2,2',4,4'-tetramethyl-3,3'-dipyrromethane | 444753-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,2',4,4'-tetramethyl-3,3'-dipyrromethane
• 英文别名: bis(2,4-dimethylpyrrole-3-yl)methane；2,2',4,4'-tetramethyl-3,3'-dipyrrolylmethane；3,3'-methanediylbis(2,4-dimethyl-1H-pyrrole)；bis(2,4-dimethyl-1H-pyrrol-3-yl)methane；2,2',4,4'-tetramethyldipyrrolylmethane-3,3'；bis-(2,4-dimethyl-pyrrol-3-yl)-methane；Bis-(2,4-dimethyl-pyrrol-3-yl)-methan；3-[(2,4-dimethyl-1H-pyrrol-3-yl)methyl]-2,4-dimethyl-1H-pyrrole
• CAS: 444753-85-9
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: VHGUCFUWRMXWHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,4-二甲基-1H-吡咯-2-羧醛 、 2,2',4,4'-tetramethyl-3,3'-dipyrromethane 在 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以84.4%的产率得到bis(2,3,7,9-tetramethyldipyrrolylmethen-8-yl)methane dihydrobromide
  参考文献：
  名称：

  Synthesis and spectral analysis of alkyl-substituted 3,3′-bis(dipyrrolylmethenes)

  摘要：

  Four new alkyl-substituted 3,3'-bis(dipyrrolylmethene) dihydrobromides containing from 4 to 10 alkyl substituents were synthesized. In a highly alkylated ligand of these substances one of the hydrogen atoms of the 3,3'-methylene spacer was substituted with a phenyl group. The compounds obtained were studied by IR, H-1 NMR, electron absorption, and fluorescent spectroscopy. The increased alkylation degree of pyrroles and the introduction of an aryl substituent in the 3,3'-spacer causes a significant high-frequency shift of the N-H stretching vibrations in the IR spectra, an upfield shift of the NH-proton signals in H-1 NMR spectra, a decrease in the auxochromic effects of protons on the aromatic system of chromophore in the composition of salts. The red shift of maximum of the strong band in electron absorption spectra and the emission spectra of compounds in DMF, DMSO, C5H5N, C6H6, and CHCl3 was established. The salts obtained are stable in benzene and chloroform, while in electron-donor solvents the irreversible processes of solvolytic dissociation of salts to free organic base and HBr take place.

  DOI：

  10.1134/s1070363209110243
• 作为产物：
  描述：

  2,2',4,4'-tetramethyl-5,5'-bis(ethoxycarbonyl)dipyrrolylmethane-3,3' 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 1.0h， 以0.51 g的产率得到2,2',4,4'-tetramethyl-3,3'-dipyrromethane
  参考文献：
  名称：

  Synthesis and spectral properties of helicate of cobalt(II) with Bis(1,2,3,7,9-pentamethyldipyrrolylmethen-3-yl)methane

  摘要：

  DOI：

  10.1134/s1070363211010324

文献信息

• Fischer,H.; Bartholomaeus, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1913, vol. 83, p. 58
  作者：Fischer,H.、Bartholomaeus

  DOI：——

  日期：——
• New fluorescent chemosensor for Zn2+ ions on the basis of 3,3′-bis(dipyrrolylmethene)
  作者：N. A. Dudina、E. V. Antina、G. B. Guseva、A. I. V’yugin、A. S. Semeikin

  DOI：10.1134/s107042801312004x

  日期：2013.12

  Luminescence study of the reaction of 3,3'-methanediylbis(2,4,7,8,9-pentamethyldipyrrolylmethene) (H2L) with a number of metal salts showed that this compound is an efficient fluorescent chemosensor for Zn2+ ions in organic solvents. The selectivity and sensitivity of H2L were estimated in various solvents in the presence of other metal cations (Na+, Mg2+, Co2+, Ni2+, Cu2+, Cd2+, Hg2+, Pb2+).
• 3,3′-bis(dipyrrolylmethenes) as new chelating ligands: Synthesis and spectral properties
  作者：G. B. Guseva、N. A. Dudina、E. V. Antina、A. I. V’yugin、A. S. Semeikin

  DOI：10.1134/s1070363208060200

  日期：2008.6

  Hydrobromides of' thre-- new alkyl-substituted tetrapyrrole ligands with an open chain, in which the dipyrrolylmethenc 1ragments are linked by a CH-spacer at the 3,3'-pyrrole carbon atoms, were synthesized and studied by IR, 1H NMR, and el( ctronic absorption spectroscopy. As compared to the 2,2' isorners (alkyl derivatives of' biladiene-a,c) and inonorners (2,2'-, 2,3'-, and 3,Y-dipyrrolylinethenes, the ef't'ect of' structural t'actors is mandested in a considerable (up to 19-3 1 nm) bathochromic shi 11 ol'the strong band in the electronic spectrum, an increase in the N-H stretching vibration 1requency in the IR spectra (by more than 30 crn'). and a decrease in the stability of' 3,3'-bis(dipyrrolylinethene) salts. The solvent effect is manit'ested in small changes in the quantitative characteristics of the electronic absorption spectra o4' 3,3'-tetrapyrrole hydrobromidcs in C,H,, CC14, CHCl,. CHC13, anJ alcohols. In DMF, DMSO, and C5H5N, the salts undergo solvolytic dissociation to the 1ree ligands and HBr, which accelerates in dilute solutions (<10 -4 M) and with an increase in the electron-donor power of' the solvent. The auxochrornic effects of' protons in the electronic absorption spectra ol'the salts, compared to ligands, were estimated quantitatively.
• Tetra-N-confused Cyclohexapyrrole:  The Unusual Product Formed by Condensation of 3,3‘-Dipyrromethane with Tripyrrin-aldehyde
  作者：Yi Zhang、Qingqi Chen、Zheming Wang、Chunhua Yan、Genpei Li、Jin Shi Ma

  DOI：10.1021/jo0163748

  日期：2002.7.1

  Novel tetra-N-confused cyclohexapyrrole is synthesized for the first time via condensation of tripyrrinonealdehyde with bis(2,4-dimethylpyrrole-3-yl)methane in the presence of p-toluenesulfonic acid monohydrate. X-ray crystal analysis indicates that it adopts a nonplanar conformation with a conelike shape.
• Synthesis and spectral analysis of alkyl-substituted 3,3′-bis(dipyrrolylmethenes)
  作者：E. V. Antina、G. B. Guseva、N. A. Dudina、A. I. V’yugin、A. S. Semeikin

  DOI：10.1134/s1070363209110243

  日期：2009.11

  Four new alkyl-substituted 3,3'-bis(dipyrrolylmethene) dihydrobromides containing from 4 to 10 alkyl substituents were synthesized. In a highly alkylated ligand of these substances one of the hydrogen atoms of the 3,3'-methylene spacer was substituted with a phenyl group. The compounds obtained were studied by IR, H-1 NMR, electron absorption, and fluorescent spectroscopy. The increased alkylation degree of pyrroles and the introduction of an aryl substituent in the 3,3'-spacer causes a significant high-frequency shift of the N-H stretching vibrations in the IR spectra, an upfield shift of the NH-proton signals in H-1 NMR spectra, a decrease in the auxochromic effects of protons on the aromatic system of chromophore in the composition of salts. The red shift of maximum of the strong band in electron absorption spectra and the emission spectra of compounds in DMF, DMSO, C5H5N, C6H6, and CHCl3 was established. The salts obtained are stable in benzene and chloroform, while in electron-donor solvents the irreversible processes of solvolytic dissociation of salts to free organic base and HBr take place.