ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylate | 14872-53-8

• 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: ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylate
• 英文别名: 2-ethoxycarbonyl-4-methylbutanolide；2-ethoycarbonyl-4-pentanolide；5-methyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester；5-Methyl-2-oxo-tetrahydro-furan-3-carbonsaeure-aethylester；2-Ethoxycarbonyl-4-pentanolide；ethyl 5-methyl-2-oxooxolane-3-carboxylate
• CAS: 14872-53-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: BMRQCRGDGDIHKE-UHFFFAOYSA-N

物化性质

• 沸点：
  108 °C(Press: 1.4 Torr)
• 密度：
  1.1271 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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 5-methyl-2-oxotetrahydrofuran-3-carboxylate 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 2-chloroformylmethyl-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：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Condensation of Ethyl Cyanoacetate with Alkene Oxides

  摘要：

  DOI：

  10.1021/ja01222a034

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。
• Re₂O₇/HReO₄ Mediated Intramolecular Hydroacyloxylation of Unactivated Alkenes: A Dual Hydrogen-Bonding Effect
  作者：Yibing Liu、Liqun Hu、Yuzhu Zheng、Xiong Fang、Youwei Xie

  DOI：10.1021/acs.orglett.2c03846

  日期：2023.1.13

  challenging intramolecular hydroacyloxylation reaction. Both HFIP and an internal carboxy group have been proven to be crucial for the successful implementation of this transformation; these are proposed to assist the formation and stabilization of the key cationic intermediate via hydrogen-bonding interactions with perrhenate anion (ReO4–).

  该出版物描述了 Re 2 O 7在六氟异丙醇 (HFIP) 中的应用，用于活化惰性和电子失活的烯烃，以促进具有挑战性的分子内加氢酰氧基化反应。HFIP 和内部羧基均已被证明对于成功实施这一转变至关重要；这些被提议通过与高铼酸盐阴离子 (ReO 4 – )的氢键相互作用来帮助关键阳离子中间体的形成和稳定。
• A new olefin synthesis. Synchronous elimination of nitro and ester groups or nitro and keto groups from .beta.-nitro esters or .beta.-nitro ketones
  作者：Noboru Ono、Rui Tamura、Hiromichi Eto、Isami Hamamoto、Tamon Nakatsuka、Junichi Hayami、Aritsune Kaji

  DOI：10.1021/jo00169a012

  日期：1983.10
• 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.
• 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.