3,5,3',5'-tetramethyl-4,4'-phenylmethanediyl-bis-pyrrole-2-carboxylic acid diethyl ester | 95943-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,5,3',5'-tetramethyl-4,4'-phenylmethanediyl-bis-pyrrole-2-carboxylic acid diethyl ester
• 英文别名: Bis-(5-ethoxycarbonyl-2,4-dimethyl-pyrrol-3-yl)-phenyl-methan；3,5,3',5'-tetramethyl-4,4'-benzylidene-bis-pyrrole-2-carboxylic acid diethyl ester；3,5,3',5'-Tetramethyl-4,4'-benzyliden-bis-pyrrol-2-carbonsaeure-diaethylester
• CAS: 95943-48-9
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: YDRCWDYSKGOCMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5,3',5'-tetramethyl-4,4'-phenylmethanediyl-bis-pyrrole-2-carboxylic acid diethyl ester 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 以99%的产率得到3,3'-(phenylmethylene)bis(2,4-dimethyl-1H-pyrrole)
  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：

  3,5-二甲基-1H-吡咯-2-甲酸乙酯 、 苯甲醛 在 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以95%的产率得到3,5,3',5'-tetramethyl-4,4'-phenylmethanediyl-bis-pyrrole-2-carboxylic acid diethyl ester
  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

文献信息

• Treibs; Fritz, Justus Liebigs Annalen der Chemie, 1958, vol. 611, p. 162,188
  作者：Treibs、Fritz

  DOI：——

  日期：——