1'-(4-(methoxycarbonyl)benzoyl)-6'-(N,N-dimethyl-amino)-1'H-spiro[fluorene-9,4'-indeno[1,2-b]pyrrole] | 1291063-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1'-(4-(methoxycarbonyl)benzoyl)-6'-(N,N-dimethyl-amino)-1'H-spiro[fluorene-9,4'-indeno[1,2-b]pyrrole]
• CAS: 1291063-52-9
• 化学式: C₃₄H₂₆N₂O₃
• 分子量: 510.592
• InChiKey: NSFDUSQWQPPRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6'-(N,N-dimethylamino)-1'H-spiro[fluorene-9,4'-indeno-[1,2-b]pyrrole] 、 1'-(4-(methoxycarbonyl)benzoyl)-6'-(N,N-dimethyl-amino)-1'H-spiro[fluorene-9,4'-indeno[1,2-b]pyrrole] 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 methyl 4-[(Z)-[6'-(dimethylamino)spiro[fluorene-9,4'-indeno[1,2-b]pyrrole]-2'-ylidene]-[6-(dimethylamino)spiro[1H-indeno[1,2-b]pyrrole-4,9'-fluorene]-2-yl]methyl]benzoate
  参考文献：
  名称：

  Near-infrared BODIPY dyes modulated with spirofluorene moieties

  摘要：

  New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1'H-spiro-[fluorene-9,4'-indeno[1,2-b] pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6'-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.073
• 作为产物：
  描述：

  9-(2-bromo-5-(dimethylamino)phenyl)-9H-fluoren-9-ol 在 aluminum (III) chloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 134.0h， 生成 1'-(4-(methoxycarbonyl)benzoyl)-6'-(N,N-dimethyl-amino)-1'H-spiro[fluorene-9,4'-indeno[1,2-b]pyrrole]
  参考文献：
  名称：

  Near-infrared BODIPY dyes modulated with spirofluorene moieties

  摘要：

  New structurally constrained BODIPY dyes having electron-donating substituents were synthesized. As the key compounds for the construction of the BODIPY dyes, 1'H-spiro-[fluorene-9,4'-indeno[1,2-b] pyrrole] (sp-FIP) derivatives with electron-donating groups, such as OMe and NMe2 at its 6'-position, were prepared using palladium-catalyzed intramolecular direct C-H arylation of a pyrrole moiety. The resulting BODIPY dyes showed bathochromic shift in absorption and fluorescence spectra in comparison to the unsubstituted analogs. Furthermore, pH-dependent reversible spectrum changes of the BODIPY dye were observed with the addition of trifluoroacetic acid (TFA) and subsequent addition of i-Pr2NEt. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.073