2,3,4-呋喃三羧酸三乙酯 | 7251-41-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,3,4-呋喃三羧酸三乙酯
• 英文名称: 2-ethyl 3,4-diethyl 2,3,4-furantricarboxylate
• 英文别名: triethyl furan-2,3,4-tricarboxylate；furan-2,3,4-tricarboxylic acid triethyl ester；Furan-2,3,4-tricarbonsaeure-triaethylester
• CAS: 7251-41-4
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: AGTTVMJPDZPRJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  175-180 °C(Press: 3 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  2-ethyl 3,4-diethyl 4-bromo-4,5-dihydro-2,3,4-furantricarboxylate 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到2,3,4-呋喃三羧酸三乙酯
  参考文献：
  名称：

  Efficient synthesis of 2,3,4-trisubstituted furans from the reaction of activated acetylenes with ethyl bromopyruvate in the presence of enaminones

  摘要：

  The reaction of dialkyl acetylenedicarboxylates or diaroylacetylenes with ethyl bromopyruvate in the presence of enaminones led to 2-ethyl 3,4-dialkyl 4-bromo-4,5-dihydro-2,3,4-furantricarboxylates or ethyl 3,4-diaroyl-4-bromo-4,5-dihydro-2-furancarboxylate in excellent yields. These compounds are quantitatively converted to the corresponding 2,3,4-trisubstituted furans by 4-dimethylaminopyridine.

  DOI：

  10.1007/s00706-008-0858-8

文献信息

• THE SYNTHESIS OF FURAN, THIOPHENE, AND PYRROLE-3,4-DICARBOXYLIC ESTERS
  作者：E. C. KORNFELD、R. G. JONES

  DOI：10.1021/jo01375a017

  日期：1954.10
• 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.
• Furan-polycarbonsäuren
  作者：T. Reichstein、A. Grüssner、K. Schindler、E. Hardmeier

  DOI：10.1002/hlca.19330160138

  日期：——
• JAWORSKI T.; MIZERSKI T., ROCZ. CHEM. <ROCH-AC>, 1976, 50, NO 2, 359-362
  作者：JAWORSKI T.、 MIZERSKI T.

  DOI：——

  日期：——
• Efficient synthesis of 2,3,4-trisubstituted furans from the reaction of activated acetylenes with ethyl bromopyruvate in the presence of enaminones
  作者：Issa Yavari、Zinatossadat Hossaini、Maryam Sabbaghan

  DOI：10.1007/s00706-008-0858-8

  日期：2008.8

  The reaction of dialkyl acetylenedicarboxylates or diaroylacetylenes with ethyl bromopyruvate in the presence of enaminones led to 2-ethyl 3,4-dialkyl 4-bromo-4,5-dihydro-2,3,4-furantricarboxylates or ethyl 3,4-diaroyl-4-bromo-4,5-dihydro-2-furancarboxylate in excellent yields. These compounds are quantitatively converted to the corresponding 2,3,4-trisubstituted furans by 4-dimethylaminopyridine.