ethyl 3-benzyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate | 1129542-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-benzyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate
• 英文别名: Ethyl 3-benzyl-5,5-dimethyl-2-oxotetrahydro-3-furancarboxylate；ethyl 3-benzyl-5,5-dimethyl-2-oxooxolane-3-carboxylate
• CAS: 1129542-45-5
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: XCVYQYVEDXHTAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  37-38 °C
• 沸点：
  133-135 °C(Press: 1 Torr)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-benzyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 以83%的产率得到3-benzyl-5,5-dimethyltetrahydrofuran-2-one
  参考文献：
  名称：

  New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

  摘要：

  Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.

  DOI：

  10.1134/s1070428008060122
• 作为产物：
  描述：

  乙基5,5-二甲基-2-羰基四氢呋喃-3-羧酸酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到ethyl 3-benzyl-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

  摘要：

  Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.

  DOI：

  10.1134/s1070428008060122

文献信息

• Efficient Intramolecular Hydroarylation Catalysed by BiIII Triflate
  作者：Bastien Cacciuttolo、Sophie Poulain-Martini、Elisabet Duñach

  DOI：10.1002/ejoc.201100213

  日期：2011.7

  Non-activated aromatic compounds bearing unsaturated side-chains afford tetralin and benzosuberan derivatives in good yields in an atom-economic, environmentally friendly process catalysed by bismuth(III) trifluromethanesulfonate.

  带有不饱和侧链的未活化芳族化合物在三氟甲磺酸铋 (III) 催化的原子经济、环境友好的过程中以良好的收率提供四氢萘和苯并丁二烯衍生物。
• Access to Polycyclic Derivatives by Triflate-Catalyzed Intramolecular Hydroarylation
  作者：Bastien Cacciuttolo、Sophie Poulain-Martini、Fabien Fontaine-Vive、Mahmoud Ali Hussein Abdo、Hussein El-Kashef、Elisabet Duñach

  DOI：10.1002/ejoc.201402972

  日期：2014.11

  An efficient and versatile synthesis of indane, tetralin and benzosuberan derivatives has been developed; the synthesis starts from nonactivated aromatic compounds bearing unsaturated side chains and is a bismuth(III) or indium(III) trifluoromethanesulfonate-catalysed atom-economic process. A variety of polycyclic compounds have been isolated in high yields. Lactonisation could be observed for esters

  茚满、四氢萘和苯并舒茚衍生物的高效和多功能合成已被开发出来；该合成从带有不饱和侧链的未活化芳族化合物开始，是铋 (III) 或三氟甲磺酸铟 (III) 催化的原子经济过程。已以高产率分离出多种多环化合物。通过烯烃与酯基之一之间的路易斯酸催化反应，可以观察到具有 2,2-二取代末端烯烃的酯的内酯化。
• New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates
  作者：T. V. Kochikyan、E. V. Arutyunyan、V. S. Arutyunyan、A. A. Avetisyan

  DOI：10.1134/s1070428008060122

  日期：2008.6

  Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.