3,4,4-trimethoxy-6-methyl-2-(4-methylpent-4-enyl)cyclohexa-2,5-dienone | 192124-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,4-trimethoxy-6-methyl-2-(4-methylpent-4-enyl)cyclohexa-2,5-dienone
• 英文别名: 3,4,4-Trimethoxy-6-methyl-2-(4-methylpent-4-enyl)cyclohexa-2,5-dien-1-one
• CAS: 192124-46-2
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: HNURJYIJXLIBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,4-trimethoxy-6-methyl-2-(4-methylpent-4-enyl)cyclohexa-2,5-dienone 在 三氟甲磺酸三甲基硅酯 、 lithium perchlorate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.08h， 以90%的产率得到(3α,7β,8aβ)-5-methoxy-7,8a-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：

  2-羟基-4,5-二甲氧基甲苯 在 六甲基磷酰三胺 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 草酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 3,4,4-trimethoxy-6-methyl-2-(4-methylpent-4-enyl)cyclohexa-2,5-dienone
  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

文献信息

• 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
  作者：P Grieco*

  DOI：10.1016/s0040-4020(97)00581-4

  日期：1997.6.30

  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.