9H-fluoren-9-ylmethyl N-[(1S)-1-benzyl-2-(1-methyl-1H-pyrrol-2-yl)-2-oxoethyl]carbamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(1S)-1-benzyl-2-(1-methyl-1H-pyrrol-2-yl)-2-oxoethyl]carbamate
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-1-(1-methylpyrrol-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
• 化学式: C₂₉H₂₆N₂O₃
• 分子量: 450.537
• InChiKey: CTAXQDAITAVKOA-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-[(1S)-1-benzyl-2-benzotriazol-1-yl-2-oxoethyl]carbamate 、 N-甲基吡咯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以56%的产率得到9H-fluoren-9-ylmethyl N-[(1S)-1-benzyl-2-(1-methyl-1H-pyrrol-2-yl)-2-oxoethyl]carbamate
  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.