3,5-di-tert-butyl-4'-nitrobiphenyl | 279242-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-tert-butyl-4'-nitrobiphenyl
• 英文别名: 1,3-Ditert-butyl-5-(4-nitrophenyl)benzene；1,3-ditert-butyl-5-(4-nitrophenyl)benzene
• CAS: 279242-15-8
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: VMDDJXGVFNRVRF-UHFFFAOYSA-N

物化性质

• 熔点：
  97.6-98.4 °C
• 沸点：
  405.6±34.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-di-tert-butyl-4'-nitrobiphenyl 在 四(三苯基膦)钯 盐酸 、 tin 、 copper(l) iodide 、 二异丙胺 、 benzyl triethylammonium dichloroiodate 、 sodium nitrite 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.25h， 生成 2-[5-(3,5-Ditert-butylphenyl)-2-iodophenyl]ethynyl-tri(propan-2-yl)silane
  参考文献：
  名称：

  Carbon Networks Based on Dehydrobenzoannulenes. 5. Extension of Two-Dimensional Conjugation in Graphdiyne Nanoarchitectures

  摘要：

  The synthesis and optical properties of a series of multinanometer-sized substructures of the phenyl-diacetylene carbon allotrope, graphdiyne, are described. These molecules are among the largest and most complex annulenic systems yet prepared, with extension of linear conjugation in two-dimensions to over twice that of any previously reported planar macrocycle. The graphdiyne substructures are constructed through convergent syntheses, taking advantage of three key intermediates and silane-protected phenylacetylenes. Intramolecular macrocyclization of alpha,omega-polyyne precursors via Cu-niediated or Pd-catalyzed oxidative homocoupling affords five new graphdiyne "oligomers" possessing two to flour fused 1.8-membered rings. The attempted synthesis of a six-ring analogue is also reported.

  DOI：

  10.1021/jo050926v
• 作为产物：
  描述：

  3,5-二叔丁基溴苯 在 四(三苯基膦)钯 barium dihydroxide 、 叔丁基锂 作用下， 以 乙二醇二甲醚 、 乙醚 、 正戊烷 为溶剂， 反应 8.0h， 生成 3,5-di-tert-butyl-4'-nitrobiphenyl
  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.
• Carbon Networks Based on Dehydrobenzoannulenes. 5. Extension of Two-Dimensional Conjugation in Graphdiyne Nanoarchitectures
  作者：Jeremiah A. Marsden、Michael M. Haley

  DOI：10.1021/jo050926v

  日期：2005.12.1

  The synthesis and optical properties of a series of multinanometer-sized substructures of the phenyl-diacetylene carbon allotrope, graphdiyne, are described. These molecules are among the largest and most complex annulenic systems yet prepared, with extension of linear conjugation in two-dimensions to over twice that of any previously reported planar macrocycle. The graphdiyne substructures are constructed through convergent syntheses, taking advantage of three key intermediates and silane-protected phenylacetylenes. Intramolecular macrocyclization of alpha,omega-polyyne precursors via Cu-niediated or Pd-catalyzed oxidative homocoupling affords five new graphdiyne "oligomers" possessing two to flour fused 1.8-membered rings. The attempted synthesis of a six-ring analogue is also reported.