6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin | 566206-47-1

• 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-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin
• 英文别名: (6-bromo-7-hydroxycoumarin-4-yl)ethane-1,2-diol；6-Bromo-4-(1,2-dihydroxyethyl)-7-hydroxychromen-2-one
• CAS: 566206-47-1
• 化学式: C₁₁H₉BrO₅
• 分子量: 301.093
• InChiKey: KCWUPWOAZYEKCW-UHFFFAOYSA-N

物化性质

• 沸点：
  551.7±50.0 °C(Predicted)
• 密度：
  1.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  孕烯醇酮 、 6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin 在 4-甲基苯磺酸吡啶 、 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以10%的产率得到20-{3-(6-bromo-7-hydroxycoumarin-4-yl)methylethylendioxy}-5-pregnen-3-ol
  参考文献：
  名称：

  Caged Progesterone: A New Tool for Studying Rapid Nongenomic Actions of Progesterone

  摘要：

  Ketalization of the biomolecule progesterone with (6-bromo-7-hydroxycoumarin-4-yl)ethane-1,2-diol gives the photolabile progesterone derivatives 3 and 4. These compounds display dramatically reduced bioactivity and release progesterone upon irradiation with UV/vis or IR light. In particular, 4 can be used to perform concentration-jump experiments with high temporal and spatial resolution that allows one to study elegantly the mechanisms of rapid nongenomic cellular events evoked by progesterone. The usefulness of 4 was demonstrated by measurement of changes in swimming behavior of single human sperm caused by progesterone-induced Ca2+ influx in the sperm flagellum.

  DOI：

  10.1021/ja808334f
• 作为产物：
  描述：

  6-溴-4-(氯甲基)-7-羟基-2H-色烯-2-酮 在 吡啶 、 四氧化锇 、 水 、 sodium carbonate 、 氧化-4-甲基吗啉一水合物 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 24.5h， 生成 6-bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin
  参考文献：
  名称：

  Bhc-二醇作为醛和酮的光不稳定保护基。

  摘要：

  [反应：见正文] 6-溴-4-（1,2-二羟乙基）-7-羟基香豆素（Bhc-diol）可以在模拟的生理条件下用作醛和酮的可光去除保护基。证明了单光子和双光子诱导的苯甲醛，胡椒醛，苯乙酮和环己酮的释放。

  DOI：

  10.1021/ol034536b

文献信息

• [8-[Bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl Moieties as Photoremovable Protecting Groups for Compounds with COOH, NH₂, OH, and C═O Functions
  作者：Volker Hagen、Funda Kilic、Janina Schaal、Brigitte Dekowski、Reinhard Schmidt、Nico Kotzur

  DOI：10.1021/jo100368w

  日期：2010.5.7

  exemplarily for caging of a carboxylic acid, an amine, a phenol, and a carbonyl compound. The caged compounds are efficiently photolyzed at long-wavelength UV/vis irradiation. Compared to the corresponding (6-bromo-7-hydroxycoumarin-4-yl)methyl (Bhc) derivatives, the novel coumarin-type caged compounds are distinguished by (i) dramatically increased solubilities in aqueous buffers, (ii) lower pKa values

  我们引入了基于香豆素的可光活化保护基的变体，并将其示例性地用于羧酸，胺，苯酚和羰基化合物的笼蔽。笼状化合物可在长波紫外线/可见光照射下有效地光解。与相应的（6-bromo-7-hydroxycoumarin-4-yl）methyl（Bhc）衍生物相比，新型香豆素型笼状化合物的特征在于（i）在水性缓冲液中的溶解度显着提高，（ii）较低的p K a香豆素发色团的C 7羟基的最大分子量，因此允许在较低的pH下有效地释放光，并且（iii）在光保护的羰基化合物的情况下，具有更高的光解量子产率。光解的第一步以约10 9 s -1的速率常数发生。
• CONJUGATED POLYMERS WITH MULTISTAGE SIDE-CHAIN CLEAVAGE
  申请人：GEORGIA TECH RESEARCH CORPORATION

