L-phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester hydrobromide | 1341226-33-2

• 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: L-phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester hydrobromide
• 英文别名: L-phenylalanine (9-methoxy-3-oxo-3Hbenzo[f]benzopyran-1-yl)methyl ester hydrobromide
• CAS: 1341226-33-2
• 化学式: BrH*C₂₄H₂₁NO₅
• 分子量: 484.346
• InChiKey: MMECUFIEEVGGHH-BDQAORGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  L-phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester hydrobromide 以 甲醇 为溶剂， 反应 8.67h， 生成 L-苯丙氨酸
  参考文献：
  名称：

  Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates

  摘要：

  Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3-benzo[]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3-benzo[]benzopyran--valine and -phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage data were obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths.

  DOI：

  10.1007/s00726-011-0969-0
• 作为产物：
  描述：

  N-(benzyloxycarbonyl) phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester 在 氢溴酸 、 溶剂黄146 作用下， 反应 72.0h， 以61%的产率得到L-phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester hydrobromide
  参考文献：
  名称：

  Photorelease of amino acids from novel thioxobenzo[f]benzopyran ester conjugates

  摘要：

  Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3-benzo[]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3-benzo[]benzopyran--valine and -phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage data were obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths.

  DOI：

  10.1007/s00726-011-0969-0

文献信息

• Long-Wavelength Photolysis of Amino Acid 6-(Methoxy-2-oxo-2H-naphtho[1,2-b]pyran-4-yl)methyl Esters
  作者：Ana M. Piloto、Ana M. S. Soares、Graham Hungerford、Susana P. G. Costa、M. Sameiro T. Gonçalves

  DOI：10.1002/ejoc.201100391

  日期：2011.10

  phenylalanine as model bifunctional molecules were synthesised to assess its applicability as a photocleavable protecting group for solution phase organic synthesis and in caging applications at longer wavelengths. The behaviour of the corresponding derivatives towards photolysis was evaluated by irradiation at 350 and 419 nm in a mixture of HEPES buffer and acetonitrile or methanol in a photochemical reactor

  合成了缬氨酸或苯丙氨酸的 (6-Methoxy-2-oxo-2H-naphtho[1,2-b]pyran-4-yl) 甲酯作为模型双功能分子，以评估其作为溶液相有机物的光裂解保护基团的适用性合成和在更长波长的笼形应用中。相应衍生物对光解的行为通过在光化学反应器中的 HEPES 缓冲液和乙腈或甲醇的混合物中以 350 和 419 nm 的辐射进行评估，然后进行 HPLC/UV 监测。时间分辨荧光测量用于阐明动力学。