triethyl 5-methylfuran-2,3,4-tricarboxylate | 23127-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: triethyl 5-methylfuran-2,3,4-tricarboxylate
• 英文别名: Triethyl 5-methylfuran-2,3,4-tricarboxylate
• CAS: 23127-62-0
• 化学式: C₁₄H₁₈O₇
• 分子量: 298.293
• InChiKey: WCMZJVOBWPDGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丁炔二酸二乙酯 、 2-氯乙酰乙酸乙酯 在 三乙烯二胺 、 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 1.5h， 以80%的产率得到triethyl 5-methylfuran-2,3,4-tricarboxylate
  参考文献：
  名称：

  Synthesis of furan-2,3,4-tricarboxylate in biphasic water–Et2O solvent system

  摘要：

  The reaction of dialkyl acetylenedicarboxylates with ethyl bromopyruvate or alpha-chlorocarbonyl compounds in the presence of 1,4-diazabicyclo[2.2.2]octane led to furan-2,3,4-tricarboxylates or the related 2-acetylfuran-3,4-dicarboxylates in excellent yield.

  DOI：

  10.1007/s10593-015-1778-2

文献信息

• Facile Strategy for the Synthesis of Furans Utilizing Silver(I)-Promoted Addition/Oxidative Cyclization of 1,3-Dicarbonyl Compounds and Alkynoates
  作者：Wei-Bing Liu、Cui Chen、Qing Zhang

  DOI：10.1080/00397911.2011.615102

  日期：2013.3.1

  Abstract The addition/oxidative cyclization of alkynoates with 1,3-dicarbonyl compounds in the presence of Ag(I) leads to polysubstituted furans. The reaction corresponds to the construction of a furan fragment, which also provides a new way to form the C-O bond. GRAPHICAL ABSTRACT

  摘要 在 Ag(I) 存在下，炔酸酯与 1,3-二羰基化合物的加成/氧化环化产生多取代呋喃。该反应对应于呋喃片段的构建，这也为形成 CO 键提供了新的途径。图形概要
• A chemoselective rhodium(II) mediated solid phase 1,3-dipolar cycloaddition and its application to a thermally self-cleaving furan scaffold
  作者：Darren L. Whitehouse、Kingsley H. Nelson、Sergey N. Savinov、David J. Austin

  DOI：10.1016/s0040-4039(97)01768-1

  日期：1997.10

  acetylenes with isomünchnones is presented as a general methodology for the combinatorial formation of a furan based library. Additionally, through the development of a novel thermolytic cleavage step, this furan synthesis yields pure product from the solid-phase in a temperature dependent manner.

  描述了在固相上化学选择性的铑（II）介导的1,3-偶极环加成反应，用于构建模板导向的支架。在本文中，提出了乙炔与异氰酸酯的反应作为呋喃基文库组合形成的一般方法。另外，通过开发新的热裂解步骤，该呋喃合成以依赖温度的方式从固相产生纯产物。
• Synthetic Approach to Polysubstituted Furans: An Efficient Addition/Oxidative Cyclization of Alkynoates and 1,3-Dicarbonyl Compounds
  作者：Weibing Liu、Huanfeng Jiang、Min Zhang、Chaorong Qi

  DOI：10.1021/jo902375k

  日期：2010.2.5

  A novel and reliable method for the direct construction of polysubstituted furans is reported. The key transformation involves Sn(II)- and Cu(I)-involved addition/oxidative cyclization of alkynoates and 1,3-dicarbonyl compounds in the presence of 2,3-dichloro-5,6-dicyano-benzoquinone.
• Synthesis of furan-2,3,4-tricarboxylate in biphasic water–Et2O solvent system
  作者：Maryam Sabbaghan、Ali Yousefi

  DOI：10.1007/s10593-015-1778-2

  日期：2015.9

  The reaction of dialkyl acetylenedicarboxylates with ethyl bromopyruvate or alpha-chlorocarbonyl compounds in the presence of 1,4-diazabicyclo[2.2.2]octane led to furan-2,3,4-tricarboxylates or the related 2-acetylfuran-3,4-dicarboxylates in excellent yield.