4-丁基-3,5-二甲基-1H-吡咯-2-甲醛 | 220845-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-丁基-3,5-二甲基-1H-吡咯-2-甲醛
• 中文别名: 亚甲基二(6-苯甲酰苯-1,2,3,4-四基)八(6-重氮基-5,6-二氢-5-羰基萘-1-磺化)
• 英文名称: 2-formyl-3,5-dimethyl-4-butylpyrrole
• 英文别名: 4-butyl-3,5-dimethylpyrrole-2-carbaldehyde；4-Butyl-3,5-dimethyl-pyrrol-2-carbaldehyd；4-Butyl-3,5-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 220845-12-5
• 化学式: C₁₁H₁₇NO
• mdl: MFCD18810193
• 分子量: 179.262
• InChiKey: ITVUCLRIVHDQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-丁基-3,5-二甲基-1H-吡咯-2-甲醛 在 silver(I) iodate 、 zinc diacetate 、 氢溴酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 13,17-dibutyl-12,8-dimethyldinaphtho[2,1-b:1,2-g]porphyrin
  参考文献：
  名称：

  异构角度退火Dinaphthoporphyrin系统的合成：相对定位的检查和环融合的方向是影响卟啉生色因素†

  摘要：

  由两个萘并[1,2- c ]吡咯亚基和两个β-取代的吡咯构成的卟啉可产生五个异构的萘并卟啉体系。为了深入了解环融合对扩展卟啉发色团的影响，所有这五个系统均以异构体纯净形式合成。在这些合成中的四个中，使用二氢萘吡咯引入一个或两个萘亚基，然后在回流的甲苯中用DDQ脱氢，随后生成完全共轭的系统。萘吡咯还通过在磷腈碱存在下使异氰基乙酸酯与1-硝基萘反应来制备。这些化合物被证明不如其二氢萘吡咯类似物稳定，但仍可用于这些合成研究中。三异构ADJ使用麦当劳“ 2 + 2”缩合反应或通过氯化铜（II）或AgIO 3 -Zn（OAc）2的α，c-胆二烯中间体环化制备-二萘甲卟啉体系。与朝向彼此指向2个萘单元A dinaphthoporphyrin只能低收率由于稳定性和位阻因素的组合来获得，但其他两个ADJ -difused系统，可在良好的整体产率分离。但是，最终的脱氢步骤以中等收率（50-60％）发生，并且

  DOI：

  10.1021/jo040269r
• 作为产物：
  描述：

  4-丁基-3,5-二甲基-1H-吡咯-2-羧酸乙酯 在 氢氧化钾 、 三氯氧磷 作用下， 以 乙二醇 为溶剂， 反应 3.0h， 生成 4-丁基-3,5-二甲基-1H-吡咯-2-甲醛
  参考文献：
  名称：

  Berezin; Semeikin; Antina, Russian Journal of General Chemistry, 1999, vol. 69, # 12, p. 1949 - 1955

  摘要：

  DOI：

文献信息

• ——
  作者：A. S. Semeikin、M. B. Berezin、O. M. Chernova、E. V. Antina、S. A. Syrbu、T. V. Lyubimova、A. M. Kutepov

  DOI：10.1023/a:1026064923515

  日期：——

  New data on the spectral properties and solution enthalpies of unsymmetrically substituted 2-(alkyl-2-pyrrolylmethylidene) methylpyrrolium bromides (or alpha,alpha-dipyrrylmethene hydrobromides), their alpha,beta-, beta,beta-isomers, as well as their oxa and thia analogs, that is, 2-(2-furylmethylidene)- and 2-(2-thienylmethylidene)-3,4,5-trimethyl-1H-pyrrolium bromides, in solutions of organic solvents of different nature are presented. A decrease in the number of substituents, as well as replacement of the heteroatom (N) in one five-membered ring of the dipyrrylmetnehe by oxygen or sulfur atoms cause a monotonic hypsochromic shift of absorption bands in the electronic absorption spectrum and weakening of the chromophore properties of the compounds. The chromophore properties of isomers are weakened from the alpha,alpha- to alpha,beta- and beta,beta-dipyrrylmethenes. Main trends in the influence of structural factors on the specific features of thermooxidative destruction of the above-mentioned compounds were analyzed.
• Normal and Abnormal Heme Biosynthesis. 1. Synthesis and Metabolism of Di- and Monocarboxylic Porphyrinogens Related to Coproporphyrinogen-III and Harderoporphyrinogen:  A Model for the Active Site of Coproporphyrinogen Oxidase
  作者：Timothy D. Lash、Ukti N. Mani、Martin A. Drinan、Chun Zhen、Troii Hall、Marjorie A. Jones

