3,3-diphenyl-3H-pyrano<3,2-a>carbazole | 152365-48-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3,3-diphenyl-3H-pyrano<3,2-a>carbazole
• 英文别名: 3,11-dihydro-3,3-diphenylpyrano[3,2-a]carbazole；3,3-diphenyl-3H,11H-pyrano[3,2-a]carbazole；Pyrano[3,2-a]carbazole, 3,11-dihydro-3,3-diphenyl-；3,3-diphenyl-11H-pyrano[3,2-a]carbazole
• CAS: 152365-48-5
• 化学式: C₂₇H₁₉NO
• 分子量: 373.454
• InChiKey: NQHLEDVYHAMMOS-UHFFFAOYSA-N

物化性质

• 沸点：
  598.2±50.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-diphenyl-3H-pyrano<3,2-a>carbazole 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.0h， 生成 1-[3,3-Diphenyl-prop-2-en-(Z)-ylidene]-9-methyl-1,9-dihydro-carbazol-2-one
  参考文献：
  名称：

  Synthesis and Photochromic Behaviour of Novel 2H-1-Benzopyrans (=2H-Chromenes) Derived from Carbazololes

  摘要：

  The synthesis and photochromic properties of new 2,2-diphenyl-2H-1-benzopyrans, fused to an indole moiety, are described. All compounds exhibit photochromic behaviour in solution at room temperature. The heteroanellation effects are variable and depend on the position and geometry of the fused indole moiety. A general bathochromic shift in the spectra of the open forms is observed. The presence of a N-methyl group prevents the broadening of the absorption spectra and promotes the instability of some photoinduced forms of compounds with the indole moiety fused at the 5,6 positions of the 2H-1-benzopyran skeleton. The enhanced photocolouration efficiency in the near-UV and the kinetics of thermal bleaching indicate that the novel compounds with an indole moiety fused at the 6,7 positions, particularly those with a linked thiophene moiety: are very interesting molecules for applications in the field of variable optical absorption systems.

  DOI：

  10.1002/1522-2675(20010516)84:5<1163::aid-hlca1163>3.0.co;2-t
• 作为产物：
  描述：

  2-羟基咔唑 、 β-苯基肉桂醛 在 titanium(IV) tetraethanolate 作用下， 生成 3,3-diphenyl-3H-pyrano<3,2-a>carbazole
  参考文献：
  名称：

  A convenient synthesis of azolo-fused 2H-[1] benzopyrans

  摘要：

  The synthesis of substituted 7;7-diphenyl-7H-pyrano[3,2-e]benzazoles 2a-f and 7,7-diphenyl-7H-pyrano[2,3-g]benzazoles 4a-d is described. Thus, suitable titanium(IV) phenolates reacted with beta-phenylcinnamaldehyde in refluxing aprotic non-polar solvents. Electrocyclisation of o-quinone allides generated in situ gives regiospecifically the title compounds. Stoichiometric amounts of heterocyclic phenol, titanium tetraethoxide and the carbonyl compound, have been found to give better results. In this series. substitution on the a position leads to the formation of the regioisomer. The method could be also extended to the formation of 8,8-diphenyl-8H-pyrano[2.3-e]benzazole 8. A side reaction between the desired pyran and a second molecule of heterocyclic phenol was observed. This condensation product 9 was isolated and characterized in the case of the imidazole derivative, and a mechanism for its formation is proposed.

  DOI：

  10.1039/p19940002591

文献信息

• A convenient synthesis of azolo-fused 2H-[1] benzopyrans
  作者：Jean-Luc Pozzo、Vladimir A. Lokshin、Robert Guglielmetti

  DOI：10.1039/p19940002591

  日期：——

  The synthesis of substituted 7;7-diphenyl-7H-pyrano[3,2-e]benzazoles 2a-f and 7,7-diphenyl-7H-pyrano[2,3-g]benzazoles 4a-d is described. Thus, suitable titanium(IV) phenolates reacted with beta-phenylcinnamaldehyde in refluxing aprotic non-polar solvents. Electrocyclisation of o-quinone allides generated in situ gives regiospecifically the title compounds. Stoichiometric amounts of heterocyclic phenol, titanium tetraethoxide and the carbonyl compound, have been found to give better results. In this series. substitution on the a position leads to the formation of the regioisomer. The method could be also extended to the formation of 8,8-diphenyl-8H-pyrano[2.3-e]benzazole 8. A side reaction between the desired pyran and a second molecule of heterocyclic phenol was observed. This condensation product 9 was isolated and characterized in the case of the imidazole derivative, and a mechanism for its formation is proposed.
• Synthesis and Photochromic Behaviour of Novel 2H-1-Benzopyrans (=2H-Chromenes) Derived from Carbazololes
  作者：M. Manuel Oliveira、Luis M. Carvalho、Corinne Moustrou、André Samat、Robert Guglielmetti、Ana M. F. Oliveira-Campos

  DOI：10.1002/1522-2675(20010516)84:5<1163::aid-hlca1163>3.0.co;2-t

  日期：2001.5.16

  The synthesis and photochromic properties of new 2,2-diphenyl-2H-1-benzopyrans, fused to an indole moiety, are described. All compounds exhibit photochromic behaviour in solution at room temperature. The heteroanellation effects are variable and depend on the position and geometry of the fused indole moiety. A general bathochromic shift in the spectra of the open forms is observed. The presence of a N-methyl group prevents the broadening of the absorption spectra and promotes the instability of some photoinduced forms of compounds with the indole moiety fused at the 5,6 positions of the 2H-1-benzopyran skeleton. The enhanced photocolouration efficiency in the near-UV and the kinetics of thermal bleaching indicate that the novel compounds with an indole moiety fused at the 6,7 positions, particularly those with a linked thiophene moiety: are very interesting molecules for applications in the field of variable optical absorption systems.

表征谱图