trans-1,5-dihydroxy-2,6-dimethoxy-1-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene

• 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: trans-1,5-dihydroxy-2,6-dimethoxy-1-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene
• 英文别名: (7R,8R)-8-(2,3-dimethoxyphenyl)-2,7-dimethoxybicyclo[4.2.0]octa-1(6),2,4-triene-3,8-diol
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: PHUOAQQAHCHIFN-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-1,5-dihydroxy-2,6-dimethoxy-1-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene 在 palladium on activated charcoal 氢气 作用下， 生成 trans-4-hydroxy-1,3-dimethoxy-2-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene 、 cis-4-hydroxy-1,3-dimethoxy-2-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene
  参考文献：
  名称：

  基于光化学的立体选择性进入某些酚反式2-芳基苯并环丁烯醇甲基醚

  摘要：

  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。

  DOI：

  10.1016/0040-4039(91)80871-3
• 作为产物：
  描述：

  3-hydroxy-6-(methoxymethyl)-2,2',3'-trimethoxybenzophenone 以 四氢呋喃 为溶剂， 以70%的产率得到trans-1,5-dihydroxy-2,6-dimethoxy-1-(2',3'-dimethoxyphenyl)dihydrobenzocyclobutene
  参考文献：
  名称：

  基于光化学的立体选择性进入某些酚反式2-芳基苯并环丁烯醇甲基醚

  摘要：

  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。

  DOI：

  10.1016/0040-4039(91)80871-3

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.