4-N-[(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl]-2'-deoxycytidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-[(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl]-2'-deoxycytidine
• 英文别名: (6-bromo-7-methoxy-2-oxochromen-4-yl)methyl N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• 化学式: C₂₁H₂₀BrN₃O₉
• 分子量: 538.308
• InChiKey: IATVWFDWBUPRPO-FDQGKXFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-N-[(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl]-2'-deoxycytidine 以 水 、 二甲基亚砜 为溶剂， 生成 6-bromo-4-(hydroxymethyl)-7-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Phototriggers for Nucleobases with Improved Photochemical Properties

  摘要：

  Synthesis and photochemical properties of new photoremovable protecting groups for nucleobases are described. Four caged 2'-deoxycytidines (dCs) were synthesized, and their photochemical properties were measured under simulated physiological conditions. Two new coumarin-caged dCs show better photochemical and photophysical properties than those of the caged dCs having previously reported caging groups.

  DOI：

  10.1021/ol702106t
• 作为产物：
  描述：

  (6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl chloride 、 2'-脱氧胞苷盐酸盐 在 吡啶 、 三甲基氯硅烷 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以45.1%的产率得到4-N-[(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl]-2'-deoxycytidine
  参考文献：
  名称：

  Phototriggers for Nucleobases with Improved Photochemical Properties

  摘要：

  Synthesis and photochemical properties of new photoremovable protecting groups for nucleobases are described. Four caged 2'-deoxycytidines (dCs) were synthesized, and their photochemical properties were measured under simulated physiological conditions. Two new coumarin-caged dCs show better photochemical and photophysical properties than those of the caged dCs having previously reported caging groups.

  DOI：

  10.1021/ol702106t