(6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) carbonate | 640720-93-0

• 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: (6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) carbonate
• CAS: 640720-93-0
• 化学式: C₂₃H₂₅BrO₁₁
• 分子量: 557.349
• InChiKey: SLXOLLFBRZSQRF-DABHTEOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  132.12
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) carbonate 在 KMOPS buffer 、 水 作用下， 以 二甲基亚砜 为溶剂， 生成 二氧化碳 、 双丙酮半乳糖 、 6-溴-7-羟基-4-(羟甲基)香豆素
  参考文献：
  名称：

  Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols

  摘要：

  [GRAPHICS]Caged compounds can be used to regulate the spatial and temporal dynamics of signaling molecules in live cells. Photochemical properties of coumarin-4-ylmethoxy carbonates (1a-d) are investigated to construct caged compounds of hydroxy-containing molecules. All the compounds possess desired properties as phototriggers for alcohols and phenols. The 6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl (Bhcmoc) group has the highest photochemical efficiency and is applied to make caged compounds of 1,2-dioctanoylglycerol (diC(8)), Tyr-OMe, and adenosine.

  DOI：

  10.1021/ol0359362
• 作为产物：
  描述：

  6-bromo-7-(methoxymethoxy)-4-(hydroxymethyl)coumarin 在 4-二甲氨基吡啶 、 KMOPS buffer 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 34.67h， 生成 (6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) carbonate
  参考文献：
  名称：

  Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols

  摘要：

  [GRAPHICS]Caged compounds can be used to regulate the spatial and temporal dynamics of signaling molecules in live cells. Photochemical properties of coumarin-4-ylmethoxy carbonates (1a-d) are investigated to construct caged compounds of hydroxy-containing molecules. All the compounds possess desired properties as phototriggers for alcohols and phenols. The 6-bromo-7-hydroxycoumarin-4-ylmethoxycarbonyl (Bhcmoc) group has the highest photochemical efficiency and is applied to make caged compounds of 1,2-dioctanoylglycerol (diC(8)), Tyr-OMe, and adenosine.

  DOI：

  10.1021/ol0359362