(3S)-5-methyl-3-[N-(9'-phenylfluoren-9'-yl)amino]hexan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (3S)-5-methyl-3-[N-(9'-phenylfluoren-9'-yl)amino]hexan-2-one
• 英文别名: (3S)-5-methyl-3-[(9-phenylfluoren-9-yl)amino]hexan-2-one
• 化学式: C₂₆H₂₇NO
• 分子量: 369.506
• InChiKey: FDGVTAAOCBBHTQ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-溴-9-苯基芴 在 lithium hydroxide 、 potassium phosphate 、 lead(II) nitrate 、 对甲苯磺酸 、 溶剂黄146 、 甲酸乙酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 113.0h， 生成 (3S)-5-methyl-3-[N-(9'-phenylfluoren-9'-yl)amino]hexan-2-one
  参考文献：
  名称：

  Enantiospecific Synthesis of N-(9-Phenylfluoren-9-yl)-α-amino Ketones

  摘要：

  Enantiomerically pure N-(9-phenylfluoren-9-yl)-alpha-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-alpha-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-alpha-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-beta-amino alcohols depending upon the nature of the reducing agent.

  DOI：

  10.1021/jo9707646

文献信息

• Enantiospecific Synthesis of <i>N</i>-(9-Phenylfluoren-9-yl)-α-amino Ketones
  作者：M. Rita Paleo、M. Isabel Calaza、F. Javier Sardina

  DOI：10.1021/jo9707646

  日期：1997.10.1

  Enantiomerically pure N-(9-phenylfluoren-9-yl)-alpha-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-alpha-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-alpha-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-beta-amino alcohols depending upon the nature of the reducing agent.