(8-Methyl-6-oxopyrano[3,2-f][1,3]benzoxazol-2-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate | 1254122-55-8

• 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: (8-Methyl-6-oxopyrano[3,2-f][1,3]benzoxazol-2-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate
• 英文别名: (8-methyl-6-oxopyrano[3,2-f][1,3]benzoxazol-2-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate
• CAS: 1254122-55-8
• 化学式: C₂₃H₂₀N₂O₇
• 分子量: 436.421
• InChiKey: CNBKJMYAPLMQMY-UHFFFAOYSA-N

物化性质

• 熔点：
  114.6-115.4 °C
• 沸点：
  655.8±55.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (8-Methyl-6-oxopyrano[3,2-f][1,3]benzoxazol-2-yl)methyl 3-(phenylmethoxycarbonylamino)propanoate 在 甲醇 作用下， 反应 0.46h， 生成 N-CBZ-beta-丙氨酸
  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：

  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

文献信息

• Oxazole light triggered protecting groups: synthesis and photolysis of fused heteroaromatic conjugates
  作者：Ana M.S. Soares、Susana P.G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2010.08.020

  日期：2010.10

  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.