3-methoxy-5,6-dihydrobenzoxanthylium perchlorate | 38107-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-methoxy-5,6-dihydrobenzoxanthylium perchlorate
• 英文别名: 3-Methoxy-5,6-dihydrobenzo[c]xanthen-12-ium;perchlorate
• CAS: 38107-45-8
• 化学式: C₁₈H₁₅O₂*ClO₄
• 分子量: 362.766
• InChiKey: HYKLHAMASOXSGB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-5,6-dihydrobenzoxanthylium perchlorate 在 盐酸 、 sodium hydroxide 、 磷酸 、 硼酸 、 溶剂黄146 作用下， 生成 2-[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Hydrolysis of Benzopyrylium Dyes - An Application of the Concept of Chemical Hardness

  摘要：

  A systematic study on the relationship between the substitution pattern, the pK(a) values, and spectral properties of flavylium cations and the respective-(CH2)(2)-bridged analoga (5,6-dihydrobenzo[c]xanthylium cations) is given in order to find rules concerning their spectral behaviour and their chemical reactivity.Our results show that the concept of chemical hardness can explain the different reactivity of 4'- and 7'-substituted flavylium ions against HO-. The pK(a) values of these species, which can act as a measure of reactivity with respect to a nucleophile, correlate linearly with the absolute hardness calculated from half the energy gap between the frontier orbitals. Since the longest-wavelength UV/VIS absorption maximum is mainly determined by the HOMO-LUMO transition, an analogous linear correlation is obtained between the spectral 0-0 transition and the pK(a) value. Deviations from these correlations are assumed to be due to steric effects.

  DOI：

  10.1002/prac.199633801142
• 作为产物：
  描述：

  2-[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-6-methoxy-3,4-dihydro-2H-naphthalen-1-one 在 盐酸 、 sodium hydroxide 、 磷酸 、 硼酸 、 溶剂黄146 作用下， 生成 3-methoxy-5,6-dihydrobenzoxanthylium perchlorate
  参考文献：
  名称：

  Hydrolysis of Benzopyrylium Dyes - An Application of the Concept of Chemical Hardness

  摘要：

  A systematic study on the relationship between the substitution pattern, the pK(a) values, and spectral properties of flavylium cations and the respective-(CH2)(2)-bridged analoga (5,6-dihydrobenzo[c]xanthylium cations) is given in order to find rules concerning their spectral behaviour and their chemical reactivity.Our results show that the concept of chemical hardness can explain the different reactivity of 4'- and 7'-substituted flavylium ions against HO-. The pK(a) values of these species, which can act as a measure of reactivity with respect to a nucleophile, correlate linearly with the absolute hardness calculated from half the energy gap between the frontier orbitals. Since the longest-wavelength UV/VIS absorption maximum is mainly determined by the HOMO-LUMO transition, an analogous linear correlation is obtained between the spectral 0-0 transition and the pK(a) value. Deviations from these correlations are assumed to be due to steric effects.

  DOI：

  10.1002/prac.199633801142

文献信息

• Hydrolysis of Benzopyrylium Dyes - An Application of the Concept of Chemical Hardness
  作者：Heike Lietz、G�nter Haucke、Peter Czerney、Birgit John

  DOI：10.1002/prac.199633801142

  日期：——

  A systematic study on the relationship between the substitution pattern, the pK(a) values, and spectral properties of flavylium cations and the respective-(CH2)(2)-bridged analoga (5,6-dihydrobenzo[c]xanthylium cations) is given in order to find rules concerning their spectral behaviour and their chemical reactivity.Our results show that the concept of chemical hardness can explain the different reactivity of 4'- and 7'-substituted flavylium ions against HO-. The pK(a) values of these species, which can act as a measure of reactivity with respect to a nucleophile, correlate linearly with the absolute hardness calculated from half the energy gap between the frontier orbitals. Since the longest-wavelength UV/VIS absorption maximum is mainly determined by the HOMO-LUMO transition, an analogous linear correlation is obtained between the spectral 0-0 transition and the pK(a) value. Deviations from these correlations are assumed to be due to steric effects.