N-benzyloxycarbonyl-L-phenylalanine (7-methylcoumarin-4-yl)methyl ester | 1246656-08-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyloxycarbonyl-L-phenylalanine (7-methylcoumarin-4-yl)methyl ester
• 英文别名: (7-methyl-2-oxochromen-4-yl)methyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1246656-08-5
• 化学式: C₂₈H₂₅NO₆
• 分子量: 471.51
• InChiKey: SDYAUNJNGGCGEZ-DEOSSOPVSA-N

物化性质

• 熔点：
  151-152 °C(Solvent: Ethyl acetate; Ligroine)
• 沸点：
  675.5±55.0 °C(predicted)
• 密度：
  1.265±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94.84
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-phenylalanine (7-methylcoumarin-4-yl)methyl ester 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以70%的产率得到N-benzyloxycarbonyl-L-phenylalanine (7-methyl-2-thioxobenzopyran-4-yl)methyl ester
  参考文献：
  名称：

  光中的亚硫酰香豆素和喹诺酮类化合物触发了模型氨基酸的释放：合成和光解研究

  摘要：

  通过相应的羰基前体的硫代反应，制备带有带有硫代羰基杂环的模型氨基酸酯共轭物（硫香豆素和硫喹诺酮），目的是在更长的波长下获得具有更高光敏性的共轭物。在光化学反应器（250、300、350和419 nm）中，在不同波长的辐射下进行了光解研究，结果发现，亚硫代类似物中杂环与模型氨基酸之间的酯键在较短的辐射下容易裂解。倍于相应的前体。此外，硫喹诺酮酯缀合物（在几分钟之内）在419 nm处的快速光解特别令人感兴趣，并且一些报道的杂环显示出非常不同的照射时间这一事实，可能提供在另一光可裂解基团存在下选择性除去一个基团的可能性。（喹啉-2-硫酮-4-基）甲基可以被认为是羧酸的光可裂解保护基家族的新的且非常有效的添加。

  DOI：

  10.1016/j.tet.2012.07.021
• 作为产物：
  描述：

  4-氯甲基-7-甲基色烯-2-酮 、 N-苄氧羰基-L-苯丙氨酸 在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到N-benzyloxycarbonyl-L-phenylalanine (7-methylcoumarin-4-yl)methyl ester
  参考文献：
  名称：

  Light-induced cleavage of model phenylalanine conjugates based on coumarins and quinolones

  摘要：

  In order to evaluate the application of quinolone as a new photocleavable protecting group, in comparison with coumarin, a series of model phenylalanine conjugates were prepared by reaction with chloromethylated O and N heterocycles. The photophysical properties of the resulting ester conjugates were evaluated as well as the photosensitivity under irradiation at 250, 300, 350, and 419 nm. The results obtained showed that the quinolone conjugates were readily photolysed, with complete release of the amino acid in short irradiation times and could be considered a new addition to the family of photocleavable protecting groups for the carboxylic acid function of amino acids.

  DOI：

  10.1007/s00726-010-0492-8

文献信息

• Thionated coumarins and quinolones in the light triggered release of a model amino acid: synthesis and photolysis studies
  作者：Andrea S.C. Fonseca、Ana M.S. Soares、M. Sameiro T. Gonçalves、Susana P.G. Costa

  DOI：10.1016/j.tet.2012.07.021

  日期：2012.9

  Model amino acid ester conjugates bearing heterocycles with a thiocarbonyl group (thiocoumarins and thioquinolones) were prepared by a thionation reaction of the corresponding carbonyl precursors, with the aim of obtaining conjugates with higher photosensitivity at longer wavelengths. Photolysis studies were carried out under irradiation at different wavelengths in a photochemical reactor (250, 300

  通过相应的羰基前体的硫代反应，制备带有带有硫代羰基杂环的模型氨基酸酯共轭物（硫香豆素和硫喹诺酮），目的是在更长的波长下获得具有更高光敏性的共轭物。在光化学反应器（250、300、350和419 nm）中，在不同波长的辐射下进行了光解研究，结果发现，亚硫代类似物中杂环与模型氨基酸之间的酯键在较短的辐射下容易裂解。倍于相应的前体。此外，硫喹诺酮酯缀合物（在几分钟之内）在419 nm处的快速光解特别令人感兴趣，并且一些报道的杂环显示出非常不同的照射时间这一事实，可能提供在另一光可裂解基团存在下选择性除去一个基团的可能性。（喹啉-2-硫酮-4-基）甲基可以被认为是羧酸的光可裂解保护基家族的新的且非常有效的添加。
• Light-induced cleavage of model phenylalanine conjugates based on coumarins and quinolones
  作者：Andrea S. C. Fonseca、M. Sameiro T. Gonçalves、Susana P. G. Costa

  DOI：10.1007/s00726-010-0492-8

  日期：2010.8

  In order to evaluate the application of quinolone as a new photocleavable protecting group, in comparison with coumarin, a series of model phenylalanine conjugates were prepared by reaction with chloromethylated O and N heterocycles. The photophysical properties of the resulting ester conjugates were evaluated as well as the photosensitivity under irradiation at 250, 300, 350, and 419 nm. The results obtained showed that the quinolone conjugates were readily photolysed, with complete release of the amino acid in short irradiation times and could be considered a new addition to the family of photocleavable protecting groups for the carboxylic acid function of amino acids.