(S)-2-indan-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-indan-1-one
• 英文别名: (2S)-2-[(9-phenylfluoren-9-yl)amino]-2,3-dihydroinden-1-one
• 化学式: C₂₈H₂₁NO
• 分子量: 387.481
• InChiKey: GJMLPILYWCUYIS-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 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 正丁基锂 、 三甲基氯硅烷 、 lead(II) nitrate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 (S)-2-indan-1-one
  参考文献：
  名称：

  Synthesis of 2-[N-(9-phenylfluoren-9-yl)amino]-1-indanones by anionic cyclization of phenylalanine-derived oxazolidinones

  摘要：

  A novel preparation of N-(phenylfluorenyl)-2-amino-1-indanones is described. The key step is the cyclization of aryl-substituted o-bromophenylalanine-derived oxazolidinones with n-BuLi by halogen-metal exchange followed by in situ intramolecular acylation of the aryllithium intermediate. When this method was applied to an optically pure oxazolidinone derived from an amino acid, cyclization occurred with complete retention of the integrity of the chiral center.

  DOI：

  10.1021/jo00062a018

文献信息

• Paleo M. Rita, Castedo Luis, Dominguez Domingo, J. Org. Chem., 58 (1993) N 10, S 2763-2767
  作者：Paleo M. Rita, Castedo Luis, Dominguez Domingo

  DOI：——

  日期：——
• Synthesis of 2-[N-(9-phenylfluoren-9-yl)amino]-1-indanones by anionic cyclization of phenylalanine-derived oxazolidinones
  作者：M. Rita Paleo、Luis Castedo、Domingo Dominguez

  DOI：10.1021/jo00062a018

  日期：1993.5

  A novel preparation of N-(phenylfluorenyl)-2-amino-1-indanones is described. The key step is the cyclization of aryl-substituted o-bromophenylalanine-derived oxazolidinones with n-BuLi by halogen-metal exchange followed by in situ intramolecular acylation of the aryllithium intermediate. When this method was applied to an optically pure oxazolidinone derived from an amino acid, cyclization occurred with complete retention of the integrity of the chiral center.