6-chloro-2,2-di(4-fluorophenyl)-2H-naphtho[1,2-b]pyran | 221680-18-8

• 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: 6-chloro-2,2-di(4-fluorophenyl)-2H-naphtho[1,2-b]pyran
• 英文别名: 6-Chloro-2,2-bis(4-fluorophenyl)benzo[h]chromene；6-chloro-2,2-bis(4-fluorophenyl)benzo[h]chromene
• CAS: 221680-18-8
• 化学式: C₂₅H₁₅ClF₂O
• 分子量: 404.843
• InChiKey: JRUABXZWIQLHHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2,2-di(4-fluorophenyl)-2H-naphtho[1,2-b]pyran 以 氘代乙腈 为溶剂， 反应 0.17h， 生成 2-[3,3-Bis-(4-fluoro-phenyl)-prop-2-en-(Z)-ylidene]-4-chloro-2H-naphthalen-1-one 、 2-[3,3-Bis-(4-fluoro-phenyl)-prop-2-en-(E)-ylidene]-4-chloro-2H-naphthalen-1-one
  参考文献：
  名称：

  Unexpected Halogen Substituent Effects on the Complex Thermal Relaxation of Naphthopyrans after UV Irradiation

  摘要：

  The kinetics of the thermal fading of four halogenated naphthopyrans (NP) have been analyzed using NMR spectroscopy in CD(3)CN. Two photomerocyanines (TT and TC) were detected after UV irradiation. The main relaxation process TC --> NP was coupled with TT/TC isomerization. The activation parameters of the various processes were rationalized by considering electronegativity and polarizability of the halogen substituents and their selective solvation by the electronegative nitrogen of acetonitrile.

  DOI：

  10.1021/jo050620o
• 作为产物：
  描述：

  2-[3,3-Bis-(4-fluoro-phenyl)-prop-2-en-(Z)-ylidene]-4-chloro-2H-naphthalen-1-one 以 氘代乙腈 为溶剂， 反应 0.17h， 生成 6-chloro-2,2-di(4-fluorophenyl)-2H-naphtho[1,2-b]pyran
  参考文献：
  名称：

  Unexpected Halogen Substituent Effects on the Complex Thermal Relaxation of Naphthopyrans after UV Irradiation

  摘要：

  The kinetics of the thermal fading of four halogenated naphthopyrans (NP) have been analyzed using NMR spectroscopy in CD(3)CN. Two photomerocyanines (TT and TC) were detected after UV irradiation. The main relaxation process TC --> NP was coupled with TT/TC isomerization. The activation parameters of the various processes were rationalized by considering electronegativity and polarizability of the halogen substituents and their selective solvation by the electronegative nitrogen of acetonitrile.

  DOI：

  10.1021/jo050620o

文献信息

• Complete assignment of the1H,13C and19F NMR spectra of fluoro-substituted 3H-naphthopyrans
  作者：Stéphanie Delbaere、Yannick Teral、Christophe Bochu、Mylène Campredon、Gaston Vermeersch

  DOI：10.1002/(sici)1097-458x(199902)37:2<159::aid-mrc427>3.0.co;2-4

  日期：1999.2

  The complete assignment of the H-1, C-13 and F-19 NMR spectra of eight fluoro-substituted 3H-naphthopyrans was achieved by the concerted application of homonuclear (H-1-H-1) and heteronuclear (C-13-H-1 and F-19-H-1) correlations. Copyright (C) 1999 John Wiley & Sons, Ltd.
• Unexpected Halogen Substituent Effects on the Complex Thermal Relaxation of Naphthopyrans after UV Irradiation
  作者：Stephanie Delbaere、Jean-Claude Micheau、Michel Frigoli、Gaston Vermeersch

  DOI：10.1021/jo050620o

  日期：2005.6.1

  The kinetics of the thermal fading of four halogenated naphthopyrans (NP) have been analyzed using NMR spectroscopy in CD(3)CN. Two photomerocyanines (TT and TC) were detected after UV irradiation. The main relaxation process TC --> NP was coupled with TT/TC isomerization. The activation parameters of the various processes were rationalized by considering electronegativity and polarizability of the halogen substituents and their selective solvation by the electronegative nitrogen of acetonitrile.