3,5-dinitro-4-(4-trifluoromethylphenoxy)toluene

• 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-dinitro-4-(4-trifluoromethylphenoxy)toluene
• 英文别名: 5-Methyl-1,3-dinitro-2-[4-(trifluoromethyl)phenoxy]benzene；5-methyl-1,3-dinitro-2-[4-(trifluoromethyl)phenoxy]benzene
• 化学式: C₁₄H₉F₃N₂O₅
• 分子量: 342.231
• InChiKey: UEDNUYLDQRERHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-dinitro-4-(4-trifluoromethylphenoxy)toluene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以83%的产率得到3,5-diamino-4-(4-trifluoromethylphenoxy)toluene
  参考文献：
  名称：

  3,5-Dinitro-4-(4-trifluoromethylphenoxy)toluene, Conformationally Related to Thyroid Hormones

  摘要：

  The title compound, C14H9F3N2O5, was synthesized as a crystalline intermediate in the synthetic route to the diiodo compound which is a potential thyroid-hormone analog. Although all the bond distances and angles have normal values in the crystal structure, there was non-coplanarity of the nitro groups [dihedral angles between the phenyl group and N(1), O(1), O(2) and N(2), O(3), O(4) are 21.5 and 60.3 degrees, respectively] and significant asymmetry in the bond angles at the pivotal atom, C(4), of the dinitrophenyl ring. The interplanar angle between the phenyl rings is 80.2 degrees. Energy-refined structures for the dinitro and diiodo compounds gave interplanar angles of 80.05 and 79.65 degrees, respectively. The skewed or twist-skewed conformation seen in thyroid hormones is reasonably well preserved in these model systems.

  DOI：

  10.1107/s0108270194005305
• 作为产物：
  描述：

  对三氟甲基苯酚 、 2,6-二硝基-4-甲基苯酚 在 吡啶 、 甲基磺酰氯 作用下， 反应 0.5h， 以68%的产率得到3,5-dinitro-4-(4-trifluoromethylphenoxy)toluene
  参考文献：
  名称：

  3,5-Dinitro-4-(4-trifluoromethylphenoxy)toluene, Conformationally Related to Thyroid Hormones

  摘要：

  The title compound, C14H9F3N2O5, was synthesized as a crystalline intermediate in the synthetic route to the diiodo compound which is a potential thyroid-hormone analog. Although all the bond distances and angles have normal values in the crystal structure, there was non-coplanarity of the nitro groups [dihedral angles between the phenyl group and N(1), O(1), O(2) and N(2), O(3), O(4) are 21.5 and 60.3 degrees, respectively] and significant asymmetry in the bond angles at the pivotal atom, C(4), of the dinitrophenyl ring. The interplanar angle between the phenyl rings is 80.2 degrees. Energy-refined structures for the dinitro and diiodo compounds gave interplanar angles of 80.05 and 79.65 degrees, respectively. The skewed or twist-skewed conformation seen in thyroid hormones is reasonably well preserved in these model systems.

  DOI：

  10.1107/s0108270194005305

文献信息

• 3,5-Dinitro-4-(4-trifluoromethylphenoxy)toluene, Conformationally Related to Thyroid Hormones
  作者：J. D. McKinney、S. C. Agarwal、W. T. Padgett、G. R. Lambert、P. Singh、S. Nesnow

  DOI：10.1107/s0108270194005305

  日期：1995.3.15

  The title compound, C14H9F3N2O5, was synthesized as a crystalline intermediate in the synthetic route to the diiodo compound which is a potential thyroid-hormone analog. Although all the bond distances and angles have normal values in the crystal structure, there was non-coplanarity of the nitro groups [dihedral angles between the phenyl group and N(1), O(1), O(2) and N(2), O(3), O(4) are 21.5 and 60.3 degrees, respectively] and significant asymmetry in the bond angles at the pivotal atom, C(4), of the dinitrophenyl ring. The interplanar angle between the phenyl rings is 80.2 degrees. Energy-refined structures for the dinitro and diiodo compounds gave interplanar angles of 80.05 and 79.65 degrees, respectively. The skewed or twist-skewed conformation seen in thyroid hormones is reasonably well preserved in these model systems.