(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-(allyloxy)-3-methylbenzofuran | 132802-72-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-(allyloxy)-3-methylbenzofuran
• 英文别名: (2S,3S)-2-(3,4-dimethoxyphenyl)-3-methyl-6-prop-2-enoxy-5-prop-2-enyl-2,3-dihydro-1-benzofuran
• CAS: 132802-72-3
• 化学式: C₂₃H₂₆O₄
• 分子量: 366.457
• InChiKey: HDUMMANZBRPSMI-WNSKOXEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-(allyloxy)-3-methylbenzofuran 在 四(三苯基膦)钯 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-hydroxy-3-methylbenzofuran
  参考文献：
  名称：

  Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives

  摘要：

  Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative. The yield of product in this electrochemical oxidation depends upon the ratio of phenol to styrene derivative, current density, and to a lesser extent the amount of supporting electrolyte. While p-methoxyphenol and 4-methoxy-3-methylphenol give good yields of the dihydrobenzofurans using 1:1 molar ratio of reactants, 3,4-dimethoxyphenol requires a 3-4 molar excess of the styrene derivative for a comparable yield of product. Although 4-methoxy-1-naphthol shows yields comparable to p-methoxyphenol in the anodic cycloaddition reaction, 1- and 2-naphthol gave very low yields of product. Qualitatively, trans- and cis-1,2-dimethoxy-4-propenylbenzene show similar yields in the cycloaddition reaction. Many of these same substrates were examined using iodobenzene bis(trifluoroacetate) as oxidant, and the same products were formed as in the electrochemical oxidations noted above. However, for the reaction of 2-naphthol and 1,2-dimethoxy-4-propenylbenzene the iodobenzene bis(trifluoroacetate) oxidation gave a much better yield of the product. A mechanism involving reaction of a phenoxy radical-styrene radical cation pair is considered and discussed.

  DOI：

  10.1021/jo00033a040
• 作为产物：
  描述：

  1-(allyloxy)-3-(tert-butyldimethylsiloxy)benzene 在 氯化二乙基铝 sodium methylate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙腈 为溶剂， 生成 (+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-allyl-6-(allyloxy)-3-methylbenzofuran
  参考文献：
  名称：

  A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols

  摘要：

  Oxidation of p-methoxy-substituted phenols with iodobenzene bis-trifluoroacetate in the presence of electron-rich styrene derivatives affords trans-dihydrobenzofurans stereoselectively.

  DOI：

  10.1021/jo00006a003

文献信息

• WANG, SHAOPENG;GATES, BRADLEY D.;SWENTON, JOHN S., J. ORG. CHEM. , 56,(1991) N, C. 1979-1981
  作者：WANG, SHAOPENG、GATES, BRADLEY D.、SWENTON, JOHN S.

  DOI：——

  日期：——