6-[(9-Phenylfluoren-9-yl)amino]-5,6-dihydrocyclopenta[f][1,3]benzodioxol-7-one | 195193-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-[(9-Phenylfluoren-9-yl)amino]-5,6-dihydrocyclopenta[f][1,3]benzodioxol-7-one
• CAS: 195193-47-6
• 化学式: C₂₉H₂₁NO₃
• 分子量: 431.491
• InChiKey: LOLDZRXAODTGJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[(9-Phenylfluoren-9-yl)amino]-5,6-dihydrocyclopenta[f][1,3]benzodioxol-7-one 、 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以7%的产率得到
  参考文献：
  名称：

  The first total synthesis of (±)-ribasine

  摘要：

  The first total synthesis of (+/-)-ribasine was achieved by stereocontrolled addition of 3,4-methylenedioxy-substituted alpha-lithium-o-toluate 13c to 2-(9-phenylfluoren-9-yl)-amino-1-indanone 5. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10778-x
• 作为产物：
  描述：

  3-(9-phenylfluoren-9-yl)-4-<<2-bromo-4,5-(methylenedioxy)phenyl>methyl>oxazolidin-5-one 在 正丁基锂 、 溶剂黄146 作用下， 生成 6-[(9-Phenylfluoren-9-yl)amino]-5,6-dihydrocyclopenta[f][1,3]benzodioxol-7-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.
• The first total synthesis of (±)-ribasine
  作者：Lourdes Ollero、Luis Castedo、Domingo Domínguez

  DOI：10.1016/s0040-4039(97)10778-x

  日期：1998.3

  The first total synthesis of (+/-)-ribasine was achieved by stereocontrolled addition of 3,4-methylenedioxy-substituted alpha-lithium-o-toluate 13c to 2-(9-phenylfluoren-9-yl)-amino-1-indanone 5. (C) 1998 Elsevier Science Ltd. All rights reserved.