1H-吡咯-2,3,5-三甲醛 | 81697-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1H-吡咯-2,3,5-三甲醛
• 英文名称: 1H-pyrrole-2,3,5-tricarbaldehyde
• 英文别名: pyrrole-2,3,5-tricarboxaldehyde；pyrrole-2,3,5-tricarbaldehyde
• CAS: 81697-99-6
• 化学式: C₇H₅NO₃
• 分子量: 151.122
• InChiKey: VUXRQLMUKQMWRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡咯-3-甲醛 在 tetrafluoroboric acid 、 溶剂黄146 、 mercury(II) oxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1H-吡咯-2,3,5-三甲醛
  参考文献：
  名称：

  A convenient general method for the synthesis of pyrrole-2,5-dicarbaldehydes

  摘要：

  A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35% aq. HBF4-DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65%, whilst that of the derivatives was 32-90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield.

  DOI：

  10.1039/p19930002939

文献信息

• Pyrrole chemistry. XXIV. The Vilsmeier formylation and the cyanation of pyrrole acetals. A synthesis of pyrrole-2,3,5-tricarboxaldehyde
  作者：Charles E. Loader、Graham H. Barnett、Hugh J. Anderson

  DOI：10.1139/v82-060

  日期：1982.2.15

  The preparation of the acetals of a number of pyrrole mono- and dicarboxaldehydes is described. It is shown that, provided the reactivity of the unsubstituted ring positions on the pyrrole nucleus is not too low, a carboxyaldehyde or a carbonitrile group may be substituted onto the pyrrole ring using the Vilsmeier reaction or chlorosulfonyl isocyanate respectively. Vilsmeier formylation of the diacetal, 2,4-di(5,5-dimethyl- 1,3-dioxan-2-yl)-pyrrole, followed by hydrolysis gave pyrrole-2,3,5-tricarboxaldehyde.

  描述了一系列吡咯单酸和二酸的缩醛制备方法。结果表明，只要吡咯核上未取代的位置的反应性不太低，可以使用Vilsmeier反应或氯磺酰异氰酸酯将羧醛或碳氰基取代到吡咯环上。对二缩醛2,4-二(5,5-二甲基-1,3-二氧杂环戊烷-2-基)-吡咯进行Vilsmeier甲酰化反应，然后水解得到吡咯-2,3,5-三酸醛。
• Synthesis, antiviral, cytotoxicity and antitumor evaluations of A₄ type of porphyrin derivatives
  作者：Ahmed A. Fadda、Rasha E. El-Mekawy、Ahmed I. El-Shafei

  DOI：10.1142/s1088424615500480

  日期：2015.6

  This manuscript describes the synthesis of a new series of porphyrin structures 4a–4m, 7, 9, 12 and 14. These structures were investigated against two types of viruses such as HIV-1 and HSV-1. Also they were screened for their antitumor activity. Among all tested compounds, it was found that compound 4b showed a high activity against HIV-1 and HSV-1 and against four different tumor cell lines. Most of the tested compounds showed a moderate degree of a potent antimicrobial activity. The structure of these compounds was confirmed on the basis of their analytical and spectral data such as UV-vis, IR, ¹³ C NMR, ¹ H NMR spectroscopy and mass spectral data.

  本手稿描述了一系列新的卟啉结构 4a-4m、7、9、12 和 14 的合成。这些结构针对 HIV-1 和 HSV-1 两种病毒进行了研究。此外，还对它们的抗肿瘤活性进行了筛选。结果发现，在所有测试化合物中，化合物 4b 对 HIV-1 和 HSV-1 以及四种不同的肿瘤细胞株具有较高的活性。大多数测试化合物都显示出中等程度的强效抗菌活性。根据这些化合物的分析和光谱数据，如紫外-可见光、红外光谱、13 C NMR、1 H NMR 光谱和质谱数据，确认了这些化合物的结构。
• Convenient route for the synthesis of 3-substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes
  作者：Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Laura Piscopo

  DOI：10.1039/p19960002365

  日期：——

  3-Substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes have been obtained by hydrolysis with HgO–35% aq. HBF4–DMSO of the intermediates 4 and 5 prepared by electrophilic substitution reactions on 2,5-bis(1,3-benzodithiol-2-yl)pyrrole. The overall yields starting from pyrrole ranged from 41–88%.

  通过用 HgO–35% 水溶液水解得到 3-取代和 3,4-二取代吡咯-2,5-二甲醛。通过 2,5-双(1,3-苯并二硫醇-2-基)吡咯的亲电取代反应制备中间体 4 和 5 的 HBF4-DMSO。从吡咯开始的总产率为 41-88%。
• LOADER, C. E.;BARNETT, G. H.;ANDERSON, H. J., CAN. J. CHEM., 1982, 60, N 4, 383-389
  作者：LOADER, C. E.、BARNETT, G. H.、ANDERSON, H. J.

  DOI：——

  日期：——
• A convenient general method for the synthesis of pyrrole-2,5-dicarbaldehydes
  作者：Silvano Cadamuro、Iacopo Degani、Rita Fochi、Antonella Gatti、Laura Piscopo

  DOI：10.1039/p19930002939

  日期：——

  A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported. It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35% aq. HBF4-DMSO. Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65%, whilst that of the derivatives was 32-90%. Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90% overall yield.