11-(3-nitrophenyl)-6,7-dipentylbenzo[g]indolo[1,2-a][1,8]naphthyridine | 1612843-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 11-(3-nitrophenyl)-6,7-dipentylbenzo[g]indolo[1,2-a][1,8]naphthyridine
• 英文别名: 5-(3-Nitrophenyl)-11,12-dipentyl-2,21-diazapentacyclo[11.8.0.02,10.03,8.015,20]henicosa-1(21),3(8),4,6,9,11,13,15,17,19-decaene；5-(3-nitrophenyl)-11,12-dipentyl-2,21-diazapentacyclo[11.8.0.02,10.03,8.015,20]henicosa-1(21),3(8),4,6,9,11,13,15,17,19-decaene
• CAS: 1612843-15-8
• 化学式: C₃₅H₃₅N₃O₂
• 分子量: 529.682
• InChiKey: BZANNZHRNXEYNX-UHFFFAOYSA-N

物化性质

• 沸点：
  605.5±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8,11-dibromo-6,7-dipentylbenzo[g]indolo[1,2-a][1,8]naphthyridine 、 3-硝基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以28%的产率得到11-(3-nitrophenyl)-6,7-dipentylbenzo[g]indolo[1,2-a][1,8]naphthyridine
  参考文献：
  名称：

  Acid-Responsive Fluorescent Compounds Based on Nitro-Group-Substituted L-Shaped Pentacycles, Pyrrolo[1,2-a][1,8]naphthylidines

  摘要：

  Acid-responsive fluorescent compounds were prepared by introducing a nitrophenyl group to L-shaped pentacycles with a pyrrolo[1,2-a][1,8]naphthylidine backbone. These compounds show almost no fluorescence under neutral conditions, but emit green to orange fluorescence upon addition of trifluoroacetic acid. Acid titration experiments and NMR spectroscopy, plus DFT calculations, show that formation of a pyridinium cation species is responsible for the appearance of fluorescence.

  DOI：

  10.1021/ol501226x

文献信息

• Acid-Responsive Fluorescent Compounds Based on Nitro-Group-Substituted L-Shaped Pentacycles, Pyrrolo[1,2-<i>a</i>][1,8]naphthylidines
  作者：Kotaro Tateno、Rie Ogawa、Ryota Sakamoto、Mizuho Tsuchiya、Takashi Otani、Takao Saito

  DOI：10.1021/ol501226x

  日期：2014.6.20

  Acid-responsive fluorescent compounds were prepared by introducing a nitrophenyl group to L-shaped pentacycles with a pyrrolo[1,2-a][1,8]naphthylidine backbone. These compounds show almost no fluorescence under neutral conditions, but emit green to orange fluorescence upon addition of trifluoroacetic acid. Acid titration experiments and NMR spectroscopy, plus DFT calculations, show that formation of a pyridinium cation species is responsible for the appearance of fluorescence.