(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-methoxy-3-methylbenzofuran | 132802-66-5

• 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-methoxy-3-methylbenzofuran
• 英文别名: 2-(3,4-dimethoxyphenyl)-5-methoxy-3-methyl-2,3-dihydrobenzofuran；(2S,3S)-2-(3,4-dimethoxyphenyl)-5-methoxy-3-methyl-2,3-dihydro-1-benzofuran
• CAS: 132802-66-5
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: ZDARKRFMVFTQCY-VOJFVSQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-1,2-二甲氧基-4-(1-丙烯基)苯 、 4-甲氧基苯酚 在 ammonium peroxydisulfate 作用下， 以 硝基甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(+/-)-trans-2-(3,4-dimethoxyphenyl)-2,3-dihydro-5-methoxy-3-methylbenzofuran
  参考文献：
  名称：

  共价三嗪骨架纳米粒子通过尺寸可控的限制合成增强可见光光氧化还原催化。

  摘要：

  对于无金属有机共轭聚合物基光催化剂，合成确定的纳米结构仍然具有很大的挑战性。在这里，我们报告了通过尺寸可控的限制聚合策略形成共价三嗪骨架 (CTF) 纳米粒子。与不规则的块状材料相比，均匀的 CTF 纳米粒子在二苯并呋喃的光催化形成中表现出显着增强的活性。通过将少量苯并噻二唑共聚到共轭分子网络中，可以轻松调节纳米级 CTF 的光电特性。这种电子特性的优化导致观察到的光催化效率进一步提高，与块状材料相比，总共提高了 18 倍。

  DOI：

  10.1002/anie.202007358

文献信息

• Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols
  作者：Travis R. Blum、Ye Zhu、Sarah A. Nordeen、Tehshik P. Yoon

  DOI：10.1002/anie.201406393

  日期：2014.10.6

  We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible‐light‐activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled, benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis

  我们报告了苯酚和烯烃的氧化[3+2]环加成反应方案，适用于一大类二氢苯并呋喃天然产物的模块化合成。可见光激活的过渡金属光催化使得过硫酸铵成为一种易于处理的良性末端氧化剂。很容易被光氧化还原催化氧化的有机底物范围广泛，表明该策略可能适用于各种有用的氧化转化。
• Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives
  作者：Bradley D. Gates、Peter Dalidowicz、Andrew Tebben、Shaopeng Wang、John S. Swenton

  DOI：10.1021/jo00033a040

  日期：1992.3

  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.
• A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols
  作者：Shaopeng Wang、Bradley D. Gates、John S. Swenton

  DOI：10.1021/jo00006a003

  日期：1991.3

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