2-(4-tertButylphenyl)-5-nitropyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-tertButylphenyl)-5-nitropyridine
• 英文别名: 4tBu-2PhNp；2-(4-Tert-butylphenyl)-5-nitropyridine；2-(4-tert-butylphenyl)-5-nitropyridine
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: JNZMDUPCHZSSCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-5-硝基吡啶 、 4-叔丁基溴苯 在 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 叔丁基锂 、 zinc(II) chloride 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 生成 2-(4-tertButylphenyl)-5-nitropyridine
  参考文献：
  名称：

  From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of nitroaromatics in Salmonella typhimurium

  摘要：

  Derivatives of 4-nitrobiphenyl, 4-nitrosobiphenyl, 2-phenyl-5-nitropyridine (2-aza-4-nitrobiphenyl) and 2-nitrofluorene, bearing various alkyl substituents far away from the nitro group (4'-position in nitrobiphenyls, 7-position in 2-nitrofluorenes) were synthesised and tested for mutagenic potency in strains TA98 and TA100 of Salmonella typhimurium. In the absence of S9 in both strains, mutagenicity of all compounds decreased with increasing steric demand of the attached alkyl groups as, e.g., for the 4-nitrobiphenyl series in the order 4'-H > 4'-Me > 4'-Et > 4'-nBu > 4'-iPr > di-tBu > 4'-Ad (Ad = adamantyl). Changes of the molecular shape from 'planar' to non-planar caused by the bulk of the introduced substituents (without influencing the twisting of the nitro substituent or the phenyl rings in the biphenyl compounds) may be responsible for this effect by interfering with an efficient intercalation into DNA.A comparison between experimental and theoretical values as calculated from recently developed equations (QSAR) confirmed our previous results (see the preceding paper) that mutagenicity of alkyl-substituted nitroaromatics cannot be predicted by hydrophobicity and LUMO-energies alone without including steric parameters. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(00)00013-9

文献信息

• From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of nitroaromatics in Salmonella typhimurium
  作者：Markus Klein、Lothar Erdinger、Gernot Boche

  DOI：10.1016/s1383-5718(00)00013-9

  日期：2000.4

  Derivatives of 4-nitrobiphenyl, 4-nitrosobiphenyl, 2-phenyl-5-nitropyridine (2-aza-4-nitrobiphenyl) and 2-nitrofluorene, bearing various alkyl substituents far away from the nitro group (4'-position in nitrobiphenyls, 7-position in 2-nitrofluorenes) were synthesised and tested for mutagenic potency in strains TA98 and TA100 of Salmonella typhimurium. In the absence of S9 in both strains, mutagenicity of all compounds decreased with increasing steric demand of the attached alkyl groups as, e.g., for the 4-nitrobiphenyl series in the order 4'-H > 4'-Me > 4'-Et > 4'-nBu > 4'-iPr > di-tBu > 4'-Ad (Ad = adamantyl). Changes of the molecular shape from 'planar' to non-planar caused by the bulk of the introduced substituents (without influencing the twisting of the nitro substituent or the phenyl rings in the biphenyl compounds) may be responsible for this effect by interfering with an efficient intercalation into DNA.A comparison between experimental and theoretical values as calculated from recently developed equations (QSAR) confirmed our previous results (see the preceding paper) that mutagenicity of alkyl-substituted nitroaromatics cannot be predicted by hydrophobicity and LUMO-energies alone without including steric parameters. (C) 2000 Elsevier Science B.V. All rights reserved.