2--3-<2-bromo-4,5-(methylenedioxy)phenyl>propanoic acid | 147912-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2--3-<2-bromo-4,5-(methylenedioxy)phenyl>propanoic acid
• 英文别名: 2--3-<2-bromo-4,5-(methylenedioxy)phenyl>propanoate；3-(6-Bromo-1,3-benzodioxol-5-yl)-2-[(9-phenylfluoren-9-yl)amino]propanoic acid
• CAS: 147912-69-4
• 化学式: C₂₉H₂₂BrNO₄
• 分子量: 528.402
• InChiKey: JIJGPSGQOFZKDO-UHFFFAOYSA-N

物化性质

• 沸点：
  672.7±55.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2--3-<2-bromo-4,5-(methylenedioxy)phenyl>propanoic acid 在 正丁基锂 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.5h， 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
• 作为产物：
  描述：

  9-溴-9-苯基芴 在 lithium hydroxide 、 lead(II) nitrate 、 benzyltrimethylammonium tribromide 、 三乙胺 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 2--3-<2-bromo-4,5-(methylenedioxy)phenyl>propanoic acid
  参考文献：
  名称：

  Enantiospecific synthesis of (+)-ribasine

  摘要：

  The alkaloid (+)-ribasine was synthesized by stereocontrolled addition of substituted alpha-lithium-o-toluate 6d to enantiomerically pure (R)-N-(9-phenylfluoren-9-yl)-2-amino-5,6-(methylenedioxy)indan-1-one [(+)-5]. Aminoindanone (+)-5 was prepared from amino acid (-)-15 obtained by diastereoselective alkylation of a chiral glycine enolate synthon. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00133-7

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：——
• Enantiospecific synthesis of (+)-ribasine
  作者：Lourdes Ollero、Luis Castedo、Domingo Domínguez

  DOI：10.1016/s0040-4020(99)00133-7

  日期：1999.4

  The alkaloid (+)-ribasine was synthesized by stereocontrolled addition of substituted alpha-lithium-o-toluate 6d to enantiomerically pure (R)-N-(9-phenylfluoren-9-yl)-2-amino-5,6-(methylenedioxy)indan-1-one [(+)-5]. Aminoindanone (+)-5 was prepared from amino acid (-)-15 obtained by diastereoselective alkylation of a chiral glycine enolate synthon. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.