tetraethyl 1H-pyrrole-2,3,4,5-tetracarboxylate | 951157-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tetraethyl 1H-pyrrole-2,3,4,5-tetracarboxylate
• 英文别名: tetraethyl 2,3,4,5-pyrroletetracarboxylate
• CAS: 951157-13-4
• 化学式: C₁₆H₂₁NO₈
• 分子量: 355.345
• InChiKey: KSKKEWSIIPHVTB-UHFFFAOYSA-N

物化性质

• 沸点：
  465.3±40.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetraethyl 1H-pyrrole-2,3,4,5-tetracarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以68%的产率得到pyrrole-2,3,4,5-tetracarboxylic acid
  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：

  丁炔二酸二乙酯 在 正丙胺 、 四丁基溴化铵 、 铁粉 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以40%的产率得到tetraethyl 1H-pyrrole-2,3,4,5-tetracarboxylate
  参考文献：
  名称：

  通过电生成的碱和Fe 3+离子的催化，有效地从缺电子炔烃中合成对称的氧杂环和氮杂环

  摘要：

  已开发出一种有效的方法，可通过电化学诱导的两步法从缺电子的炔烃和醇或胺合成氧和氮杂环。第一步涉及电生成碱（EGB）催化加氢醇化或加氢胺化过程。第二步，电生成的Fe 3+离子和强碱可以协同催化环化过程，得到对称的杂环。研究了一些关键因素并讨论了反应机理。

  DOI：

  10.1016/j.tet.2011.04.058

文献信息

• [3+2] Cycloaddition of Diazocarbonyl Compounds to 1,1-Dinitroethenes: Synthesis of Functionalized <i>gem</i>-Dinitrocyclopropanes
  作者：Tamara Kuznetsova、Olga Ivanova、Ekaterina Budynina、Elena Averina、Yurii Grishin、Nikolai Zefirov

  DOI：10.1055/s-2007-983727

  日期：2007.7

  The synthesis of functionalized GEM-dinitrocyclopropanes via [3+2] cycloaddition of diazocarbonyl compounds with 1,1-dinitroethenes [in some cases in the presence of Mo(CO) 6 as catalyst] has been developed.

  通过重氮羰基化合物与 1,1-二硝基乙烯的 [3+2] 环加成 [在某些情况下，在 Mo(CO) 6 作为催化剂的存在下] 合成功能化 GEM-二硝基环丙烷已得到开发。
• 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.
• Effective synthesis of symmetrical oxygen- and nitrogen-heterocycles from electron-deficient alkynes via the catalysis of electrogenerated base and Fe3+ ions
  作者：Chuan-Hua Li、Gao-Qing Yuan、Jun-Hua Zheng、Zai-Jun He、Chao-Rong Qi、Huan-Feng Jiang

  DOI：10.1016/j.tet.2011.04.058

  日期：2011.6

  An efficient method has been developed for the synthesis of oxygen- and nitrogen-heterocycles from electron-deficient alkynes and alcohol or amines via electrochemically induced two-step process. The first step involves that the electrogenerated base (EGB) catalyzes hydroalcoholization or hydroamination process. In the second step, Fe3+ ions and strong bases electrogenerated can synergically catalyze

  已开发出一种有效的方法，可通过电化学诱导的两步法从缺电子的炔烃和醇或胺合成氧和氮杂环。第一步涉及电生成碱（EGB）催化加氢醇化或加氢胺化过程。第二步，电生成的Fe 3+离子和强碱可以协同催化环化过程，得到对称的杂环。研究了一些关键因素并讨论了反应机理。