)；2,2,2-trifluoro-N-[(2S)-1-(1-methylpyrrol-3-yl)-1-oxo-3-phenylpropan-2-yl]acetamide
• 化学式: C₁₆H₁₅F₃N₂O₂
• 分子量: 324.303
• InChiKey: LFKPVDXJWMLFKA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-trifluoroacetyl-L-phenylalanine 在 aluminum (III) chloride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 (S)-2,2,2-trifluoro-N-(1-(1-methyl-1H-pyrrol-2-yl)-1-oxo-3-phenylpropan-2-yl)acetamide 、 (S)-2,2,2-trifluoro-N-(1-(1-methyl-1H-pyrrol-3-yl)-1-oxo-3-phenylpropan-2-yl)acetamide
  参考文献：
  名称：

  TFA 保护的 α-氨基酸 N-羟基琥珀酰亚胺酯：分子间和分子内酰化的应用

  摘要：

  The utilization of N-trifluoroacetyl (TFA)-alpha-amino acid N-hydroxysuccinimide ester (OSu) derivatives, a promising acylating agent with high storage stability, is reported for Friedel Crafts acylation into arenes and N-heterocycles. The reaction between TFA-Phe-OSu derivatives and arenes afforded inter- and intramolecular products. TFA-Tyr-OSu derivatives, which possess hydroxyl substituent in the aromatic moiety of phenylalanine, afforded only intermolecular product with benzene. The heterocyclic TFA-Pro-OSu also shows relatively high reactivity toward acylation.

  DOI：

  10.3987/com-18-s(t)65

文献信息

• TFA-Protected α-Amino Acid N-Hydroxysuccinimide Ester: Application for Inter- and Intramolecular Acylation
  作者：Makoto Hashimoto、Zetryana Puteri Tachrim、Kazuhiro Oida、Fumina Ohashi、Haruna Wakasa、Haruka Ikemoto、Natsumi Kurokawa、Yasuko Sakihama、Yasuyuki Hashidoko、Takeyuki Suzuki

  DOI：10.3987/com-18-s(t)65

  日期：——

  The utilization of N-trifluoroacetyl (TFA)-alpha-amino acid N-hydroxysuccinimide ester (OSu) derivatives, a promising acylating agent with high storage stability, is reported for Friedel Crafts acylation into arenes and N-heterocycles. The reaction between TFA-Phe-OSu derivatives and arenes afforded inter- and intramolecular products. TFA-Tyr-OSu derivatives, which possess hydroxyl substituent in the aromatic moiety of phenylalanine, afforded only intermolecular product with benzene. The heterocyclic TFA-Pro-OSu also shows relatively high reactivity toward acylation.