6-carbomethoxy-6-hydroxy-1-methoxy-1,4-cyclohexadiene | 141040-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-carbomethoxy-6-hydroxy-1-methoxy-1,4-cyclohexadiene
• 英文别名: 6-carbomethoxy-1-methoxy-1,4-cyclohexadien-6-ol；Methyl 1-hydroxy-2-methoxycyclohexa-2,5-diene-1-carboxylate
• CAS: 141040-28-0
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: RNUBVHRNRVHVOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-carbomethoxy-6-hydroxy-1-methoxy-1,4-cyclohexadiene 在 叔丁基过氧化氢 、 重铬酸吡啶 、 Celite 作用下， 以 苯 为溶剂， 反应 2.0h， 以77%的产率得到4-carbomethoxy-4-hydroxy-3-methoxy-2,5-cyclohexadien-1-one
  参考文献：
  名称：

  Asymmetric oxidations of enolates derived from Birch reduction of methyl 2-methoxybenzoate and (S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene

  摘要：

  DOI：

  10.1021/jo00036a046
• 作为产物：
  描述：

  methyl 2-methoxycyclohexa-2,5-dienecarboxylate 在 双(三甲基硅烷基)氨基钾 、 间氯过氧苯甲酸 作用下， 生成 6-carbomethoxy-6-hydroxy-1-methoxy-1,4-cyclohexadiene
  参考文献：
  名称：

  Asymmetric oxidations of enolates derived from Birch reduction of methyl 2-methoxybenzoate and (S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene

  摘要：

  DOI：

  10.1021/jo00036a046

文献信息

• Substituent effects on the photorearrangements of 4-alkoxy-4-carbomethoxy-3-methoxy-2,5-cyclohexadien-1-ones
  作者：Arthur G. Schultz、Roger E. Harrington

  DOI：10.1021/jo00022a033

  日期：1991.10

  Enantiomerically enriched 4-carbomethoxy-3,4-dimethoxy-2,5-cyclohexadien-1-one (1) undergoes a completely diastereoselective (but not enantiospecific) type A photorearrangement at 366 nm to give 6-carbomethoxy-4,6-dimethoxybicyclo[3.1.0(1,5)]hex-3-en-2-one (2) in 81% isolated yield. A chiral NMR shift study indicates that 1 undergoes partial loss of absolute configuration at C(4) during irradiation. Bicyclohexenone 2 is photostable at 366 nm but rearranges to its diastereoisomer 3 and phenols 4 and 5 at > 300 nm. It is proposed that ground-state conformational effects control the type A photoreactivity of 1 and that rearrangement to 2 occurs in accord with the principle of least motion in the transition states for rearrangements to diastereomerically related zwitterions 1a and 1b (Scheme III). The intramolecular 2 + 2 photocycloaddition of 4-carbomethoxy-3-methoxy-4-(1'-oxa-3'-butenyl)-2,5-cyclohexadien-1-one (9) gives a mixture of 7-oxatricyclodecenones 10 (58%) and 11 (18%), without interference from type A photoreactivity.
• Asymmetric oxidations of enolates derived from Birch reduction of methyl 2-methoxybenzoate and (S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene
  作者：Arthur G. Schultz、Roger E. Harrington、Mark A. Holoboski

  DOI：10.1021/jo00036a046

  日期：1992.5