1-phenyl-4,7-dihydro-4,7-ethano-2H-isoindole | 1303477-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-phenyl-4,7-dihydro-4,7-ethano-2H-isoindole
• 英文别名: 3-Phenyl-4-azatricyclo[5.2.2.02,6]undeca-2,5,8-triene；3-phenyl-4-azatricyclo[5.2.2.02,6]undeca-2,5,8-triene
• CAS: 1303477-70-4
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: WQNQYJSUGCOPLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-phenyl-4,7-dihydro-4,7-ethano-2H-isoindole 在 三氟化硼乙醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of π-expanded O-chelated boron–dipyrromethene as an NIR dye

  摘要：

  A pi-expanded BODIPY dye with an intramolecular boronate skeleton was synthesized by retro Diets-Alder reaction of the bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY and the subsequent O-chelation. The photophysical and electrochemical properties were examined by UV-vis, fluorescence, CV measurements, and DFT calculation. This BODIPY exhibited the absorption and emission over a visible-NIR region at 600-850 nm. O-chelated BODIPY showed a bathocromic shift compared to F-BODIPYs. This dye showed a bright fluorescence emission at 733 nm with the high phi value of 0.58. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.016
• 作为产物：
  描述：

  2-(tert-butyl) 1-ethyl 3-iodo-4,7-dihydro-2H-4,7-ethanoisoindole-1,2-dicarboxylate 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium hydroxide 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1-phenyl-4,7-dihydro-4,7-ethano-2H-isoindole
  参考文献：
  名称：

  Synthesis of π-expanded O-chelated boron–dipyrromethene as an NIR dye

  摘要：

  A pi-expanded BODIPY dye with an intramolecular boronate skeleton was synthesized by retro Diets-Alder reaction of the bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY and the subsequent O-chelation. The photophysical and electrochemical properties were examined by UV-vis, fluorescence, CV measurements, and DFT calculation. This BODIPY exhibited the absorption and emission over a visible-NIR region at 600-850 nm. O-chelated BODIPY showed a bathocromic shift compared to F-BODIPYs. This dye showed a bright fluorescence emission at 733 nm with the high phi value of 0.58. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.016

文献信息

• Synthesis of π-conjugated asymmetric aza-BODIPYs via nitrosobicyclopyrroles
  作者：Ryota Mori、Minenari Asakura、Yukinori Kobayashi、Hiromu Mashimo、Makoto Roppongi、Satoshi Ito

  DOI：10.1016/j.tetlet.2022.153759

  日期：2022.4

  π-Conjugated aza-BODIPYs with absorption in the near-infrared region have attracted attention, but there are few reports of their synthesis. We report the synthesis and absorption properties of π-conjugated asymmetric aza-BODIPYs by nitrosation and retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused bicyclopyrroles. We also synthesized aza-BODIPY fused with [2.3]naphtho and [2.3]anthra structures

  在近红外区域具有吸收的π-共轭氮杂-BODIPYs引起了人们的关注，但对其合成的报道很少。我们报告了通过双环[2.2.2]辛二烯稠合双环吡咯的亚硝化和逆-Diels-Alder 反应合成π-共轭不对称氮杂-BODIPYs 的性质和吸收性能。我们还首次通过该方法合成了融合[2.3]萘和[2.3]蒽结构的aza-BODIPY和π-共轭氮杂-O-螯合物BODIPY。
• Synthesis of π-expanded O-chelated boron–dipyrromethene as an NIR dye
  作者：Yuya Tomimori、Tetsuo Okujima、Tomoko Yano、Shigeki Mori、Noboru Ono、Hiroko Yamada、Hidemitsu Uno

  DOI：10.1016/j.tet.2011.03.016

  日期：2011.5

  A pi-expanded BODIPY dye with an intramolecular boronate skeleton was synthesized by retro Diets-Alder reaction of the bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY and the subsequent O-chelation. The photophysical and electrochemical properties were examined by UV-vis, fluorescence, CV measurements, and DFT calculation. This BODIPY exhibited the absorption and emission over a visible-NIR region at 600-850 nm. O-chelated BODIPY showed a bathocromic shift compared to F-BODIPYs. This dye showed a bright fluorescence emission at 733 nm with the high phi value of 0.58. (C) 2011 Elsevier Ltd. All rights reserved.