2,4-dimethoxy-1-phenoxybenzene | 1071966-05-6

• 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: 2,4-dimethoxy-1-phenoxybenzene
• CAS: 1071966-05-6
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: SSIQLIRVZLGHGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-1-phenoxybenzene 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以80%的产率得到苯酚
  参考文献：
  名称：

  2,4-二甲氧基苯基甲基保护的醇和羧酸的其他无亲核性FeCl3催化绿色脱保护。

  摘要：

  甲氧基苯基甲基（MPM）醚和酯衍生物的脱保护通常可以通过催化路易斯酸和化学计量亲核试剂的组合使用来实现。发现2，4-二甲氧基苯基甲基（DMPM）保护的醇和羧酸的脱保护可被氯化铁（III）有效地催化，而无需任何其他亲核试剂以优异的产率形成脱保护的母醇和羧酸。由于本脱保护反应是通过2,4-DMPM保护基自身的自组装机理进行的，从而得到了难溶的间苯二甲烯衍生物，为沉淀物，因此不需要通过硅胶柱色谱法进行严格的纯化，而且需要足够的纯度。简单过滤后，很容易以令人满意的收率获得醇和羧酸。

  DOI：

  10.1248/cpb.c16-00161
• 作为产物：
  描述：

  2,4-二甲氧基溴苯 、 苯酚 反应 7.0h， 以31%的产率得到2,4-dimethoxy-1-phenoxybenzene
  参考文献：
  名称：

  Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis

  摘要：

  Aucuparin is the most widely distributed biphenyl phytoalexin in the rosaceous subtribe Pyrinae, which includes the economically important fruit trees apple and pear. The biphenyl scaffold is formed by biphenyl synthase, which catalyzes biosynthesis of 3,5-dihydroxybiphenyl. Conversion of this precursor to aucuparin (3,5-dimethoxy-4-hydroxybiphenyl) was studied in cell cultures of Sorbus aucuparia after treatment with an elicitor preparation from the scab-causing fungus Venturia inaequalis. The sequence of the biosynthetic steps detected was O-methylation - 4-hydroxylation - O-methylation. The two alkylation reactions were catalyzed by distinct methyltransferases, which differed in pH and temperature optima as well as stability. Biphenyl 4-hydroxylase was a microsomal cytochrome P450 monooxygenase, whose activity was appreciably decreased by the addition of established P450 inhibitors. When fed to V. inaequalis-treated S. aucuparia cell cultures, radioactively labeled 3,5-dihydroxybiphenyl was not only incorporated into aucuparin but also into the dibenzofuran eriobofuran, the accumulation of which paralleled that of aucuparin. However, biphenyl 2'-hydroxylase activity proposed to be involved in dibenzofuran formation was detected in neither microsomes nor cell-free extracts in the presence of NADPH and 2-oxoglutarate, respectively. Nevertheless, a basis for studying biphenyl biosynthesis at the gene level is provided. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.003

文献信息

• US3963753A
  申请人：——

  公开号：US3963753A

  公开（公告）日：1976-06-15
• Additional Nucleophile-Free FeCl<sub>3</sub>-Catalyzed Green Deprotection of 2,4-Dimethoxyphenylmethyl-Protected Alcohols and Carboxylic Acids
  作者：Yoshinari Sawama、Masahiro Masuda、Akie Honda、Hiroki Yokoyama、Kwihwan Park、Naoki Yasukawa、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1248/cpb.c16-00161

  日期：——

  mother alcohols and carboxylic acids in excellent yields. Since the present deprotection proceeds via the self-assembling mechanism of the 2,4-DMPM protective group itself to give the hardly-soluble resorcinarene derivative as a precipitate, the rigorous purification process by silica-gel column chromatography was unnecessary and the sufficiently-pure alcohols and carboxylic acids were easily obtained

  甲氧基苯基甲基（MPM）醚和酯衍生物的脱保护通常可以通过催化路易斯酸和化学计量亲核试剂的组合使用来实现。发现2，4-二甲氧基苯基甲基（DMPM）保护的醇和羧酸的脱保护可被氯化铁（III）有效地催化，而无需任何其他亲核试剂以优异的产率形成脱保护的母醇和羧酸。由于本脱保护反应是通过2,4-DMPM保护基自身的自组装机理进行的，从而得到了难溶的间苯二甲烯衍生物，为沉淀物，因此不需要通过硅胶柱色谱法进行严格的纯化，而且需要足够的纯度。简单过滤后，很容易以令人满意的收率获得醇和羧酸。
• Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis
  作者：Mohammed N.A. Khalil、Till Beuerle、Andreas Müller、Ludger Ernst、Vijaya B.R. Bhavanam、Benye Liu、Ludger Beerhues

  DOI：10.1016/j.phytochem.2013.09.003

  日期：2013.12

  Aucuparin is the most widely distributed biphenyl phytoalexin in the rosaceous subtribe Pyrinae, which includes the economically important fruit trees apple and pear. The biphenyl scaffold is formed by biphenyl synthase, which catalyzes biosynthesis of 3,5-dihydroxybiphenyl. Conversion of this precursor to aucuparin (3,5-dimethoxy-4-hydroxybiphenyl) was studied in cell cultures of Sorbus aucuparia after treatment with an elicitor preparation from the scab-causing fungus Venturia inaequalis. The sequence of the biosynthetic steps detected was O-methylation - 4-hydroxylation - O-methylation. The two alkylation reactions were catalyzed by distinct methyltransferases, which differed in pH and temperature optima as well as stability. Biphenyl 4-hydroxylase was a microsomal cytochrome P450 monooxygenase, whose activity was appreciably decreased by the addition of established P450 inhibitors. When fed to V. inaequalis-treated S. aucuparia cell cultures, radioactively labeled 3,5-dihydroxybiphenyl was not only incorporated into aucuparin but also into the dibenzofuran eriobofuran, the accumulation of which paralleled that of aucuparin. However, biphenyl 2'-hydroxylase activity proposed to be involved in dibenzofuran formation was detected in neither microsomes nor cell-free extracts in the presence of NADPH and 2-oxoglutarate, respectively. Nevertheless, a basis for studying biphenyl biosynthesis at the gene level is provided. (C) 2013 Elsevier Ltd. All rights reserved.