2-(bromomethyl)-8-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole | 1254122-48-9

• 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: 2-(bromomethyl)-8-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole
• 英文别名: 2-(Bromomethyl)-8-methylpyrano[3,2-f][1,3]benzoxazol-6-one；2-(bromomethyl)-8-methylpyrano[3,2-f][1,3]benzoxazol-6-one
• CAS: 1254122-48-9
• 化学式: C₁₂H₈BrNO₃
• 分子量: 294.104
• InChiKey: VSHSRKGPRRVMGY-UHFFFAOYSA-N

物化性质

• 熔点：
  220.1-221.4 °C
• 沸点：
  430.4±40.0 °C(predicted)
• 密度：
  1.683±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-CBZ-beta-丙氨酸 、 2-(bromomethyl)-8-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以95%的产率得到(8-Methyl-6-oxopyrano[3,2-f][1,3]benzoxazol-2-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  Oxazole light triggered protecting groups: synthesis and photolysis of fused heteroaromatic conjugates

  摘要：

  Fused oxazole derivatives were synthesized and evaluated as new light triggered protecting groups by using amino acids as model bifunctional molecules. The photosensitivity of ester conjugates was tested under irradiation at 254, 300, and 350 nm. Oxazole conjugates were readily photolyzed with complete release of the amino acid, the best results obtained for naphtho[2,3-d]oxazole at 254 and 300 nm, being the first reported application of this type of heterocycles as photocleavable protecting groups for carboxylic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.020
• 作为产物：
  描述：

  6-氨基-7-羟基-4-甲基香豆素 、 溴乙酸 在 polyphosphoric acid 作用下， 反应 4.0h， 以23%的产率得到2-(bromomethyl)-8-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole
  参考文献：
  名称：

  Oxazole light triggered protecting groups: synthesis and photolysis of fused heteroaromatic conjugates

  摘要：

  Fused oxazole derivatives were synthesized and evaluated as new light triggered protecting groups by using amino acids as model bifunctional molecules. The photosensitivity of ester conjugates was tested under irradiation at 254, 300, and 350 nm. Oxazole conjugates were readily photolyzed with complete release of the amino acid, the best results obtained for naphtho[2,3-d]oxazole at 254 and 300 nm, being the first reported application of this type of heterocycles as photocleavable protecting groups for carboxylic acids. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.020

文献信息

• Photolytic Release of Butyric Acid from Oxygen- and Nitrogen-Based Heteroaromatic Cages
  作者：Ana M. S. Soares、Ana M. Piloto、Graham Hungerford、Susana P. G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1002/ejoc.201101392

  日期：2012.2

  In order to develop butyric acid photoactive prodrugs, new heteroaromatic conjugates based on oxygen and nitrogen were synthesised and evaluated under irradiation at 254, 300, 350 and 419 nm. Light-triggered uncaging of butyric acid from the corresponding heterocyclic cages was achieved with complete release of the drug in short times. Naphtho[2,3-d]oxazole, naphtho[1,2-d]oxazole, 3-oxo-3H-benzo[f]benzopyran

  为了开发丁酸光活性前药，合成了基于氧和氮的新型杂芳族共轭物，并在 254、300、350 和 419 nm 的辐射下进行了评估。在短时间内完全释放药物，实现了丁酸从相应的杂环笼中的光触发解笼。萘并[2,3-d]恶唑、萘并[1,2-d]恶唑、3-氧代-3H-苯并[f]苯并吡喃、2-氧代-2H-苯并[h]苯并吡喃和6-氧代-6H-苯并吡喃[6,7-d]恶唑偶联物很容易被光解，并且在254和300 nm处获得了萘并恶唑和3-氧代-3H-苯并[f]苯并吡喃，2-氧代-2H-苯并获得最佳结果[h] 苯并吡喃和 2-methyl-6-oxo-6H-benzopyrano[6,7-d] 恶唑在 350 nm。3-Oxo-3H-benzo[f]benzopyran 在 419 nm 处也提供了良好的结果。