(4-chlorophenoxymethyl)-1,4-hydroquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4-chlorophenoxymethyl)-1,4-hydroquinone
• 英文别名: 2-[(4-Chlorophenoxy)methyl]benzene-1,4-diol
• 化学式: C₁₃H₁₁ClO₃
• 分子量: 250.682
• InChiKey: SEGCQNRMVJTECU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-chlorophenoxymethyl)-1,4-hydroquinone 以 甲醇 为溶剂， 生成 甲基苯醌
  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
• 作为产物：
  描述：

  2,5-bis(tert-butyldimethylsilanyloxy)-3-(4-chlorophenoxymethyl)benzene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以88%的产率得到(4-chlorophenoxymethyl)-1,4-hydroquinone
  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

• 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.