4-methoxy-2',6'-dinitrobiphenyl | 5110-82-7

• 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: 4-methoxy-2',6'-dinitrobiphenyl
• 英文别名: 2,6-Dinitro-4'-methoxy-biphenyl；2-(4-Methoxyphenyl)-1,3-dinitrobenzene
• CAS: 5110-82-7
• 化学式: C₁₃H₁₀N₂O₅
• 分子量: 274.233
• InChiKey: DKRAHZQSRVQXCS-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  402.1±35.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-2',6'-dinitrobiphenyl 在 吡啶 、 2,3,5-三甲基吡啶 、 六甲基磷酰三胺 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四溴化碳 、 双氧水 、 sodium 、 三氯化硼 、 三溴化硼 、 铁粉 、 sodium hydride 、 potassium carbonate 、 氯化铵 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 215.7h， 生成 3,5-bis<3-(2-formyl-3,5-dimethylphenoxy)propyl>-4-hydroxy-2',6'-bis<6-(2-formyl-3,5-dimethylphenoxy)hexanamido>biphenyl
  参考文献：
  名称：

  Pendant-capped porphyrins. 1. The synthesis of a biphenyl pendant-capped iron(III) porphyrin model of catalase

  摘要：

  A phenol pendant-capped porphyrin ((PHPCP)H2) and its iron(III) complex ((PPCP)Fe(III)) have been synthesized. H-1 and C-13 NMR were used to characterize all intermediates leading to the final product. In addition, the heteronuclear C-13-H-1 shift correlation experiment was used to further characterize the tetraaldehyde precursor of the pendant-capped porphyrin. Proton and carbon chemical shifts for the free base porphyrin (PHPCP)H2 were assigned by using one-dimensional NMR experiments (including C-13 APT) and two-dimensional homonuclear COSY and ROESY experiments. In (PHPCP)H2, the phenol that provides the ligand is hung from the ceiling of a vaulted dome or tepee with protected walls supported by four legs that are anchored to the 2-position of the phenyl rings at the 5,10,15,20-meso-carbons of (TPP)H2. In the ground-state structure of (PPCP)Fe(III), the phenol is dissociated such that the resultant phenolate species is ligated to the high-spin (S = 5/2) iron(III). Ligation of phenolate and iron moieties is established by (i) comparison of H-1 NMR to the H-1 NMR of the phenolate complex of [(TPP)Fe(III)]+; (ii) comparison of the UV/vis spectrum to that for the phenolate complex of [(TPP)Fe(III)]+; (iii) disappearance of the O-H stretch in the IR accompanying complexation of (PHPCP)H2 with Fe(III); and (iv) laser desorption mass spectroscopy. At the active site of catalase, the protoporphyrin-IX iron(III) is ligated to the phenolate form of a tyrosine residue.

  DOI：

  10.1021/ja00021a042
• 作为产物：
  描述：

  1,3-二硝基苯 、 4-碘苯甲醚 生成 4-methoxy-2',6'-dinitrobiphenyl
  参考文献：
  名称：

  使用叔丁醇铜（I）的不对称联苯合成

  摘要：

  通过叔丁醇铜（I）和吡啶将1，3-二硝基苯与碘代芳基偶合，为制备2，6-二硝基联苯提供了便利的途径。

  DOI：

  10.1039/c39790000294

文献信息

• Total Synthesis of Dictyodendrins B and E, and Formal Synthesis of Dictyodendrin C
  作者：Pengyu Tao、Jingjing Liang、Yanxing Jia

  DOI：10.1002/ejoc.201402672

  日期：2014.9

  A full account of the concise total syntheses of dictyodendrins B and E, and the formal synthesis of dictyodendrin C are described. A palladium-catalysed Larock indole synthesis was used to form the highly substituted indole core, and a palladium-mediated one-pot consecutive Buchwald–Hartwig amination/C–H activation reaction was used to construct the key pyrrolo[2,3-c]carbazole core. Unsuccessful synthetic

  描述了 dictyodendrin B 和 E 的简明全合成以及 dictyodendrin C 的正式合成。钯催化的 Larock 吲哚合成用于形成高度取代的吲哚核心，钯介导的一锅连续 Buchwald-Hartwig 胺化/C-H 活化反应用于构建关键的吡咯[2,3-c]咔唑核。还讨论了不成功的合成策略。
• Carter, Stephen D.; Wallace, Timothy W., Journal of Chemical Research, Miniprint, 1985, # 5, p. 1601 - 1633
  作者：Carter, Stephen D.、Wallace, Timothy W.

  DOI：——

  日期：——
• 118. The Ullmann biaryl synthesis. Part II. The effect of m-dinitrated diluents on the self-condensation of iodobenzene
  作者：James Forrest

  DOI：10.1039/jr9600000574

  日期：——
• Cornforth, John; Sierakowski, Andrew F.; Wallace Timothy W., Journal of the Chemical Society. Perkin transactions I, 1982, # 10, p. 2299 - 2316
  作者：Cornforth, John、Sierakowski, Andrew F.、Wallace Timothy W.

  DOI：——

  日期：——
• First synthesis of a pendant-capped porphyrin. A biphenyl pendant-capped porphyrin model of catalase
  作者：Chang Hee Lee、Barbara Garcia、Thomas C. Bruice

  DOI：10.1021/ja00173a062

  日期：1990.8