4-(tert-butoxycarbonylamino)butyric acid α-allyloxycarbonyl-4,5-dimethoxy-2-nitrobenzyl ester | 1233876-03-3

• 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: 4-(tert-butoxycarbonylamino)butyric acid α-allyloxycarbonyl-4,5-dimethoxy-2-nitrobenzyl ester
• 英文别名: [1-(4,5-Dimethoxy-2-nitrophenyl)-2-oxo-2-prop-2-enoxyethyl] 4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1233876-03-3
• 化学式: C₂₂H₃₀N₂O₁₀
• 分子量: 482.488
• InChiKey: HTTCOGVHRCGVEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-(tert-butoxycarbonylamino)butyric acid α-allyloxycarbonyl-4,5-dimethoxy-2-nitrobenzyl ester 、 三氟乙酸 在 四(三苯基膦)钯 、 甲酸 、 三正丁胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以64%的产率得到2-(4-Aminobutanoyloxy)-2-(4,5-dimethoxy-2-nitrophenyl)acetic acid;2,2,2-trifluoroacetic acid
  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
• 作为产物：
  描述：

  N-BOC-GAMMA-氨基丁酸 、 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 0.5h， 以76%的产率得到4-(tert-butoxycarbonylamino)butyric acid α-allyloxycarbonyl-4,5-dimethoxy-2-nitrobenzyl 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.