3-(3-methyl-3-butenyl)-1,3-dihydro-2-benzofuran-1-ol | 242462-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3-(3-methyl-3-butenyl)-1,3-dihydro-2-benzofuran-1-ol
• 英文别名: 1-Isobenzofuranol, 1,3-dihydro-3-(3-methyl-3-butenyl)-；3-(3-methylbut-3-enyl)-1,3-dihydro-2-benzofuran-1-ol
• CAS: 242462-82-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: YPDWGFPIDZDRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-(3-methyl-3-butenyl)-1,3-dihydro-2-benzofuran-1-ol 在 Montmorillonite K₁₀ 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 7.0h， 以71.7 mg的产率得到10-Methyl-13-oxa-tricyclo[8.2.1.0^2,7]trideca-2,4,6,8-tetraene
  参考文献：
  名称：

  The First Example of (2,5) Ene Cyclization:  Solid Acid-Catalyzed Oxonium-Ene Reaction

  摘要：

  Among the six different types of intramolecular ene reactions (ene cyclizations), the (2,5) ene cyclization has never been reported. The first example of the (2,5) intramolecular ene reaction is exploited involving oxonium ion as an intermediate. The cyclization is efficiently catalyzed by solid acids such as montmorillonite K10 to organize the (2,5) oxonium-ene reaction in preference to (2,4) (Oppolzer's type II) in the mesopore of the solid acids. This regiochemical fidelity is consistent with the direct conversion of oxonium ion to the (2,5) ene product via an intramolecular ene pathway involving the hydrogen shift of the methyl protons with close proximity in the mesopore of K10.

  DOI：

  10.1021/jo990682c

文献信息

• The First Example of (2,5) Ene Cyclization:  Solid Acid-Catalyzed Oxonium-Ene Reaction
  作者：Hirofumi Ohmura、Gyles Darren Smyth、Koichi Mikami

  DOI：10.1021/jo990682c

  日期：1999.8.1

  Among the six different types of intramolecular ene reactions (ene cyclizations), the (2,5) ene cyclization has never been reported. The first example of the (2,5) intramolecular ene reaction is exploited involving oxonium ion as an intermediate. The cyclization is efficiently catalyzed by solid acids such as montmorillonite K10 to organize the (2,5) oxonium-ene reaction in preference to (2,4) (Oppolzer's type II) in the mesopore of the solid acids. This regiochemical fidelity is consistent with the direct conversion of oxonium ion to the (2,5) ene product via an intramolecular ene pathway involving the hydrogen shift of the methyl protons with close proximity in the mesopore of K10.