(7-methoxycoumarin-4-yl)methyl-4-cyanobenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (7-methoxycoumarin-4-yl)methyl-4-cyanobenzoate
• 英文别名: (7-Methoxy-2-oxochromen-4-yl)methyl 4-cyanobenzoate
• 化学式: C₁₉H₁₃NO₅
• 分子量: 335.316
• InChiKey: POZSPBXEQWLTMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-溴甲基-7-甲氧基香豆素	4-(bromomethyl)-7-methoxycoumarin	35231-44-8	C11H9BrO3	269.095

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-(hydroxymethyl)-7-methoxycoumarin	72433-26-2	C11H10O4	206.198

反应信息

• 作为反应物：
  描述：

  (7-methoxycoumarin-4-yl)methyl-4-cyanobenzoate 在 HEPES buffer 作用下， 以 水 、 乙腈 为溶剂， 生成 对氰基苯甲酸 、 4-(hydroxymethyl)-7-methoxycoumarin
  参考文献：
  名称：

  Deactivation Behavior and Excited-State Properties of (Coumarin-4-yl)methyl Derivatives. 1. Photocleavage of (7-Methoxycoumarin-4-yl)methyl-Caged Acids with Fluorescence Enhancement

  摘要：

  The photochemistry of the (7-methoxycoumarin-4-yl)methyl (MCM) carboxylates 3a-d, the mesylate 4, and the phosphates 5a-e has been examined under near physiological conditions in acetonitrile or methanol/aqueous HEPES buffer solution, respectively Analysis of photoproducts as well as measurements of photochemical quantum yields, fluorescence quantum yields, and lifetimes for the excited singlet state verified the similar photochemical and photophysical behavior of all the esters studied here. 4-(Hydroxymethyl)-7-methoxycoumarin (2) and the corresponding free acids were obtained as major products upon irradiation. The rates of deactivation of the excited MCM derivatives 3a-5e were found to be dependent on the:leaving group ability of the anion concerned as well as on the solvent polarity. The polarity dependence and the exclusive formation of O-18-labeled 2 during irradiation of 5a in O-18-labeled water indicate that photocleavage of the excited singlet state of the MCM caged compounds 3a-5e proceeds via a photo S(N)1 mechanism (solvent-assisted photoheterolysis).

  DOI：

  10.1021/jo9910233
• 作为产物：
  描述：

  对氰基苯甲酸 、 4-溴甲基-7-甲氧基香豆素 在 potassium fluoride 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以83.8%的产率得到(7-methoxycoumarin-4-yl)methyl-4-cyanobenzoate
  参考文献：
  名称：

  Deactivation Behavior and Excited-State Properties of (Coumarin-4-yl)methyl Derivatives. 1. Photocleavage of (7-Methoxycoumarin-4-yl)methyl-Caged Acids with Fluorescence Enhancement

  摘要：

  The photochemistry of the (7-methoxycoumarin-4-yl)methyl (MCM) carboxylates 3a-d, the mesylate 4, and the phosphates 5a-e has been examined under near physiological conditions in acetonitrile or methanol/aqueous HEPES buffer solution, respectively Analysis of photoproducts as well as measurements of photochemical quantum yields, fluorescence quantum yields, and lifetimes for the excited singlet state verified the similar photochemical and photophysical behavior of all the esters studied here. 4-(Hydroxymethyl)-7-methoxycoumarin (2) and the corresponding free acids were obtained as major products upon irradiation. The rates of deactivation of the excited MCM derivatives 3a-5e were found to be dependent on the:leaving group ability of the anion concerned as well as on the solvent polarity. The polarity dependence and the exclusive formation of O-18-labeled 2 during irradiation of 5a in O-18-labeled water indicate that photocleavage of the excited singlet state of the MCM caged compounds 3a-5e proceeds via a photo S(N)1 mechanism (solvent-assisted photoheterolysis).

  DOI：

  10.1021/jo9910233

文献信息

• Deactivation Behavior and Excited-State Properties of (Coumarin-4-yl)methyl Derivatives. 1. Photocleavage of (7-Methoxycoumarin-4-yl)methyl-Caged Acids with Fluorescence Enhancement
  作者：Björn Schade、Volker Hagen、Reinhard Schmidt、Ralph Herbrich、Eberhard Krause、Torsten Eckardt、Jürgen Bendig

  DOI：10.1021/jo9910233

  日期：1999.12.1

  The photochemistry of the (7-methoxycoumarin-4-yl)methyl (MCM) carboxylates 3a-d, the mesylate 4, and the phosphates 5a-e has been examined under near physiological conditions in acetonitrile or methanol/aqueous HEPES buffer solution, respectively Analysis of photoproducts as well as measurements of photochemical quantum yields, fluorescence quantum yields, and lifetimes for the excited singlet state verified the similar photochemical and photophysical behavior of all the esters studied here. 4-(Hydroxymethyl)-7-methoxycoumarin (2) and the corresponding free acids were obtained as major products upon irradiation. The rates of deactivation of the excited MCM derivatives 3a-5e were found to be dependent on the:leaving group ability of the anion concerned as well as on the solvent polarity. The polarity dependence and the exclusive formation of O-18-labeled 2 during irradiation of 5a in O-18-labeled water indicate that photocleavage of the excited singlet state of the MCM caged compounds 3a-5e proceeds via a photo S(N)1 mechanism (solvent-assisted photoheterolysis).