5-methyl-3-(prop-2-yn-1-yl)tetrahydrofuran-2-one | 1174396-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-methyl-3-(prop-2-yn-1-yl)tetrahydrofuran-2-one
• 英文别名: 5-methyl-3-(prop-2-yn-1-yl)oxolan-2-one
• CAS: 1174396-64-5
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: BZAUOPICNSXDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(prop-2-yn-1-yl)tetrahydrofuran-2-one 在 硫酸 、 水 、 mercury(II) sulfate 作用下， 反应 6.0h， 以73%的产率得到Dihydro-5-methyl-3-(2-oxopropyl)-2(3H)-furanon
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130
• 作为产物：
  描述：

  ethyl 5-methyl-2-oxo-3-(prop-2-yn-1-yl)tetrahydrofuran-3-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 以73%的产率得到5-methyl-3-(prop-2-yn-1-yl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130

文献信息

• Sonogashira reaction of 5-substituted 3-(prop-2-yn-1-yl)oxolan-2-ones
  作者：T. V. Ghochikyan、M. A. Samvelyan、A. S. Galstyan、A. Gevorgyan、G. Vardanyan、T. Grigoryan、P. Langer

  DOI：10.1134/s1070428017120089

  日期：2017.12

  Palladium-catalyzed cross-coupling of 5-methyl- and 5,5-dimethyl-3-(prop-2-yn-1-yl)oxolan-2-ones with dihaloarenes (dihaloheteroarenes) gave mixtures of the corresponding mono- and bis-coupling products. The latter can be obtained as the major products by variation of the catalytic system.

  钯催化的5-甲基-和5,5-二甲基-3-（prop-2-yn-1-基）氧杂戊-2-酮与二卤代芳烃（二卤代杂芳烃）的交叉偶联反应得到相应的单-和双耦合产品。后者可以通过改变催化体系而作为主要产物获得。