3-(5-methyl-2-furyl)propyl propargyl ether | 158502-99-9

• 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)propyl propargyl ether
• CAS: 158502-99-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: DGIXVNURGGYDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(5-methyl-2-furyl)propyl propargyl ether 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 以70%的产率得到3-(5-methyl-2-furyl)propyl allenyl ether
  参考文献：
  名称：

  Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers: High Effect of the Chain Length on the Structure and Reactivity of the Cycloadducts

  摘要：

  The structure and reactivity of the cycloadducts of the title reaction were found to be highly dependent on the chain length between the furan diene and the allenyl ether dienophile. Reaction of the propargyl ether (2) with t-BuOK in t-BuOH at 85-degrees-C for 3 h gave a mixture of the cycloadducts (3) and (4) in 90% yield, which were transferred to the benzo derivatives (5), (6) and (7). Treatment of the propargyl ether (8) with t-BuoK in t-BuOH at 85-degrees-C for 5 h gave the products (9) and (10) in a ratio of 8:1 in 65% yield, no detectable amount of the cycloadduct (8b) was obtained. Refluxing of the propargyl ether (13) with t-BuOK in t-BuOH at 85-degrees-C for 4 h gave the allenyl ether (14). Heating 14 in DMSO at 15-degrees-C for 12 h still did not give 15.

  DOI：

  10.3987/com-94-6675
• 作为产物：
  描述：

  5-甲基呋喃-2-丙醛 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 3.83h， 生成 3-(5-methyl-2-furyl)propyl propargyl ether
  参考文献：
  名称：

  Intramolecular Diels-Alder Reaction of Furans with Allenyl Ethers: High Effect of the Chain Length on the Structure and Reactivity of the Cycloadducts

  摘要：

  The structure and reactivity of the cycloadducts of the title reaction were found to be highly dependent on the chain length between the furan diene and the allenyl ether dienophile. Reaction of the propargyl ether (2) with t-BuOK in t-BuOH at 85-degrees-C for 3 h gave a mixture of the cycloadducts (3) and (4) in 90% yield, which were transferred to the benzo derivatives (5), (6) and (7). Treatment of the propargyl ether (8) with t-BuoK in t-BuOH at 85-degrees-C for 5 h gave the products (9) and (10) in a ratio of 8:1 in 65% yield, no detectable amount of the cycloadduct (8b) was obtained. Refluxing of the propargyl ether (13) with t-BuOK in t-BuOH at 85-degrees-C for 4 h gave the allenyl ether (14). Heating 14 in DMSO at 15-degrees-C for 12 h still did not give 15.

  DOI：

  10.3987/com-94-6675