1,2,3-三溴-4-硝基苯 | 96558-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2,3-三溴-4-硝基苯
• 英文名称: 1,2,3-tribromo-4-nitrobenzene
• 英文别名: 2,3,4-tribromonitrobenzene；1,2,3-tribromo-4-nitro-benzene；1,2,3-Tribrom-4-nitro-benzol；1,2,3-Tribromo-4-nitrobenzene
• CAS: 96558-72-4
• 化学式: C₆H₂Br₃NO₂
• 分子量: 359.799
• InChiKey: PFIPDHZFOSAFIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2,3-三溴-4-硝基苯 在 盐酸 、 tin(ll) chloride 作用下， 生成 2,3,4-tribromoaniline
  参考文献：
  名称：

  Koerner; Contardi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 II, p. 585

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二溴苯胺 在 亚硝酸特丁酯 、 硝酸 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 2.0h， 生成 1,2,3-三溴-4-硝基苯
  参考文献：
  名称：

  Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling

  摘要：

  An efficient total synthesis of the annulated indole natural product(+/-)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.125

文献信息

• Synthesis of Polybrominated Diphenyl Ethers and Their Capacity to Induce CYP1A by the Ah Receptor Mediated Pathway
  作者：Guosheng Chen、Alexandre D. Konstantinov、Brock G. Chittim、Elizabeth M. Joyce、Niels C. Bols、Nigel J. Bunce

  DOI：10.1021/es0107475

  日期：2001.9.1

  Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyresorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10(-2)-10(-5) times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition Sequence.
• Koerner; Contardi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5>15 II, p. 583
  作者：Koerner、Contardi

  DOI：——

  日期：——
• Koerner; Contardi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 II, p. 585
  作者：Koerner、Contardi

  DOI：——

  日期：——
• Liedholm, Brita, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 10, p. 877 - 884
  作者：Liedholm, Brita

  DOI：——

  日期：——
• Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling
  作者：Nalin Chandrasoma、Neil Brown、Allen Brassfield、Alok Nerurkar、Susana Suarez、Keith R. Buszek

  DOI：10.1016/j.tetlet.2012.11.125

  日期：2013.2

  An efficient total synthesis of the annulated indole natural product(+/-)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.