[(2S,3R)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methyl acetate | 593245-52-4

• 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: [(2S,3R)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methyl acetate
• CAS: 593245-52-4
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: LQAQCYHSTUAPJQ-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methyl acetate 在 吡啶 、 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  铁（III）催化反应与酶促反应相结合的策略合成旋光的2,3-二氢苯并呋喃衍生物

  摘要：

  光学活性的2，3-二氢呋喃衍生物的合成是通过铁离子催化的苯乙烯衍生物与醌的环加成反应以及脂肪酶催化的对映选择性酰化反应的结合策略而完成的。

  DOI：

  10.1016/s0040-4039(03)00843-8
• 作为产物：
  描述：

  乙酸乙烯酯 、 (+/-)-trans-[5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-3-yl]methanol 在 异丙醚 作用下， 生成 [(2S,3R)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]methyl acetate
  参考文献：
  名称：

  Development of Solvent-Driven Iron-Catalyzed Reactions

  摘要：

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.

  DOI：

  10.3987/rev-16-842