methyl 4-hydroxy-6-(2',4'-dimethoxybenzoyl)-5-methoxybenzoate | 143925-88-6

• 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: methyl 4-hydroxy-6-(2',4'-dimethoxybenzoyl)-5-methoxybenzoate
• 英文别名: Methyl 2-(2,4-dimethoxybenzoyl)-4-hydroxy-3-methoxybenzoate
• CAS: 143925-88-6
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: NSUNOGQYFGTZEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲氧基-4-(甲基乙基)苯酚 在 正丁基锂 、 氧气 、 铬酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 7.17h， 生成 methyl 4-hydroxy-6-(2',4'-dimethoxybenzoyl)-5-methoxybenzoate
  参考文献：
  名称：

  Stereoselective photocyclization of some phenolic, highly congested benzophenones and benzaldehydes. Use of cis-2-arylbenzocyclobutenol methyl ethers for the synthesis of lignans

  摘要：

  Irradiation of some highly congested, phenolic 2-(methoxymethyl)benzophenones provides a rapid, efficient and stereoselective entry to the corresponding 1-aryl-1-hydroxy-2-methoxybenzocyclobutenes in high chemical yield. The analogous photocyclization reaction of phenolic benzaldehydes appears to be more limited in scope. According to semiempirical (AM1) calculations on the thermal ring opening of a large number of benzocyclobutene derivatives, alpha,alpha'-dioxygenated o-quinodimethanes are significantly more stable (5-7 kcal/mol) than the corresponding benzocyclobutene derivatives, thereby suggesting that 1-hydroxy-2-alkoxybenzocyclobutenes are unlikely to be thermally derived from the corresponding o-QDM's during photolysis of o-(methoxymethyl)benzophenones. Hydrogenolysis (H-2, Pd/C) of either the cis or trans isomers of 1-aryl-1-hydroxy-2-methoxybenzocyclobutenes gives rise to cis-trans mixtures of 1-methoxy-2-arylbenzocyclobutenes enriched in the cis isomer. These enriched mixtures undergo thermal isomerization to the desired trans 1-methoxy-2-arylbenzocyclobutenes. The cis-enriched mixture directly derived from the hydrogenolysis step can be used as a precursor of the required (E,E)-alpha-aryl-alpha'-methoxy-o-quinodimethane for the synthesis of lignanes via the intermolecular Diels-Alder approach.

  DOI：

  10.1021/jo00049a033

文献信息

• Stereoselective photocyclization of some phenolic, highly congested benzophenones and benzaldehydes. Use of cis-2-arylbenzocyclobutenol methyl ethers for the synthesis of lignans
  作者：Gloria Coll、Antoni Costa、Pere M. Deya、Francina Flexas、Carmen Rotger、Jose M. Saa

  DOI：10.1021/jo00049a033

  日期：1992.11

  Irradiation of some highly congested, phenolic 2-(methoxymethyl)benzophenones provides a rapid, efficient and stereoselective entry to the corresponding 1-aryl-1-hydroxy-2-methoxybenzocyclobutenes in high chemical yield. The analogous photocyclization reaction of phenolic benzaldehydes appears to be more limited in scope. According to semiempirical (AM1) calculations on the thermal ring opening of a large number of benzocyclobutene derivatives, alpha,alpha'-dioxygenated o-quinodimethanes are significantly more stable (5-7 kcal/mol) than the corresponding benzocyclobutene derivatives, thereby suggesting that 1-hydroxy-2-alkoxybenzocyclobutenes are unlikely to be thermally derived from the corresponding o-QDM's during photolysis of o-(methoxymethyl)benzophenones. Hydrogenolysis (H-2, Pd/C) of either the cis or trans isomers of 1-aryl-1-hydroxy-2-methoxybenzocyclobutenes gives rise to cis-trans mixtures of 1-methoxy-2-arylbenzocyclobutenes enriched in the cis isomer. These enriched mixtures undergo thermal isomerization to the desired trans 1-methoxy-2-arylbenzocyclobutenes. The cis-enriched mixture directly derived from the hydrogenolysis step can be used as a precursor of the required (E,E)-alpha-aryl-alpha'-methoxy-o-quinodimethane for the synthesis of lignanes via the intermolecular Diels-Alder approach.