N-(benzyloxycarbonyl)-L-valine (9-methoxy-3-thioxo-3H-benzo[f]benzopyran-1-yl)methyl ester | 1395394-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: N-(benzyloxycarbonyl)-L-valine (9-methoxy-3-thioxo-3H-benzo[f]benzopyran-1-yl)methyl ester
• CAS: 1395394-06-5
• 化学式: C₂₈H₂₇NO₆S
• 分子量: 505.591
• InChiKey: ZZTGWSNWVQYCBE-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-L-valine (9-methoxy-3-thioxo-3H-benzo[f]benzopyran-1-yl)methyl ester 以 甲醇 为溶剂， 反应 0.5h， 生成 CBZ-L-缬氨酸
  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：

  1-chloromethyl-9-methoxy-3-oxo-3H-benzo[f]benzopyran 在 劳森试剂 、 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 N-(benzyloxycarbonyl)-L-valine (9-methoxy-3-thioxo-3H-benzo[f]benzopyran-1-yl)methyl ester
  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