2,3-Dihydro-5-hydroxy-2-phenylbenzofuran | 34701-78-5

• 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: 2,3-Dihydro-5-hydroxy-2-phenylbenzofuran
• 英文别名: 2-phenyl-2,3-dihydro-benzofuran-5-ol；2,3-Dihydro-2-phenyl-5-benzofuranol；2-phenyl-2,3-dihydro-1-benzofuran-5-ol
• CAS: 34701-78-5
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: XKHGPRVEAVDYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dihydro-5-hydroxy-2-phenylbenzofuran 在 六氟异丙醇 、 碘苯二乙酸 、 2,3,4,5,6-五氟苯甲酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 2-phenyl-2,3-dihydrobenzo[1,2-b:4,5-b’]difuran
  参考文献：
  名称：

  New Synthesis of Tetrahydrobenzodifurans by Iterative Coupling of Quinone Monoacetals with Alkene Nucleophiles

  摘要：

  A new efficient synthetic strategy of tetrahydrobenzodifurans has been developed by the repetitive [3+2] couplings of quinone monoacetals with alkene nucleophiles. Both the symmetrical and unsymmetrical tetrahydrobenzodifurans can be easily synthesized by this continuous method by altering the type of alkenes. These tetrahydrobenzodifurans have also become a useful precursor of highly-substituted benzofurans by dehydrogenation.

  DOI：

  10.3987/com-15-s(t)41
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 在 六氟异丙醇 、 2,3,4,5,6-五氟苯甲酸 、 L-Selectride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 2,3-Dihydro-5-hydroxy-2-phenylbenzofuran
  参考文献：
  名称：

  New Synthesis of Tetrahydrobenzodifurans by Iterative Coupling of Quinone Monoacetals with Alkene Nucleophiles

  摘要：

  A new efficient synthetic strategy of tetrahydrobenzodifurans has been developed by the repetitive [3+2] couplings of quinone monoacetals with alkene nucleophiles. Both the symmetrical and unsymmetrical tetrahydrobenzodifurans can be easily synthesized by this continuous method by altering the type of alkenes. These tetrahydrobenzodifurans have also become a useful precursor of highly-substituted benzofurans by dehydrogenation.

  DOI：

  10.3987/com-15-s(t)41

文献信息

• Three-Component Oxyarylation of Alkenes Enables Access to C₃-Substituted Dihydrobenzofurans
  作者：Guidong Feng、Shutao Sun、Guoliang Liu、Huan Long、Lei Liu

  DOI：10.1021/acs.orglett.8b03278

  日期：2018.12.7

  A practical and modular three-component alkene oxyarylation with benzoquinone and H2O to rapidly access C-3-substituted dihydrobenzofurans has been developed. The (NH4)(2)S2O8-mediated redox-relay process has an excellent regioselectivity and functional group tolerance and exhibits a broad scope of simple alkenes, rapidly furnishing a variety of the substructures that would require multiple steps to prepare with traditional methods. Mechanistic studies revealed a dual role of benzoquinone serving as both the arylation agent and the origin of dihydroquinone for the reductive cyclization step.
• New Synthesis of Tetrahydrobenzodifurans by Iterative Coupling of Quinone Monoacetals with Alkene Nucleophiles
  作者：Yasuyuki Kita、Tohru Kamitanaka、Hitoho Takamuro、Kazuyuki Shimizu、Yudai Aramaki、Toshifumi Dohi

  DOI：10.3987/com-15-s(t)41

  日期：——

  A new efficient synthetic strategy of tetrahydrobenzodifurans has been developed by the repetitive [3+2] couplings of quinone monoacetals with alkene nucleophiles. Both the symmetrical and unsymmetrical tetrahydrobenzodifurans can be easily synthesized by this continuous method by altering the type of alkenes. These tetrahydrobenzodifurans have also become a useful precursor of highly-substituted benzofurans by dehydrogenation.