3,4-di(ethoxycarbonyl)-2,5-dioxohexanedioic acid diethyl ester | 101254-21-1

• 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
• 英文名称: 3,4-di(ethoxycarbonyl)-2,5-dioxohexanedioic acid diethyl ester
• 英文别名: 1,4-dioxo-butane-1,2,3,4-tetracarboxylic acid tetraethyl ester；1,4-Dioxo-butan-1,2,3,4-tetracarbonsaeure-tetraaethylester；Hexanedioic acid, 3,4-bis(ethoxycarbonyl)-2,5-dioxo-, diethyl ester；tetraethyl 1,4-dioxobutane-1,2,3,4-tetracarboxylate
• CAS: 101254-21-1
• 化学式: C₁₆H₂₂O₁₀
• 分子量: 374.345
• InChiKey: VWQYYHQRDRQBCY-UHFFFAOYSA-N

物化性质

• 沸点：
  485.1±45.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4-di(ethoxycarbonyl)-2,5-dioxohexanedioic acid diethyl ester 在 ammonium carbonate 、 溶剂黄146 作用下， 反应 4.0h， 以13%的产率得到tetraethyl 1H-pyrrole-2,3,4,5-tetracarboxylate
  参考文献：
  名称：

  Quantification of Naturally Occurring Pyrrole Acids in Melanosomes

  摘要：

  AbstractThree naturally occurring pyrrole acids were found in Sepia, human black hair, and bovine choroid and iris melanosomes using high‐performance liquid chromatography and mass spectrometry—pyrrole‐2,3‐dicarboxylic acid (PDCA), pyrrole‐2,3,5‐tricarboxylic acid (PTCA) and pyrrole‐2,3,4,5‐tetracarboxylic acid (PTeCA). PDCA and PTCA are common markers quantified from oxidative degradation of eumelanins. Using standards, the amounts of naturally occurring PDCA and PTCA were determined and compared to those obtained following peroxide oxidation of the same samples. Because the naturally occurring acids are water soluble, these results indicate that care must be exercised when comparing PDCA and PTCA yields from the degradation analyses of melanins isolated and prepared by different methods. This work also establishes that PTeCA is a naturally occurring pyrrole acid in melanosomes.

  DOI：

  10.1111/j.1751-1097.2008.00328.x
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以81%的产率得到3,4-di(ethoxycarbonyl)-2,5-dioxohexanedioic acid diethyl ester
  参考文献：
  名称：

  ,, ... und ehrt mir ihre Kunst!“ – Evaluierung historischer und neuer Synthesewege zu 1,5-Dihydroxy-6-oxo-1,6-dihydropyridin-2-carbonsäure und 1,3-Dihydroxy-2-oxo-3-pyrrolin-4-carbonsäure / “. . . and honour their art!” – Evaluation of Historical and New Routes to 1,5-Dihydroxy-6-oxo-1,6- dihydropyridine-2-carboxylic Acid and 1,3-Dihydroxy-2-oxo-3-pyrroline-4-carboxylic Acid

  摘要：

  „... und ehrt mir ihre Kunst!“ – 评估历史和新的合成途径到1,5-二羟基-6-酮基-1,6-二氢吡啶-2-羧酸和1,3-二羟基-2-酮基-3-吡咯烯-4-羧酸 / “. . . and honour their art!” – 评估历史和新的合成途径到1,5-二羟基-6-酮基-1,6-二氢吡啶-2-羧酸和1,3-二羟基-2-酮基-3-吡咯烯-4-羧酸

  DOI：

  10.1515/znb-2009-11-1206

文献信息

• Blaise; Gault, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1908, vol. 147, p. 200
  作者：Blaise、Gault

  DOI：——

  日期：——
• Vitale et al., Rendiconto dell'Accademia delle Scienze Fisiche e Matematiche, Naples, 1959, vol. <4> 26, p. 267,269
  作者：Vitale et al.

  DOI：——

  日期：——
• Wislicenus; Boeckler, Justus Liebigs Annalen der Chemie, 1895, vol. 285, p. 17,20
  作者：Wislicenus、Boeckler

  DOI：——

  日期：——
• Quantification of Naturally Occurring Pyrrole Acids in Melanosomes
  作者：Weslyn C. Ward、Erin C. Lamb、David Gooden、Xin Chen、David J. Burinsky、John D. Simon

  DOI：10.1111/j.1751-1097.2008.00328.x

  日期：2008.5

  AbstractThree naturally occurring pyrrole acids were found in Sepia, human black hair, and bovine choroid and iris melanosomes using high‐performance liquid chromatography and mass spectrometry—pyrrole‐2,3‐dicarboxylic acid (PDCA), pyrrole‐2,3,5‐tricarboxylic acid (PTCA) and pyrrole‐2,3,4,5‐tetracarboxylic acid (PTeCA). PDCA and PTCA are common markers quantified from oxidative degradation of eumelanins. Using standards, the amounts of naturally occurring PDCA and PTCA were determined and compared to those obtained following peroxide oxidation of the same samples. Because the naturally occurring acids are water soluble, these results indicate that care must be exercised when comparing PDCA and PTCA yields from the degradation analyses of melanins isolated and prepared by different methods. This work also establishes that PTeCA is a naturally occurring pyrrole acid in melanosomes.
• ,, ... und ehrt mir ihre Kunst!“ – Evaluierung historischer und neuer Synthesewege zu 1,5-Dihydroxy-6-oxo-1,6-dihydropyridin-2-carbonsäure und 1,3-Dihydroxy-2-oxo-3-pyrrolin-4-carbonsäure / “. . . and honour their art!” – Evaluation of Historical and New Routes to 1,5-Dihydroxy-6-oxo-1,6- dihydropyridine-2-carboxylic Acid and 1,3-Dihydroxy-2-oxo-3-pyrroline-4-carboxylic Acid
  作者：Dennis Wiedemann、Andreas Grohmann

  DOI：10.1515/znb-2009-11-1206

  日期：2009.12.1

  ,, ... und ehrt mir ihre Kunst!“ – Evaluierung historischer und neuer Synthesewege zu 1,5-Dihydroxy-6-oxo-1,6-dihydropyridin-2-carbonsäure und 1,3-Dihydroxy-2-oxo-3-pyrrolin-4-carbonsäure / “. . . and honour their art!” – Evaluation of Historical and New Routes to 1,5-Dihydroxy-6-oxo-1,6- dihydropyridine-2-carboxylic Acid and 1,3-Dihydroxy-2-oxo-3-pyrroline-4-carboxylic Acid

  „... und ehrt mir ihre Kunst!“ – 评估历史和新的合成途径到1,5-二羟基-6-酮基-1,6-二氢吡啶-2-羧酸和1,3-二羟基-2-酮基-3-吡咯烯-4-羧酸 / “. . . and honour their art!” – 评估历史和新的合成途径到1,5-二羟基-6-酮基-1,6-二氢吡啶-2-羧酸和1,3-二羟基-2-酮基-3-吡咯烯-4-羧酸