3-(5-methyl-2-furyl)allyl acetate | 132376-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(5-methyl-2-furyl)allyl acetate
• 英文别名: 3-acetoxy-1t-(5-methyl-[2]furyl)-propene；3-Acetoxy-1t-(5-methyl-[2]furyl)-propen；[(E)-3-(5-methylfuran-2-yl)prop-2-enyl] acetate
• CAS: 132376-63-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: PCCCQPDIKGFAHT-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-methyl-2-furyl)allyl acetate 在 bis-triphenylphosphine-palladium(II) chloride 一氧化碳 、 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 170.0 ℃ 、6.86 MPa 条件下， 反应 1.5h， 以76%的产率得到4-Acetoxy-2-methylbenzofuran
  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：

  5-甲基呋喃醛 在 4-二甲氨基吡啶 、 sodium 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 29.0h， 生成 3-(5-methyl-2-furyl)allyl 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

文献信息

• Ponomarew; Lipanowa, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1719,1724; engl. Ausg. S. 1811, 1814
  作者：Ponomarew、Lipanowa

  DOI：——

  日期：——
• Synthesis of benzofurans and benzothiophenes by palladium catalyzed cyclocarbonylation of 3-furylallyl and 3-thienylallyl acetates
  作者：Masakazu Iwasaki、Ji-ping Li、Yoshihiro Kobayashi、Hiroyuki Matsuzaka、Youichi Ishii、Masanobu Hidai

  DOI：10.1016/s0040-4039(01)80332-4

  日期：——
• IWASAKI, MASAKAZU;KOBAYASHI, YOSHIHIRO;LI, JI-PING;MATSUZAKA, HIROYUKI;IS+, J. ORG. CHEM., 56,(1991) N, C. 1922-1927
  作者：IWASAKI, MASAKAZU、KOBAYASHI, YOSHIHIRO、LI, JI-PING、MATSUZAKA, HIROYUKI、IS+

  DOI：——

  日期：——
• IWASAKI, MASAKAZU;LI, JI-PING;KOBAYASHI, YOSHIHIRO;MATSUZAKA, HIROYUKI;IS+, TETRAHEDRON LETT., 30,(1989) N 1, C. 95-98
  作者：IWASAKI, MASAKAZU、LI, JI-PING、KOBAYASHI, YOSHIHIRO、MATSUZAKA, HIROYUKI、IS+

  DOI：——

  日期：——