6,7-dimethoxy-4-(hydroxymethyl)coumarin | 402755-39-9

• 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: 6,7-dimethoxy-4-(hydroxymethyl)coumarin
• 英文别名: 4-(Hydroxymethyl)-6,7-dimethoxy-2H-1-benzopyran-2-one；4-(hydroxymethyl)-6,7-dimethoxychromen-2-one
• CAS: 402755-39-9
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: MUFUSMCPWMZMON-UHFFFAOYSA-N

物化性质

• 沸点：
  449.9±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯磷酸二乙酯 、 6,7-dimethoxy-4-(hydroxymethyl)coumarin 在 吡啶 作用下， 以68%的产率得到(6,7-dimethoxycoumarin-4-yl)methyl diethyl phosphate
  参考文献：
  名称：

  （Coumarin-4-yl）甲酯是质子的高效超快光触发剂，可用于酸化膜表面。

  摘要：

  DOI：

  10.1002/anie.200461567
• 作为产物：
  描述：

  4-溴甲基-6,7-二甲氧基香豆素 在 盐酸 作用下， 以 乙醇 、 水 、 乙酸酐 为溶剂， 生成 6,7-dimethoxy-4-(hydroxymethyl)coumarin
  参考文献：
  名称：

  （香豆素-4-基）甲基衍生物的失活行为和激发态性质。2.具有荧光增强作用的所选（香豆素-4-基）甲基笼罩的腺苷环3'，5'-单磷酸的光裂解。

  摘要：

  （香豆素-4-基）甲基笼罩的腺苷环3'，5'-单磷酸酯（cAMPs）1-6的一系列轴向和赤道非对映异构体，在6-和/或-中具有甲氧基，二烷基氨基或无取代基已经合成了7位和它们相应的4-（羟甲基）香豆素光产物7-12。在甲醇/ HEPES缓冲溶液中检测了1-6和7-12的光化学和UV / vis光谱特性（吸收和荧光）。供体在6-位的取代引起长波长吸收带的强烈的红移，而在7-位的取代仅导致弱的红移。笼养的cAMPs的光化学裂解进行了调查，并分析了光产物。光化学量子产率，荧光量子产率，确定了激发单重态的寿命。使用中间形成的香豆基甲基阳离子的电子稳定作用，在香豆素部分的7位具有供体取代基的笼状cAMP中，获得了最高的光化学量子产率值（光S（N）1机理）。用6-位供体取代时，香豆素甲基阳离子的适度电子稳定作用被强的红移引起过度补偿，从而减小了激发态S（1）与相应香豆素甲基阳离子之间的能隙。cAMP的

  DOI：

  10.1021/jo010692p

文献信息

• 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.
• PHOTOCLEAVABLE PROTECTING GROUPS
  申请人：Barone Anthony D.

  公开号：US20090076295A1

  公开（公告）日：2009-03-19

  Novel compounds are provided, which are useful as linking groups in chemical synthesis, preferably in the solid phase synthesis of oligonucleotides and polypeptides. These compounds are generally photolabile and comprise protecting groups which can be removed by photolysis to unmask a reactive group. The protecting group has the general formula Y, wherein Y is a chemical structure as shown in FIG. 1 . Also provided is a method of forming, from component molecules, a plurality of compounds on a support, each compound occupying a separate predefined region of the support, using the protected compounds described above.
• Photocleavable Protecting Groups
  申请人：Barone Anthony D.

  公开号：US20100324266A1

  公开（公告）日：2010-12-23

  Novel compounds are provided, which are useful as linking groups in chemical synthesis, preferably in the solid phase synthesis of oligonucleotides and polypeptides. These compounds are generally photolabile and comprise protecting groups which can be removed by photolysis to unmask a reactive group. The protecting group has the general formula Y, wherein Y is a chemical structure as shown in FIG. 1 . Also provided is a method of forming, from component molecules, a plurality of compounds on a support, each compound occupying a separate predefined region of the support, using the protected compounds described above.
• Deactivation Behavior and Excited-State Properties of (Coumarin-4-yl)methyl Derivatives. 2. Photocleavage of Selected (Coumarin-4-yl)methyl-Caged Adenosine Cyclic 3‘,5‘-Monophosphates with Fluorescence Enhancement
  作者：Torsten Eckardt、Volker Hagen、Björn Schade、Reinhardt Schmidt、Claude Schweitzer、Jürgen Bendig

  DOI：10.1021/jo010692p

  日期：2002.2.1

  UV/vis spectroscopical properties (absorption and fluorescence) of 1-6 and 7-12 have been examined in methanol/aqueous HEPES buffer solution. Donor substitution in the 6-position causes a strong bathochromic shift of the long-wavelength absorption band, whereas substitution in the 7-position leads only to a weak red shift. The photochemical cleavage of the caged cAMPs was investigated, and the photoproducts

  （香豆素-4-基）甲基笼罩的腺苷环3'，5'-单磷酸酯（cAMPs）1-6的一系列轴向和赤道非对映异构体，在6-和/或-中具有甲氧基，二烷基氨基或无取代基已经合成了7位和它们相应的4-（羟甲基）香豆素光产物7-12。在甲醇/ HEPES缓冲溶液中检测了1-6和7-12的光化学和UV / vis光谱特性（吸收和荧光）。供体在6-位的取代引起长波长吸收带的强烈的红移，而在7-位的取代仅导致弱的红移。笼养的cAMPs的光化学裂解进行了调查，并分析了光产物。光化学量子产率，荧光量子产率，确定了激发单重态的寿命。使用中间形成的香豆基甲基阳离子的电子稳定作用，在香豆素部分的7位具有供体取代基的笼状cAMP中，获得了最高的光化学量子产率值（光S（N）1机理）。用6-位供体取代时，香豆素甲基阳离子的适度电子稳定作用被强的红移引起过度补偿，从而减小了激发态S（1）与相应香豆素甲基阳离子之间的能隙。cAMP的
• (Coumarin-4-yl)methyl Esters as Highly Efficient, Ultrafast Phototriggers for Protons and Their Application to Acidifying Membrane Surfaces
  作者：Daniel Geißler、Yuri N. Antonenko、Reinhard Schmidt、Sandro Keller、Oxana O. Krylova、Burkhard Wiesner、Jürgen Bendig、Peter Pohl、Volker Hagen

  DOI：10.1002/anie.200461567

  日期：2005.2.11