2-[Hydroxy-(4-isopropyl-7-methyl-benzofuran-2-yl)-methyl]-heptanoic acid ethyl ester | 132376-83-1

• 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: 2-[Hydroxy-(4-isopropyl-7-methyl-benzofuran-2-yl)-methyl]-heptanoic acid ethyl ester
• CAS: 132376-83-1
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: QEGQDEWXJDEAPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[Hydroxy-(4-isopropyl-7-methyl-benzofuran-2-yl)-methyl]-heptanoic acid ethyl ester 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 7.0h， 生成 (E)-3-(4-isopropyl-7-methyl-2-benzofuranyl)-2-pentylallyl acetate
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046
• 作为产物：
  描述：

  庚酸乙酯 、 4-isopropyl-7-methylbenzofuran-2-carbaldehyde 在 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-[Hydroxy-(4-isopropyl-7-methyl-benzofuran-2-yl)-methyl]-heptanoic acid ethyl ester
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046