2,5-bis<(N,N-dimethylamino)methyl>-3,4-diphenylpyrrole | 172959-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-bis<(N,N-dimethylamino)methyl>-3,4-diphenylpyrrole
• 英文别名: 2,5-bis(dimethylaminomethyl)-3,4-diphenylpyrrole；1-[5-[(dimethylamino)methyl]-3,4-diphenyl-1H-pyrrol-2-yl]-N,N-dimethylmethanamine
• CAS: 172959-65-8
• 化学式: C₂₂H₂₇N₃
• 分子量: 333.476
• InChiKey: BQVNUNSDOGJRQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  22.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis<(N,N-dimethylamino)methyl>-3,4-diphenylpyrrole 在 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.17h， 生成 2,3,12,13-tetraethyl-7,8.17,18-tetraphenylporphyrin
  参考文献：
  名称：

  Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry

  摘要：

  New methodology was developed for synthesis of regiochemically pure porphyrins with D-2h symmetry (e.g. 9) via tetramerization reactions involving two different pyrroles. The two pyrrole components were a 2,5-diunsubstituted pyrrole (e.g. 11) and a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g, 10), the latter being formed from a 2,5-di-unsubstituted pyrrole by treatment with excess Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide). A bis-butanoporphyrin 16 was transformed into the corresponding opp-bis-benzoporphyrin 17 by treatment with DDQ. The synthetic method was further extended to allow the synthesis of more unsymmetrical porphyrins, with C-2v symmetry (e.g. 32), by reacting a tripyrrane (e.g. 27) with a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g. 18). The structures and substituent arrays in both type of porphyrins were confirmed by single-crystal X-ray crystallography.

  DOI：

  10.1021/jo951870f
• 作为产物：
  描述：

  3,4-二苯基-1H-吡咯 、 n,n-二甲基亚甲基碘化胺 以 硝基甲烷 为溶剂， 以83%的产率得到2,5-bis<(N,N-dimethylamino)methyl>-3,4-diphenylpyrrole
  参考文献：
  名称：

  Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry

  摘要：

  New methodology was developed for synthesis of regiochemically pure porphyrins with D-2h symmetry (e.g. 9) via tetramerization reactions involving two different pyrroles. The two pyrrole components were a 2,5-diunsubstituted pyrrole (e.g. 11) and a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g, 10), the latter being formed from a 2,5-di-unsubstituted pyrrole by treatment with excess Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide). A bis-butanoporphyrin 16 was transformed into the corresponding opp-bis-benzoporphyrin 17 by treatment with DDQ. The synthetic method was further extended to allow the synthesis of more unsymmetrical porphyrins, with C-2v symmetry (e.g. 32), by reacting a tripyrrane (e.g. 27) with a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g. 18). The structures and substituent arrays in both type of porphyrins were confirmed by single-crystal X-ray crystallography.

  DOI：

  10.1021/jo951870f

文献信息

• Synthesis and reactivity of iron–dinitrogen complexes bearing anionic methyl- and phenyl-substituted pyrrole-based PNP-type pincer ligands toward catalytic nitrogen fixation
  作者：Yoshiya Sekiguchi、Shogo Kuriyama、Aya Eizawa、Kazuya Arashiba、Kazunari Nakajima、Yoshiaki Nishibayashi

  DOI：10.1039/c7cc06987a

  日期：——

  prepared and characterized by X-ray analysis. The former complex is found to work as a more effective catalyst than that bearing a non-substituted PNP-type pincer ligand toward the transformation of nitrogen gas into ammonia and hydrazine under mild reaction conditions.

  制备了带有甲基和苯基取代的吡咯基阴离子PNP型钳形配体的铁二氮配合物，并通过X射线分析对其进行了表征。发现前一种配合物比带有未取代的PNP型夹钳配体的催化剂更有效，可在温和的反应条件下将氮气转化为氨和肼。
• Simple Methodology for Syntheses of Porphyrins Possessing Multiple Peripheral Substituents with an Element of Symmetry
  作者：Liem T. Nguyen、Mathias O. Senge、Kevin M. Smith

  DOI：10.1021/jo951870f

  日期：1996.1.1

  New methodology was developed for synthesis of regiochemically pure porphyrins with D-2h symmetry (e.g. 9) via tetramerization reactions involving two different pyrroles. The two pyrrole components were a 2,5-diunsubstituted pyrrole (e.g. 11) and a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g, 10), the latter being formed from a 2,5-di-unsubstituted pyrrole by treatment with excess Eschenmoser's reagent (N,N-dimethylmethyleneammonium iodide). A bis-butanoporphyrin 16 was transformed into the corresponding opp-bis-benzoporphyrin 17 by treatment with DDQ. The synthetic method was further extended to allow the synthesis of more unsymmetrical porphyrins, with C-2v symmetry (e.g. 32), by reacting a tripyrrane (e.g. 27) with a 2,5-bis[(N,N-dimethylamino)methyl]pyrrole (e.g. 18). The structures and substituent arrays in both type of porphyrins were confirmed by single-crystal X-ray crystallography.