(7-methoxycoumarin-4-yl)methyl guanosine cyclic-3',5'-monophosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: (7-methoxycoumarin-4-yl)methyl guanosine cyclic-3',5'-monophosphate
• 英文别名: 9-[(2R,4aR,6R,7R,7aS)-7-hydroxy-2-[(7-methoxy-2-oxochromen-4-yl)methoxy]-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one
• 化学式: C₂₁H₂₀N₅O₁₀P
• 分子量: 533.391
• InChiKey: IIQBVLBDYUGWRN-HCJMKVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  195
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (7-methoxycoumarin-4-yl)methyl guanosine cyclic-3',5'-monophosphate 在 HEPES buffer 作用下， 以 甲醇 、 水 为溶剂， 生成 4-(hydroxymethyl)-7-methoxycoumarin 、 cyclic guanosine 3',5'-monophosphate
  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：

  4-diazomethyl-7-methoxycoumarin 、 cyclic guanosine 3',5'-monophosphate 以 二甲基亚砜 、 乙腈 为溶剂， 反应 24.0h， 生成 (7-methoxycoumarin-4-yl)methyl guanosine cyclic-3',5'-monophosphate 、 (7-methoxycoumarin-4-yl)methyl guanosine cyclic-3',5'-monophosphate
  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).