2-(3,3-Dimethyl-pent-4-enyl)-3,4-dimethoxy-phenol | 192124-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3,3-Dimethyl-pent-4-enyl)-3,4-dimethoxy-phenol
• 英文别名: 2-(3,3-dimethylpent-4-enyl)-3,4-dimethoxyphenol
• CAS: 192124-81-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: PJDXGAKPNXMFFH-UHFFFAOYSA-N

物化性质

• 沸点：
  353.3±37.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(3,3-Dimethyl-pent-4-enyl)-3,4-dimethoxy-phenol 在 三氟甲磺酸三甲基硅酯 、 Ti⁽³⁺⁾*NO₃^(1-) 、 lithium perchlorate 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 0.58h， 生成 (3α,7β,8aβ)-5-methoxy-1,1-dimethyl-1,2,3,7,8,8a-hexahydro-3a,7-methanoazulene-4,9-dione
  参考文献：
  名称：

  INTRAMOLECULAR CATIONIC [5 + 2] CYCLOADDITION REACTIONS PROMOTED BY TRIMETHYLSILYL TRIFLATE IN 3.0 M LITHIUM PERCHLORATE-ETHYL ACETATE: APPLICATION TO A FORMAL TOTAL SYNTHESIS OF (±)-ISOCOMENE

  摘要：

  Trimethylsilyl triflate is an effective reagent in 3.0 M lithium perchlorate-ethyl acetate for promoting intramolecular cationic [5 + 2] cycloaddition reactions. A formal total synthesis of the angular triquinane isocomene (10) is detailed. Cationic [5 + 2] cycloaddition of quinone monoketal 40 gives rise to tricyclic diketone 35 which is subsequently converted into the known tricyclic ketone 33. Addition of methyl lithium followed by acid-catalyzed rearrangement employing the Pirrung protocol affords (+/-)-isocomene (10). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00581-4
• 作为产物：
  描述：

  3,4-dimethoxy-2-(3,3-dimethylpent-4-enyl)phenoxytetrahydropyran 在 草酸 作用下， 以 甲醇 、 水 为溶剂， 以99%的产率得到2-(3,3-Dimethyl-pent-4-enyl)-3,4-dimethoxy-phenol
  参考文献：
  名称：

  INTRAMOLECULAR CATIONIC [5 + 2] CYCLOADDITION REACTIONS PROMOTED BY TRIMETHYLSILYL TRIFLATE IN 3.0 M LITHIUM PERCHLORATE-ETHYL ACETATE: APPLICATION TO A FORMAL TOTAL SYNTHESIS OF (±)-ISOCOMENE

  摘要：

  Trimethylsilyl triflate is an effective reagent in 3.0 M lithium perchlorate-ethyl acetate for promoting intramolecular cationic [5 + 2] cycloaddition reactions. A formal total synthesis of the angular triquinane isocomene (10) is detailed. Cationic [5 + 2] cycloaddition of quinone monoketal 40 gives rise to tricyclic diketone 35 which is subsequently converted into the known tricyclic ketone 33. Addition of methyl lithium followed by acid-catalyzed rearrangement employing the Pirrung protocol affords (+/-)-isocomene (10). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00581-4