  公开号：US20210111346A1

  公开（公告）日：2021-04-15

  Multistage side-chain conjugated polymers (CPs) have a conjugated backbone from a multiplicity of repeating unit where at least one of the repeating units has a multistage side-chain. The repeating unit has a conjugated backbone portion and a multistage side-chain, which has one or more responsive functionalities. Responsive functionalities include a photo- or thermal-cleavable portion connected by a first linker between the backbone portion and the cleavable portion, and a chemically activatable solubilizing portion having an activatable functionality that can undergo a chemical reaction to provide aqueous solubility. The multistage side-chain CP is prepared in an organic solution and converted to an aqueous soluble activated multistage side-chain CP for deposited on a substrate. Upon cleavage, a multistage side-chain residue is liberated and removed from an insoluble core CP film that can be part of an organic electronic device.
• [EN] CONJUGATED POLYMERS WITH MULTISTAGE SIDE-CHAIN CLEAVAGE<br/>[FR] POLYMÈRES CONJUGUÉS AVEC CLIVAGE DE CHAÎNE LATÉRALE À PLUSIEURS ÉTAGES
  申请人：GEORGIA TECH RES INST

  公开号：WO2019005247A1

  公开（公告）日：2019-01-03

  Multistage side-chain conjugated polymers (CPs) have a conjugated backbone from a multiplicity of repeating unit where at least one of the repeating units has a multistage side- chain. The repeating unit has a conjugated backbone portion and a multistage side-chain, which has one or more responsive functionalities. Responsive functionalities include a photo- or thermal- cleavable portion connected by a first linker between the backbone portion and the cleavable portion, and a chemically activatable solubilizing portion having an activatable functionality that can undergo a chemical reaction to provide aqueous solubility. The multistage side-chain CP is prepared in an organic solution and converted to an aqueous soluble activated multistage side-chain CP for deposited on a substrate. Upon cleavage, a multistage side-chain residue is liberated and removed from an insoluble core CP film that can be part of an organic electronic device.
• Caged Progesterone: A New Tool for Studying Rapid Nongenomic Actions of Progesterone
  作者：Funda Kilic、Nachiket D. Kashikar、Reinhard Schmidt、Luis Alvarez、Luru Dai、Ingo Weyand、Burkhard Wiesner、Normann Goodwin、Volker Hagen、U. Benjamin Kaupp

  DOI：10.1021/ja808334f

  日期：2009.3.25

  Ketalization of the biomolecule progesterone with (6-bromo-7-hydroxycoumarin-4-yl)ethane-1,2-diol gives the photolabile progesterone derivatives 3 and 4. These compounds display dramatically reduced bioactivity and release progesterone upon irradiation with UV/vis or IR light. In particular, 4 can be used to perform concentration-jump experiments with high temporal and spatial resolution that allows one to study elegantly the mechanisms of rapid nongenomic cellular events evoked by progesterone. The usefulness of 4 was demonstrated by measurement of changes in swimming behavior of single human sperm caused by progesterone-induced Ca2+ influx in the sperm flagellum.
• Bhc-diol as a Photolabile Protecting Group for Aldehydes and Ketones
  作者：Min Lu、Olesya D. Fedoryak、Brent R. Moister、Timothy M. Dore

  DOI：10.1021/ol034536b

  日期：2003.6.1

  [reaction: see text] 6-Bromo-4-(1,2-dihydroxyethyl)-7-hydroxycoumarin (Bhc-diol) can be used under simulated physiological conditions as a photoremovable protecting group for aldehydes and ketones. The single- and two-photon-induced release of benzaldehyde, piperonal, acetophenone, and cyclohexanone is demonstrated.

  [反应：见正文] 6-溴-4-（1,2-二羟乙基）-7-羟基香豆素（Bhc-diol）可以在模拟的生理条件下用作醛和酮的可光去除保护基。证明了单光子和双光子诱导的苯甲醛，胡椒醛，苯乙酮和环己酮的释放。