[[6-bromo-7-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl chloride | 640721-03-5

• 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-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl chloride
• 英文别名: MOMBhcmoc-Cl；[6-Bromo-7-(methoxymethoxy)-2-oxochromen-4-yl]methyl carbonochloridate；[6-bromo-7-(methoxymethoxy)-2-oxochromen-4-yl]methyl carbonochloridate
• CAS: 640721-03-5
• 化学式: C₁₃H₁₀BrClO₆
• 分子量: 377.576
• InChiKey: OINGSHCDLOESJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  [[6-bromo-7-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl chloride 在 4-二甲氨基吡啶 、 KMOPS buffer 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 4.67h， 生成 phenyl (6-bromo-7-hydroxycoumarin-4-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
• 作为产物：
  描述：

  6-溴-4-(氯甲基)-7-羟基-2H-色烯-2-酮 在 水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 53.0h， 生成 [[6-bromo-7-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl chloride
  参考文献：
  名称：

  A new tool to assess ceramide bioactivity: 6-bromo-7-hydroxycoumarinyl-caged ceramide

  摘要：

  迄今为止，天然长链神经酰胺的生物活性研究都是在将其溶于含有十二烷的有机溶剂混合物后提供给细胞进行的。我们合成了与(6-溴-7-羟基香豆素-4-基)甲基团偶联的神经酰胺。光笼式神经酰胺在中性pH的水溶液中用350 nm光可以有效释放，从而提供了一种有前景的新工具来研究神经酰胺的特性。

  DOI：

  10.1039/c1cc12345a

文献信息

• A clickable caging group as a new platform for modular caged compounds with improved photochemical properties
  作者：Akinobu Z. Suzuki、Ryota Sekine、Shiori Takeda、Ryosuke Aikawa、Yukiko Shiraishi、Tomomi Hamaguchi、Hiroyuki Okuno、Hirokazu Tamamura、Toshiaki Furuta

  DOI：10.1039/c8cc07981a

  日期：——

  A 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc) caged compound having a click-modifiable chemical handle was designed and synthesized. This molecule was applied to the synthesis of modular caged paclitaxels (PTXs) in which additional functional units could be easily installed. This system was used to prepare water-soluble caged PTXs with improved photolysis efficiencies.

  设计并合成了具有可点击修饰的化学手感的6-溴-7-羟基香豆素-4-基甲基（Bhc）笼状化合物。该分子被应用于模块笼式紫杉醇（PTX）的合成，其中可以轻松安装其他功能单元。该系统用于制备具有改善的光解效率的水溶性笼状PTX。
• Phototriggers for Nucleobases with Improved Photochemical Properties
  作者：Toshiaki Furuta、Takayoshi Watanabe、Satoshi Tanabe、Jun Sakyo、Chie Matsuba

  DOI：10.1021/ol702106t

  日期：2007.11.1

  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.
• US2014/256015
  申请人：——

  公开号：——

  公开（公告）日：——
• Coumarin-4-ylmethoxycarbonyls as Phototriggers for Alcohols and Phenols
  作者：Akinobu Z. Suzuki、Takayoshi Watanabe、Mika Kawamoto、Keiko Nishiyama、Hirotaka Yamashita、Megumi Ishii、Michiko Iwamura、Toshiaki Furuta

  DOI：10.1021/ol0359362

  日期：2003.12.1

  [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.
• A new tool to assess ceramide bioactivity: 6-bromo-7-hydroxycoumarinyl-caged ceramide
  作者：Young Ah Kim、Daniel M. Carter Ramirez、Willard J. Costain、Linda J. Johnston、Robert Bittman

  DOI：10.1039/c1cc12345a

  日期：——

  The bioactivity of natural, long-chain ceramides has until now been studied after its delivery to cells in organic solvent mixtures containing dodecane. We have synthesized ceramides conjugated to a (6-bromo-7-hydroxycoumarin-4-yl)methyl group. The photocaged ceramide is efficiently released with 350 nm light in aqueous solution at neutral pH, thus providing a promising new tool to study ceramide's properties.

  迄今为止，天然长链神经酰胺的生物活性研究都是在将其溶于含有十二烷的有机溶剂混合物后提供给细胞进行的。我们合成了与(6-溴-7-羟基香豆素-4-基)甲基团偶联的神经酰胺。光笼式神经酰胺在中性pH的水溶液中用350 nm光可以有效释放，从而提供了一种有前景的新工具来研究神经酰胺的特性。