  DOI：10.1021/jo981473f

  日期：1999.1.1

  Coproporphyrinogen oxidase (copro'gen oxidase), which catalyses the conversion of coproporphyrinogen-III via a monovinylic intermediate to protoporphyrinogen-IX, is one of the least well understood enzymes in the heme biosynthetic pathway. To develop a model for the substrate recognition and binding recognition for this enzyme, a series of substrate analogues were prepared with two alkyl substituents on positions 13 and 17 in place of the usual propionate residues. Although the required substrate probes are porphyrinogens (hexahydroporphyrins), the corresponding porphyrin methyl esters were initialy synthesized via a,c-biladiene intermediates. These were hydrolyzed and reduced with 3% sodium amalgam to give the unstable porphyrinogens needed for the biochemical investigations. These modified structures were metabolized by avian preparations of copro'gen oxidase to give monovinylic products, but the second propionate residue was not further metabolized. In three cases, the metabolites were isolated and further characterized by proton NMR spectroscopy and mass spectrometry. When methyl or ethyl groups were placed at the 13 and 17 positions, the resulting porphyrinogens were very good substrates (although the ethyl version, mesoporphyrinogen-VI, gave slightly better results), but when propyl units were introduced metabolism was significantly inhibited and the butyl-substituted structure was only slightly transformed after long incubation periods. These results suggest the presence of an active-site lipophobic region near the catalytic site for copro'gen oxidase. The observation that the related 3-vinyl- and 3-ethylporphyrinogens with 13,17-diethyl substituents were not substrates for this enzyme confirmed the need for a second propionate residue to hold the substrate in place at the catalytic site.
• Fischer; Bertl, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1934, vol. 229, p. 37,49
  作者：Fischer、Bertl

  DOI：——

  日期：——
• Berezin; Semeikin; Antina, Russian Journal of General Chemistry, 1999, vol. 69, # 12, p. 1949 - 1955
  作者：Berezin、Semeikin、Antina、Pashanova、Lehedeva、Bukushina

  DOI：——

  日期：——
• Synthesis of Isomeric Angularly Annealed Dinaphthoporphyrin Systems:  Examination of the Relative Positioning and Orientation of Ring Fusion as Factors Influencing the Porphyrin Chromophore
  作者：Jerad M. Manley、Tracy J. Roper、Timothy D. Lash

  DOI：10.1021/jo040269r

  日期：2005.2.1

  Porphyrins built up from two naphtho[1,2-c]pyrrole subunits and two β-substituted pyrroles can produce five isomeric dinaphthoporphyrin systems. To gain insights into the effects of ring fusion on extended porphyrin chromophores, all five of these systems were synthesized in isomerically pure form. In four of these syntheses, dihydronaphthopyrroles were used to introduce one or both of the naphthalene

  由两个萘并[1,2- c ]吡咯亚基和两个β-取代的吡咯构成的卟啉可产生五个异构的萘并卟啉体系。为了深入了解环融合对扩展卟啉发色团的影响，所有这五个系统均以异构体纯净形式合成。在这些合成中的四个中，使用二氢萘吡咯引入一个或两个萘亚基，然后在回流的甲苯中用DDQ脱氢，随后生成完全共轭的系统。萘吡咯还通过在磷腈碱存在下使异氰基乙酸酯与1-硝基萘反应来制备。这些化合物被证明不如其二氢萘吡咯类似物稳定，但仍可用于这些合成研究中。三异构ADJ使用麦当劳“ 2 + 2”缩合反应或通过氯化铜（II）或AgIO 3 -Zn（OAc）2的α，c-胆二烯中间体环化制备-二萘甲卟啉体系。与朝向彼此指向2个萘单元A dinaphthoporphyrin只能低收率由于稳定性和位阻因素的组合来获得，但其他两个ADJ -difused系统，可在良好的整体产率分离。但是，最终的脱氢步骤以中等收率（50-60％）发生，并且