2,2'-dinitro-6,6'-bis(propylthio)biphenyl | 302946-72-1

• 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: 2,2'-dinitro-6,6'-bis(propylthio)biphenyl
• 英文别名: 2,2'bis-(propylthio)-6,6'-dinitrobiphenyl；1-Nitro-2-(2-nitro-6-propylsulfanylphenyl)-3-propylsulfanylbenzene
• CAS: 302946-72-1
• 化学式: C₁₈H₂₀N₂O₄S₂
• 分子量: 392.5
• InChiKey: CEQZLMKRTWYNPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-dinitro-6,6'-bis(propylthio)biphenyl 在 盐酸 、 溴 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 2,2'-diamino-3,3',5,5'-tetrabromo-6,6'-bis(propylthio)biphenyl
  参考文献：
  名称：

  Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals

  摘要：

  A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the formation of the Ar-Ar bond except for the synthesis of 1b. All tetra-ortho-substituted biphenyls were prepared via Ullmann coupling reactions. The halogens were introduced after formation of the biphenyl by utilizing the directing properties of the amino group(s). In the case of 3b, a polyhalogenated benzene substrate was used for biphenyl formation via Ullmann coupling.

  DOI：

  10.1021/jo030212p
• 作为产物：
  描述：

  2-溴-3-硝基苯胺 在 氢溴酸 、 铜 作用下， 以 xylene 为溶剂， 反应 20.5h， 生成 2,2'-dinitro-6,6'-bis(propylthio)biphenyl
  参考文献：
  名称：

  Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals

  摘要：

  A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the formation of the Ar-Ar bond except for the synthesis of 1b. All tetra-ortho-substituted biphenyls were prepared via Ullmann coupling reactions. The halogens were introduced after formation of the biphenyl by utilizing the directing properties of the amino group(s). In the case of 3b, a polyhalogenated benzene substrate was used for biphenyl formation via Ullmann coupling.

  DOI：

  10.1021/jo030212p

文献信息

• Formation of 1,10-Disubstituted Benzo[<i>c</i>]cinnolines. Synthesis and Molecular Structure of 1-Amino-10-propylthiobenzo[<i>c</i>]cinnoline and Cyclization to 4-Propylcinnolino[5,4,3][<i>c,d,e</i>][1,2]benzothiazine
  作者：Vladimir Benin、Piotr Kaszynski、Maren Pink、Victor G. Young

  DOI：10.1021/jo0002691

  日期：2000.10.1

  benzo[c]cinnoline derivative 1 was prepared from the trinitrobiphenyl 2. Investigation of the mechanism of ring closure in 2, 5, and 8 revealed a complex reduction-oxidation-cyclization sequence. The mechanism is discussed in light of the stereoelectronic demands of the substituent functionalities. Benzo[c]cinnoline derivative 1 [C15H15N3S, monoclinic, P2(1)/c: a = 7.4063(3) A, b = 10.3739(5) A, c = 16

  由三硝基联苯2制备了第一个1,10-杂二取代的苯并[c] cinnoline衍生物1。对2、5和8中闭环机理的研究揭示了一个复杂的还原-氧化-环化序列。根据取代基官能团的立体电子要求来讨论该机理。苯并[c] cinnoline衍生物1 [C15H15N3S，单斜晶，P2（1）/ c：a = 7.4063（3）A，b = 10.3739（5）A，c = 16.7642（8）A，beta = 91.816（1）度，Z = 4]及其5-N-氧化物7（N5）[C18H18N3OS，三斜晶，Pi：a = 8.1510（7）A，b = 8.6106（7）A，c = 12.102（1）A，α= 86.262 （1）度，β= 83.364（1）度，γ= 74.711（1）度，Z = 4]在结构上得到了表征，并显示出杂环明显的螺旋形扭曲。