Acetic acid 5-(6-hydroxy-2,3-dimethoxy-phenyl)-2-methylene-pentyl ester | 192124-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Acetic acid 5-(6-hydroxy-2,3-dimethoxy-phenyl)-2-methylene-pentyl ester
• CAS: 192124-80-4
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: JMHCJRJPGRCBRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 Acetic acid 5-(6-hydroxy-2,3-dimethoxy-phenyl)-2-methylene-pentyl ester 在 Ti⁽³⁺⁾*NO₃^(1-) 、 碳酸氢钠 作用下， 反应 0.5h， 以66%的产率得到2-(4-acetoxymethylpent-4-enyl)-3,4,4-trimethoxycyclohexa-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
• 作为产物：
  描述：

  3,4-dimethoxy-2-(4-methylpent-4-enyl)phenoxytetrahydropyran 在 正丁基锂 、 草酸 、 碳酸氢钠 、 间氯过氧苯甲酸 、 2,2,4,4-tetramethylpiperidine 作用下， 以 吡啶 、 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 反应 32.02h， 生成 Acetic acid 5-(6-hydroxy-2,3-dimethoxy-phenyl)-2-methylene-pentyl ester
  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