dimethyl 6-hydroxy-1(1,2-cis),5-dimethoxy-4-(3,4-trans)(2'-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-trans-dicarboxylate | 143925-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: dimethyl 6-hydroxy-1(1,2-cis),5-dimethoxy-4-(3,4-trans)(2'-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-trans-dicarboxylate
• CAS: 143925-91-1
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: ORXBKZCAEQKLIR-OJAHFUOMSA-N

物化性质

• 沸点：
  539.6±50.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4-hydroxy-1,3-dimethoxy-2-(2'-methoxyphenyl)dihydrobenzocyclobutene 、 富马酸二甲酯 以 甲苯 为溶剂， 反应 5.0h， 以40%的产率得到dimethyl 6-hydroxy-1(1,2-cis),5-dimethoxy-4-(3,4-trans)(2'-methoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-trans-dicarboxylate
  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