4-chloromethyl-1-methylquinolin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-chloromethyl-1-methylquinolin-2(1H)-one
• 英文别名: 4-chloromethyl-1-methyl-1H-quinolin-2-one；4-Chlormethyl-1-methyl-1H-chinolin-2-on；N-Methyl-4-chlormethyl-2-chinolon；4-(chloromethyl)-1-methylquinolin-2-one
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: MKVNTYGLLWTMFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloromethyl-1-methylquinolin-2(1H)-one 、 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91%的产率得到N-benzyloxycarbonyl-L-phenylalanine (1-methylquinolin-2(1H)-one-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
• 作为产物：
  描述：

  4-(羟基甲基)-1-甲基-2(1H)-喹啉酮 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到4-chloromethyl-1-methylquinolin-2(1H)-one
  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

• The Reaction between o-Aminoazo Compounds and Barbituric Acid. A New Synthesis of Riboflavin
  作者：Max Tishler、Karl Pfister、R. D. Babson、Kurt Ladenburg、Ann J. Fleming

  DOI：10.1021/ja01198a068

  日期：1947.6
• 1-Methyl-4-carbostyrilcarboxaldehyde and Certain Condensation Products
  作者：D. J. Cook、Martha Stamper

  DOI：10.1021/ja01198a063

  日期：1947.6
• 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.