乙基5,5-二甲基-2-羰基四氢呋喃-3-羧酸酯 | 14668-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 乙基5,5-二甲基-2-羰基四氢呋喃-3-羧酸酯
• 英文名称: ethyl 5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate
• 英文别名: 2-ethoycarbonyl-4-methyl-4-pentanolide；5,5-dimethyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester；5,5-Dimethyl-2-oxo-tetrahydro-furan-3-carbonsaeure-aethylester；α-Carbethoxy-γ,γ-dimethyl-γ-butyrolacton；4-Ethoxycarbonyl-2,2-dimethyl-5-oxo-tetrahydrofuran；Ethyl 5,5-dimethyl-2-oxooxolane-3-carboxylate
• CAS: 14668-39-4
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: ZBLCRMTYDQGIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  乙基5,5-二甲基-2-羰基四氢呋喃-3-羧酸酯 在 sodium hydroxide 、 氯化亚砜 、 水 、 sodium 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 4-methyl-2-(1-thiosemicarbazidocarbonyl)-4-pentanolide
  参考文献：
  名称：

  摘要：

  Alkylation of 2-ethoxycarbonyl-4-pentanol ides with ethyl chloroacetate gave 2-ethoxycarbonyl-2 ethoxycarbonylmethyl-4-pentanolides. Alkaline hydrolysis of the latter afforded 2-carboxymethyl-4-pentanolides which were converted into the corresponding acyl chlorides in high yield by treatment with thionyl chloride in the presence of a catalytic amount of dimethylformamide. Reaction of 2-chloroformylmethyl-4-pentanolides with thiosemicarbazide, followed by treatment with alkali, resulted in formation of 2-(5-mercapto-1,2,4-triazol-3-ylmethyl)-4-pentanolides.

  DOI：

  10.1023/a:1016338226670
• 作为产物：
  描述：

  diethyl 2,2-dimethylcyclopropane-1,1-dicarboxylate 在 高氯酸 作用下， 反应 6.0h， 以87%的产率得到乙基5,5-二甲基-2-羰基四氢呋喃-3-羧酸酯
  参考文献：
  名称：

  Improved Synthesis of γ-Lactones from Cyclopropyl Cyanoesters

  摘要：

  [image omitted] Cyclopropyl cyanoesters 2 were reliably converted to -lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint.

  DOI：

  10.1080/00397911.2010.501472

文献信息

• Efficient synthesis of triazole-containing spiro dilactones
  作者：Tariel V. Ghochikyan、Vasily M. Muzalevskiy、Melanya A. Samvelyan、Armen S. Galstyan、Valentine G. Nenajdenko

  DOI：10.1016/j.mencom.2016.01.005

  日期：2016.1

  3-ethoxycarbonyltetrahydrofuran-2-ones. Subsequent conversion of the bromomethyl group into azidomethyl one followed by click reaction with alkynes afforded the multifunctional triazole-containing spiro dilactones in almost quantitative yields.

  从3-乙氧基羰基四氢呋喃-2-酮可有效制备3-溴甲基-2,8-二氧杂螺[4.4]壬烷-1,6-二酮。随后将溴甲基基团转化为叠氮基甲基基团，然后与炔烃进行点击反应，以几乎定量的产率得到了含多功能三唑的螺二内酯。
• Transition Metal-Free Intermolecular C(sp²)–H Direct Amination of Furanones via a Redox Pathway
  作者：Qiang Wei、Junfeng Wang、Eman A. Akam、Dawei Yin、Zemei Ge、Tieming Cheng、Xin Wang、Anna-Liisa Brownell、Runtao Li

  DOI：10.1021/acs.joc.8b02760

  日期：2019.2.1

  A direct C(sp2)–H amination of 2-furanones under metal-free conditions was realized. This unprecedented intermolecular C–H to C–N conversion provides rapid access to 4-amino-furanone derivatives and novel aza-heterocycle fused furanone skeletons. A redox mechanism based on a double-Michael-addition intermediate INT2 is proposed and detected by spectrometry.

  在无金属条件下实现了2-呋喃酮的直接C（sp 2）-H胺化反应。前所未有的分子间C–H到C–N的转化为快速获得4-氨基呋喃酮衍生物和新颖的氮杂杂环稠合呋喃酮骨架提供了便利。提出了基于双迈克尔加成中间体INT2的氧化还原机理，并通过光谱法对其进行了检测。
• 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.
• Condensation of Ethyl Cyanoacetate with Alkene Oxides
  作者：Samuel A. Glickman、Arthur C. Cope

  DOI：10.1021/ja01222a034

  日期：1945.6
• Synthesis of 2‐Ethoxycarbonyl‐2‐Bromo‐4‐Methyl‐4‐Substituted Butanolides and New Spiroheteryl‐Joint Butanolides Based Thereon
  作者：Tariel Kochikyan

  DOI：10.1081/scc-200036633

  日期：2004.12.31

  The bromination reaction of 2-ethoxycarbonyl-4-methyl-4-substituted butanolides has been studied, and it has been established that bromination with equimolar quantity of bromine in dry carbon tetrachloride was obtained in good yields of 2-ethoxycarbonyl-2-bromo-4-methyl-4-substituted butanolides. The interaction of the latter with thiourea and substituted thioureas has been investigated. It has been shown that under conditions of Hunch's reaction, as a result of heterocyclization were obtained spiroheteryl joint lactones of a new generation-2-aza-3-amino or substituted amino-4-thia-7-oxa-8-methyl-8-substituted spiro[4,4]-2-, nonene-1,6-diones.