4-(2,6-dimethoxy-3-methylphenyl)-4,5,5-trimethylcyclopent-2-enone | 913300-13-7

• 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: 4-(2,6-dimethoxy-3-methylphenyl)-4,5,5-trimethylcyclopent-2-enone
• CAS: 913300-13-7
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: SZXVYJCFBZKHCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2,6-dimethoxy-3-methylphenyl)-4,5,5-trimethylcyclopent-2-enone 在 palladium on activated charcoal 咪唑 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 8.33h， 生成 4-methyl-2-(1,2,2-trimethylcyclopentyl)benzene-1,3-diol dimethyl ether
  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-(2,6-dimethoxy-3-methylphenyl)-4-methylcyclopent-2-enone 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以73%的产率得到4-(2,6-dimethoxy-3-methylphenyl)-4,5,5-trimethylcyclopent-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