3,3',5,5'-tetrabromo-2'-(trifluoroacetylamino)-2-nitrobiphenyl | 642068-39-1

• 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: 3,3',5,5'-tetrabromo-2'-(trifluoroacetylamino)-2-nitrobiphenyl
• 英文别名: N-[2,4-dibromo-6-(3,5-dibromo-2-nitrophenyl)phenyl]-2,2,2-trifluoroacetamide
• CAS: 642068-39-1
• 化学式: C₁₄H₅Br₄F₃N₂O₃
• 分子量: 625.817
• InChiKey: MRYMPAPAVIYJTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3',5,5'-tetrabromo-2'-(trifluoroacetylamino)-2-nitrobiphenyl 在 potassium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 以88%的产率得到2-amino-3,3',5,5'-tetrabromo-2'-nitrobiphenyl
  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-amino-3,3',5,5'-tetrabromo-2'-(trifluoroacetylamino)biphenyl 在 双氧水 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到3,3',5,5'-tetrabromo-2'-(trifluoroacetylamino)-2-nitrobiphenyl
  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

• Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals
  作者：Jason T. Manka、Fengli Guo、Jianping Huang、Huiyong Yin、John M. Farrar、Monika Sienkowska、Vladimir Benin、Piotr Kaszynski

  DOI：10.1021/jo030212p

  日期：2003.12.1

  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.