(E)-2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan | 234753-61-8

• 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: (E)-2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan
• 英文别名: 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan；2-(2-Vinylstyryl)benzofuran；2-[(E)-2-(2-ethenylphenyl)ethenyl]-1-benzofuran
• CAS: 234753-61-8
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: KKFCAMOXAHOCKE-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan 在 氧气 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 145.17h， 生成 11,12-dihydro-6,11-methano-12-exo-hydroxy-6H-benzo[4,5]cyclohepta[1,2-b]benzo[d]furan
  参考文献：
  名称：

  Observation of the Primary Intermediates in the Photochemistry of o-Vinylstyrylfurans

  摘要：

  DOI：

  10.3987/com-01-9314
• 作为产物：
  描述：

  聚合甲醛 、 苯并[b]呋喃-2-甲醛 、 o-xylylene(bistriphenylphospine) dibromide 在 sodium ethanolate 作用下， 以81%的产率得到(E)-2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan
  参考文献：
  名称：

  Synthesis and Photochemistry of Styryl Substituted Annelated Furan Derivatives

  摘要：

  New beta-substituted benzo- and naphthofuryl derivatives (5, 6 and 7) of o-divinylbenzene, were synthesized and irradiated in order to form annelated bicyclo[3.2.1]octadienes. While 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (5) upon irradiation gives the bicyclo[3.2.1]octadiene derivative (12) in 65% yield, 2-[2-(2-vinylphenyl) ethenyl]naphtho[2,1-b]furan (6) and 2-[2-(2-vinylphenyl)ethenyl]naphtho[1,2-b]furan (7), undergo cis-trans-isomerization but not form intramolecular photocycloaddition products. The mechanism of the intramolecular [2+2] photocycloaddition is explained via intermediate (17) which was proved by the formation of products (18) and (19), by irradiation in methanol and deuteromethanol.

  DOI：

  10.3987/com-99-8502

文献信息

• Synthesis and Photochemistry of Styryl Substituted Annelated Furan Derivatives
  作者：Marija Sindler-Kulyk、Irena Skoric、Slavica Tomsic、Zeljko Marinic、Draginja Mrvos-Sermek

  DOI：10.3987/com-99-8502

  日期：——

  New beta-substituted benzo- and naphthofuryl derivatives (5, 6 and 7) of o-divinylbenzene, were synthesized and irradiated in order to form annelated bicyclo[3.2.1]octadienes. While 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (5) upon irradiation gives the bicyclo[3.2.1]octadiene derivative (12) in 65% yield, 2-[2-(2-vinylphenyl) ethenyl]naphtho[2,1-b]furan (6) and 2-[2-(2-vinylphenyl)ethenyl]naphtho[1,2-b]furan (7), undergo cis-trans-isomerization but not form intramolecular photocycloaddition products. The mechanism of the intramolecular [2+2] photocycloaddition is explained via intermediate (17) which was proved by the formation of products (18) and (19), by irradiation in methanol and deuteromethanol.
• Observation of the Primary Intermediates in the Photochemistry of o-Vinylstyrylfurans
  作者：Marija Sindler-Kulyk、Irena Skoric、Nikola Basaric、Zeljko Marinic

  DOI：10.3987/com-01-9314

  日期：——