α-bromo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester | 1233875-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-bromo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester
• 英文别名: allyl 2-bromo-2-(4,5-dimethoxy-2-nitrophenyl)acetate；Prop-2-enyl 2-bromo-2-(4,5-dimethoxy-2-nitrophenyl)acetate
• CAS: 1233875-87-0
• 化学式: C₁₃H₁₄BrNO₆
• 分子量: 360.161
• InChiKey: OURDAOBJBQELNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-bromo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (1S)-2-(4-(2-(allyloxy)-1-(4,5-dimethoxy-2-nitrophenyl)-2-oxoethoxy)phenyl)-1-carboxyethanaminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives

  摘要：

  报道了通过α-羧基-6-硝基藜芦基（αCNV）保护基保护在酚羟基上的光不稳定性酪氨酸衍生物的合成。这些化合物在波长大于300 nm的光照射下迅速发生光解反应，以优异的产率释放相应的苯酚（酪氨酸去保护的量子产率为0.19）。还可以对笼蔽的酪氨酸进行进一步保护，得到适合直接用于固相肽合成的N-芴甲氧羰基保护衍生物。

  DOI：

  10.1039/c2pp05320a
• 作为产物：
  描述：

  α-diazo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到α-bromo-4,5-dimethoxy-2-nitrophenylacetic acid allyl ester
  参考文献：
  名称：

  α-Carboxy-6-nitroveratryl: A Photolabile Protecting Group for Carboxylic Acids

  摘要：

  The synthesis of a new photolabile protecting group for carboxylic acids, alpha-carboxy-6-nitroveratryl (alpha CNV), is described. Bromide 3, prepared in four steps from 3,4-dimethoxyphenylacetic acid, was used to alkylate carboxylic acids under mild conditions in good yield. Palladium-catalyzed deallylation afforded the acids 4a-h, which underwent rapid and quantitative photolysis at wavelengths longer than 300 nm to liberate the carboxylic acid in good to quantitative yield. The rate of photolysis and quantum yield were determined to be 325 s(-1) and 0.17.

  DOI：

  10.1021/jo100783v

文献信息

• α-Carboxy-6-nitroveratryl: A Photolabile Protecting Group for Carboxylic Acids
  作者：Alexander G. Russell、Maria-Eleni Ragoussi、Rui Ramalho、Christopher W. Wharton、David Carteau、Dario M. Bassani、John S. Snaith

  DOI：10.1021/jo100783v

  日期：2010.7.2

  The synthesis of a new photolabile protecting group for carboxylic acids, alpha-carboxy-6-nitroveratryl (alpha CNV), is described. Bromide 3, prepared in four steps from 3,4-dimethoxyphenylacetic acid, was used to alkylate carboxylic acids under mild conditions in good yield. Palladium-catalyzed deallylation afforded the acids 4a-h, which underwent rapid and quantitative photolysis at wavelengths longer than 300 nm to liberate the carboxylic acid in good to quantitative yield. The rate of photolysis and quantum yield were determined to be 325 s(-1) and 0.17.
• Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives
  作者：Alexander G. Russell、Matthew J. Sadler、Helen J. Laidlaw、Agustín Gutiérrez-Loriente、Christopher W. Wharton、David Carteau、Dario M. Bassani、John S. Snaith

  DOI：10.1039/c2pp05320a

  日期：2012.3

  The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.

  报道了通过α-羧基-6-硝基藜芦基（αCNV）保护基保护在酚羟基上的光不稳定性酪氨酸衍生物的合成。这些化合物在波长大于300 nm的光照射下迅速发生光解反应，以优异的产率释放相应的苯酚（酪氨酸去保护的量子产率为0.19）。还可以对笼蔽的酪氨酸进行进一步保护，得到适合直接用于固相肽合成的N-芴甲氧羰基保护衍生物。