2-Methyl-4,5-dimethoxy-benzylalkohol | 90926-82-2

• 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-Methyl-4,5-dimethoxy-benzylalkohol
• 英文别名: (4,5-Dimethoxy-2-methylphenyl)methanol
• CAS: 90926-82-2
• 化学式: C₁₀H₁₄O₃
• mdl: MFCD08443198
• 分子量: 182.219
• InChiKey: LXXMVMUOOPRTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methyl-4,5-dimethoxy-benzylalkohol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以1.9 g的产率得到1-(氯甲基)-4,5-二甲氧基-2-甲基苯
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of an Antifungal Tricyclic o-Hydroxy-p-Quinone Methide Diterpenoid

  摘要：

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.

  DOI：

  10.1021/jo4013964
• 作为产物：
  描述：

  4,5-dimethoxy-2-methylbenzoic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-Methyl-4,5-dimethoxy-benzylalkohol
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of an Antifungal Tricyclic o-Hydroxy-p-Quinone Methide Diterpenoid

  摘要：

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.

  DOI：

  10.1021/jo4013964

文献信息

• Electrochemical Generation and Reaction of <i>o</i>-Quinodimethanes from {[[2-(2,2-Dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes
  作者：Madoka Jinno、Yoshikazu Kitano、Masahiro Tada、Kazuhiro Chiba

  DOI：10.1021/ol990647s

  日期：1999.8.1

  The anodic oxidation of [[2-(2,2-dibutyl-2-stannahexyl)phenyl]methyl]thio}benzenes gave o-quinodimethanes which were trapped in situ by dienophiles to give the corresponding cycloadducts in excellent yields. The electron transfer and succeeding 1,4-elimination reaction was efficiently completed in a solution of lithium perchlorate/nitromethane in the presence of acetic acid. The reaction progress was quantitatively controlled by the passage of charge. By using this new method, an aryltetralin lignan skeleton was also synthesized.
• Total Synthesis and Biological Evaluation of an Antifungal Tricyclic <i>o</i>-Hydroxy-<i>p</i>-Quinone Methide Diterpenoid
  作者：Jinhua Huang、Dylan Foyle、Xiaorong Lin、Jiong Yang

  DOI：10.1021/jo4013964

  日期：2013.9.20

  A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and ana- logues. A Li/naphthalene-mediated reductive alkylation was employed for coupling beta-cyclocitral and the corresponding benzyl chloride, while a BBr3- mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure activity relationship of the diterpenoid was assessed on the basis of antiproliferation assays of the natural product and analogues against strains of pathogenic yeasts and filamentous fungi.