4-hydroxy-2,3-dimethylphenyl allyl ether | 3732-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-2,3-dimethylphenyl allyl ether
• 英文别名: 4-allyloxy-2,3-dimethylphenol；4-Allyloxy-2,3-dimethyl-phenol；2,3-Dimethyl-4-prop-2-enoxyphenol
• CAS: 3732-03-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: SHEDKPQHQHZINU-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±37.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2,3-dimethylphenyl allyl ether 在 吡啶 、 咪唑 、 sodium hydroxide 、 ozone-containing oxygen 、 三甲基锍 、 四丁基氟化铵 、 N,N-二乙基苯胺 、 三甲基乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.42h， 生成 methyl (E)-6-[2-methoxy-3,4-dimethyl-5-(trifluoromethylsulfonyloxy)phenyl]-4-methylhex-4-enoate
  参考文献：
  名称：

  Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid

  摘要：

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.

  DOI：

  10.1021/jm9603633
• 作为产物：
  描述：

  3-溴丙烯 、 2,3-二甲基氢醌 在 sodium ethanolate 作用下， 生成 4-hydroxy-2,3-dimethylphenyl allyl ether
  参考文献：
  名称：

  929.Chrom-3-en-6-ols。吡啶对烷-2-烯基-苯醌的作用

  摘要：

  DOI：

  10.1039/jr9650005060

文献信息

• 929. Chrom-3-en-6-ols. The action of pyridine on alk-2-enyl-benzoquinones
  作者：D. McHale、J. Green

  DOI：10.1039/jr9650005060

  日期：——
• Development of Novel Antioxidants:  Design, Synthesis, and Reactivity
  作者：Helmi H. Hussain、Gordana Babic、Tony Durst、James S. Wright、Mihaela Flueraru、Alexandru Chichirau、Leonid L. Chepelev

  DOI：10.1021/jo0301090

  日期：2003.9.1

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.
• Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid
  作者：Peter H. Nelson、Stephen F. Carr、Bruce H. Devens、Elsie M. Eugui、Fidencio Franco、Carlos Gonzalez、Ronald C. Hawley、David G. Loughhead、David J. Milan、Eva Papp、John W. Patterson、Sussan Rouhafza、Eric B. Sjogren、David B. Smith、Rebecca A. Stephenson、Francisco X. Talamas、Ann-Marie Waltos、Robert J. Weikert、John C. Wu

  DOI：10.1021/jm9603633

  日期：1996.1.1

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.