3-(1,2,2-trimethylcyclopentyl)-6-methylbenzene-1,2-diol | 159898-20-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(1,2,2-trimethylcyclopentyl)-6-methylbenzene-1,2-diol
• 英文别名: cuparene-1,2-diol；3-Methyl-6-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol
• CAS: 159898-20-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: GVYYOVVPKOYDIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1,2,2-trimethylcyclopentyl)-6-methylbenzene-1,2-diol 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以68%的产率得到2-hydroxy-3-(1,2,2-trimethylcyclopentyl)-6-methylphenyl 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-(2,3-dimethoxy-4-methylphenyl)-4,5,5-trimethylcyclopent-2-enone 在 palladium on activated charcoal 氢气 、 碘 、 三溴化硼 、 镍 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 3-(1,2,2-trimethylcyclopentyl)-6-methylbenzene-1,2-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

文献信息

• Total Synthesis of (+)-Aquaticol by Biomimetic Phenol Dearomatization: Double Diastereofacial Differentiation in the Diels–Alder Dimerization of Orthoquinols with aC2-Symmetric Transition State
  作者：Julien Gagnepain、Frédéric Castet、Stéphane Quideau

  DOI：10.1002/anie.200604610

  日期：2007.2.19
• Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4
  作者：A. Srikrishna、P.C. Ravikumar

  DOI：10.1016/j.tet.2006.07.062

  日期：2006.10

  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.