4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol | 913300-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol
• CAS: 913300-18-2
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: FWONPSSMNXXIGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到3-hydroxy-4-methyl-2-(1,2,2-trimethylcyclopentyl)phenyl acetate
  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：

  4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol dimethyl ether 在 甲基碘化镁 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 以64%的产率得到4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol
  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