2,2,2-trifluoro-N-[(2S)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2,2,2-trifluoro-N-[(2S)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetamide
• 英文别名: (S)-2,2,2-trifluoro-N-(1-oxo-2,3-dihydro-1H-inden-2-yl)acetamide；2,2,2-trifluoro-N-[(2S)-3-oxo-1,2-dihydroinden-2-yl]acetamide
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: VPLURSABVWRHNR-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 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 三氯化铝 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,2,2-trifluoro-N-[(2S)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetamide
  参考文献：
  名称：

  N-Tfa- and N-Fmoc-(α-aminoacyl)benzotriazoles as Chiral C-Acylating Reagents under Friedel−Crafts Reaction Conditions

  摘要：

  Chiral N-Tfa- and N-Fmoc-protected (alpha-aminoacyl)benzotriazoles 1a-j undergo Friedel-Crafts-type reactions with indole, N-methylindole, pyrrole, N-methylpyrrole, and benzene in the presence of AlCl3 in efficient two-step sequences leading to enantiomerically pure alpha-amino N-heterocyclic ketones 2, 3, 5, 6, and 7 or diketone 4. In the absence of a reactive partner, Phe- and Trp-derivatives la, Id undergo intramolecular cyclization to afford 12 and 13, again with retention of chirality.

  DOI：

  10.1021/jo050226q

文献信息

• <i>N</i>-Tfa- and <i>N</i>-Fmoc-(α-aminoacyl)benzotriazoles as Chiral <i>C</i>-Acylating Reagents under Friedel−Crafts Reaction Conditions
  作者：Alan R. Katritzky、Rong Jiang、Kazuyuki Suzuki

  DOI：10.1021/jo050226q

  日期：2005.6.1

  Chiral N-Tfa- and N-Fmoc-protected (alpha-aminoacyl)benzotriazoles 1a-j undergo Friedel-Crafts-type reactions with indole, N-methylindole, pyrrole, N-methylpyrrole, and benzene in the presence of AlCl3 in efficient two-step sequences leading to enantiomerically pure alpha-amino N-heterocyclic ketones 2, 3, 5, 6, and 7 or diketone 4. In the absence of a reactive partner, Phe- and Trp-derivatives la, Id undergo intramolecular cyclization to afford 12 and 13, again with retention of chirality.
• 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.