trans-4-hydroxy-1,3-dimethoxy-2-(2'-methoxyphenyl)dihydrobenzocyclobutene | 133387-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: trans-4-hydroxy-1,3-dimethoxy-2-(2'-methoxyphenyl)dihydrobenzocyclobutene
• 英文别名: (7R,8S)-2,7-dimethoxy-8-(2-methoxyphenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-ol
• CAS: 133387-08-3；133387-11-8
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: RZFFLNCSEHKCIN-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-甲氧基-4-(甲基乙基)苯酚 在 palladium on activated charcoal 正丁基锂 、 氢气 、 铬酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~25.0 ℃ 、227.53 kPa 条件下， 反应 11.17h， 生成 trans-4-hydroxy-1,3-dimethoxy-2-(2'-methoxyphenyl)dihydrobenzocyclobutene
  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

• A photochemically-based stereoselective entry to some phenolic trans 2-arylbenzocyclobutenol methyl ethers
  作者：Gloria Coll、Antoni Costa、Pere M. Deyá、José M. Saá

  DOI：10.1016/0040-4039(91)80871-3

  日期：1991.1

  efficiently provided the corresponding benzocyclobutenols , in a highly stereoselective manner. These compounds on hydrogenolysis and subsequent heating furnished trans-2-arylbenzocyclobutenol methyl ethers .

  几种3-羟基-2-甲氧基-6-甲氧基甲基二苯甲酮的光化学激发以高度立体选择性的方式有效地提供了相应的苯并环丁烯醇。这些化合物在氢解和随后的加热下提供了反式-2-芳基苯并环丁烯醇甲基醚。