(7-methoxycoumarin-4-yl)methyl-4-methoxybenzoate | 76196-60-6

• 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-methoxybenzoate
• 英文别名: (7-Methoxy-2-oxochromen-4-yl)methyl 4-methoxybenzoate
• CAS: 76196-60-6
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: ZCWRHNAVBRCYER-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  536.8±50.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7-methoxycoumarin-4-yl)methyl-4-methoxybenzoate 在 HEPES buffer 作用下， 以 水 、 乙腈 为溶剂， 生成 4-(hydroxymethyl)-7-methoxycoumarin 、 大茴香酸
  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：

  7-methoxy-4-(p-toluenesulfonyl)hydrazonomethylcoumarin 在 sodium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.67h， 生成 (7-methoxycoumarin-4-yl)methyl-4-methoxybenzoate
  参考文献：
  名称：

  Takadate, Akira; Tahara, Tsutomu; Fujino, Hiroyuki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 11, p. 4120 - 4125

  摘要：

  DOI：

文献信息

• GUYA SHUJIRO; TAKADATE AKIRA; FUJINO HIROYUKI; TANAKA TOSHIAKI, YAKUGAKU ZASSHI, J. PHARM. SOC. JAP., 100, NO 7, 744-748
  作者：GUYA SHUJIRO、 TAKADATE AKIRA、 FUJINO HIROYUKI、 TANAKA TOSHIAKI

  DOI：——

  日期：——
• GOYA, SHUJIRO;TAKADATE, AKIRA;FUJINO, HIROYUKI, J. PHARM. SOC. JAP., 1982, 102, N 1, 63-68
  作者：GOYA, SHUJIRO、TAKADATE, AKIRA、FUJINO, HIROYUKI

  DOI：——

  日期：——
• TAKADATE, AKIRA;TAHARA, TSUTOMU;FUJINO, HIROYUKI;GOYA, SHUJIRO, CHEM. AND PHARM. BULL., 1982, 30, N 11, 4120-4125
  作者：TAKADATE, AKIRA、TAHARA, TSUTOMU、FUJINO, HIROYUKI、GOYA, SHUJIRO

  DOI：——

  日期：——
• 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).
• Takadate, Akira; Tahara, Tsutomu; Fujino, Hiroyuki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 11, p. 4120 - 4125
  作者：Takadate, Akira、Tahara, Tsutomu、Fujino, Hiroyuki、Goya, Shujiro

  DOI：——

  日期：——