2,5-dimethoxybenzyl benzoate | 138250-68-7

• 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: 2,5-dimethoxybenzyl benzoate
• 英文别名: (2,5-Dimethoxyphenyl)methyl benzoate
• CAS: 138250-68-7
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: CEHCXAGXVAWSHO-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  397.4±27.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxybenzyl benzoate 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到对二甲氧基苯甲醇
  参考文献：
  名称：

  使用镁和甲醇对酯进行选择性脱保护

  摘要：

  描述了在甲醇中使用金属镁使烷基酯脱保护。这种温和的试剂还具有很好的选择性，可以裂解不同的酯。发现该试剂对酰基裂解的反应性顺序为：对硝基苯甲酸酯>乙酸酯>苯甲酸酯>新戊酸酯>三氟乙酰胺。

  DOI：

  10.1016/s0040-4039(00)73392-2
• 作为产物：
  描述：

  对二甲氧基苯甲醇 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到2,5-dimethoxybenzyl benzoate
  参考文献：
  名称：

  2,5-Dihydroxybenzyl and (1,4-Dihydroxy-2-naphthyl)methyl, Novel Reductively Armed Photocages for the Hydroxyl Moiety

  摘要：

  [Graphics]Irradiation of alcohols, phenols, and carboxylic acids "caged" with the 2,5-dihydroxybenzyl group or its naphthalene analogue results in the efficient release of the substrate. The initial byproduct of the photoreaction, 4-hydroxyquinone-2-methide, undergoes rapid tautomerization into methyl p-quinone. The UV spectrum of the latter is different from that of the caging chromophore, thus permitting selective irradiation of the starting material in the presence of photochemical products. These photoremovable protecting groups can be armed in situ by the reduction of photochemically inert p-quinone precursors.

  DOI：

  10.1021/jo701426j

文献信息

• Selective deprotection of esters using magnesium and methanol
  作者：Yao-Chang Xu、Elaine Lebeau、Clint Walker

  DOI：10.1016/s0040-4039(00)73392-2

  日期：1994.8

  The use of magnesium metal in methanol for the deprotection of alkyl esters is described. This mild reagent also provides good to excellent selectivity to cleave different esters. The order of the reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate > acetate > benzoate > pivaloate > trifluroacetamide.

  描述了在甲醇中使用金属镁使烷基酯脱保护。这种温和的试剂还具有很好的选择性，可以裂解不同的酯。发现该试剂对酰基裂解的反应性顺序为：对硝基苯甲酸酯>乙酸酯>苯甲酸酯>新戊酸酯>三氟乙酰胺。
• Xu Yao-Chang, Lebeau Elaine, Walker Clint, Tetrahedron Lett, 35 (1994) N 34, S 6207-6210
  作者：Xu Yao-Chang, Lebeau Elaine, Walker Clint

  DOI：——

  日期：——
• 2,5-Dihydroxybenzyl and (1,4-Dihydroxy-2-naphthyl)methyl, Novel Reductively Armed Photocages for the Hydroxyl Moiety
  作者：Alexey P. Kostikov、Vladimir V. Popik

  DOI：10.1021/jo701426j

  日期：2007.11.1

  [Graphics]Irradiation of alcohols, phenols, and carboxylic acids "caged" with the 2,5-dihydroxybenzyl group or its naphthalene analogue results in the efficient release of the substrate. The initial byproduct of the photoreaction, 4-hydroxyquinone-2-methide, undergoes rapid tautomerization into methyl p-quinone. The UV spectrum of the latter is different from that of the caging chromophore, thus permitting selective irradiation of the starting material in the presence of photochemical products. These photoremovable protecting groups can be armed in situ by the reduction of photochemically inert p-quinone precursors.
• Selective deprotection of alkyl esters using magnesium methoxide
  作者：Xu Yao-Chang、Amsalu Bizuneh、Clint Walker

  DOI：10.1016/0040-4039(95)02197-3

  日期：1996.1

  The use of magnesium methoxide for the deprotection of alkyl esters is described. This mild reagent provides a good method to cleave esters efficiently and more importantly, allows for effective differentiation between two different esters. The order of the reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate>acetate>benzoate>pivaloate>>acetamide.

  描述了使用甲醇镁使烷基酯脱保护。这种温和的试剂提供了一种有效裂解酯的好方法，更重要的是，它可以有效区分两种不同的酯。发现该试剂对酰基裂解的反应性顺序为：对硝基苯甲酸酯>乙酸酯>苯甲酸酯>新戊酸酯>>乙酰胺。