(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl chloride | 959845-41-1

• 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-methoxycoumarin-4-yl)methoxycarbonyl chloride
• 英文别名: (6-Bromo-7-methoxy-2-oxochromen-4-yl)methyl carbonochloridate；(6-bromo-7-methoxy-2-oxochromen-4-yl)methyl carbonochloridate
• CAS: 959845-41-1
• 化学式: C₁₂H₈BrClO₅
• 分子量: 347.55
• InChiKey: FCLZJSXIYUHALM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl chloride 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 tert-butyl N-[2-(N-9-fluorenylmethoxycarbonyl)aminoethyl]-N-[{4-N-(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl-cytosin-1-yl}acetyl]glycinate
  参考文献：
  名称：

  Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties

  摘要：

  一个具有（6-溴-7-甲氧基香豆素）-4-甲氧羰基（Bmcmoc）保护基团的核碱基保护的肽核酸（PNA）被新合成。

  DOI：

  10.1039/c4ob00418c
• 作为产物：
  描述：

  光气 、 6-bromo-4-(hydroxymethyl)-7-methoxy-2H-chromen-2-one 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.5h， 以71%的产率得到(6-bromo-7-methoxycoumarin-4-yl)methoxycarbonyl chloride
  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

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.
• Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties
  作者：Takayoshi Watanabe、Tomoko Hoshida、Jun Sakyo、Mariko Kishi、Satoshi Tanabe、Junichi Matsuura、Shingo Akiyama、Makiko Nakata、Yasuaki Tanabe、Akinobu Z. Suzuki、Soichiro Watanabe、Toshiaki Furuta

  DOI：10.1039/c4ob00418c

  日期：——

  A nucleobase-caged peptide nucleic acid (PNA) having a (6-bromo-7-methoxycoumarin)-4-ylmethoxycarbonyl (Bmcmoc) caging group was newly synthesized.

  一个具有（6-溴-7-甲氧基香豆素）-4-甲氧羰基（Bmcmoc）保护基团的核碱基保护的肽核酸（PNA）被新合成。