4-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enol | 913300-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enol
• 英文别名: 4-(2,6-Dimethoxy-3-methylphenyl)-4-methylcyclopent-2-en-1-ol
• CAS: 913300-11-5
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: GDFLYYDQOAMLAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  4-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到4-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enone
  参考文献：
  名称：

  Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4

  摘要：

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.062
• 作为产物：
  描述：

  2,4-二甲氧基甲苯 在 Grubbs catalyst first generation lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 silica gel 、 丙酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 127.42h， 生成 4-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enol
  参考文献：
  名称：

  Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4

  摘要：

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.062