(2E,2'E)-dimethyl 3,3'-(2,3-benzofurandiyl)bispropenoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2E,2'E)-dimethyl 3,3'-(2,3-benzofurandiyl)bispropenoate
• 英文别名: methyl (E)-3-[2-[(E)-3-methoxy-3-oxoprop-1-enyl]-1-benzofuran-3-yl]prop-2-enoate
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: CLUFDKDRXZTQTL-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-苯并呋喃 、 丙烯酸甲酯（MA） 在 palladium diacetate 叔丁基过氧化氢 、 乙酸酐 、 对苯醌 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以56%的产率得到(2E)-methyl 3-(2-benzofuranyl)propenoate
  参考文献：
  名称：

  Highly Efficient Pd-Catalyzed Coupling of Arenes with Olefins in the Presence of tert-Butyl Hydroperoxide as Oxidant

  摘要：

  [GRAPHICS]ArH : benzoid and non-benzoid. R = H, CH3, Ph. R-1 = Ph, Co2Et, COMe, CHO, CO2H, CN.The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins, The reaction is highly regio- and stereoselective, giving trans-olefins predominantly.

  DOI：

  10.1021/ol991148u

文献信息

• Highly Efficient Pd-Catalyzed Coupling of Arenes with Olefins in the Presence of <i>tert</i>-Butyl Hydroperoxide as Oxidant
  作者：Chengguo Jia、Wenjun Lu、Tsugio Kitamura、Yuzo Fujiwara

  DOI：10.1021/ol991148u

  日期：1999.12.1

  [GRAPHICS]ArH : benzoid and non-benzoid. R = H, CH3, Ph. R-1 = Ph, Co2Et, COMe, CHO, CO2H, CN.The oxidative coupling of arenes with olefins has been performed efficiently in the presence of catalytic amounts of palladium acetate and benzoquinone (BQ) with tert-butyl hydroperoxide as the oxidant in up to 280 turnover numbers (TON). The catalytic system is especially active for the coupling of heterocycles such as furans and indole with activated olefins, The reaction is highly regio- and stereoselective, giving trans-olefins predominantly.