2-(苄氧基)-1-溴-3-硝基苯 | 688363-79-3

• 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: 2-(苄氧基)-1-溴-3-硝基苯
• 中文别名: 2-(苯基氧基)-1-溴-3-硝基苯；布瓦西坦中间体
• 英文名称: 2-(benzyloxy)-1-bromo-3-nitrobenzene
• 英文别名: 1-bromo-3-nitro-2-phenylmethoxybenzene
• CAS: 688363-79-3
• 化学式: C₁₃H₁₀BrNO₃
• 分子量: 308.131
• InChiKey: IJAMXMAVDDCHHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密封。

反应信息

• 作为反应物：
  描述：

  2-(苄氧基)-1-溴-3-硝基苯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-氨基吩恶嗪酮
  参考文献：
  名称：

  Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives

  摘要：

  2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H-2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine I is disclosed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.080
• 作为产物：
  描述：

  硝苯酚 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 生成 2-(苄氧基)-1-溴-3-硝基苯
  参考文献：
  名称：

  Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives

  摘要：

  2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H-2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine I is disclosed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.080

文献信息

• [EN] INTRACELLULAR RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS MODULATEURS DE RÉCEPTEURS INTRACELLULAIRES ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CEUX-CI
  申请人：LIGAND PHARM INC

  公开号：WO2006019716A1

  公开（公告）日：2006-02-23

  This invention relates to compounds of Formula I, II or III with the definitions of R1-R10 according to claim 1 that bind to intracellular receptors and/or modulate activity of intracellular receptors, and to methods for making and using such compounds.

  这项发明涉及具有根据权利要求1中R1-R10的定义的化合物I、II或III，这些化合物与细胞内受体结合和/或调节细胞内受体活性，并涉及制备和使用这类化合物的方法。
• [EN] FARNESOID X RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RÉCEPTEUR DE FARNÉSOÏDE X
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009005998A1

  公开（公告）日：2009-01-08

  The present invention relates to famesoid X receptors (FXR, NR1H4) FXR is a member of the nuclear receptor class of ligand-activate transcription factors More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceutical formulations comprising such compounds, and therapeutic use of the same Novel isoxazole compounds are disclosed as part of pharmaceutical compositions for the treatment of a condition mediated by decreased FXR activity, such as obesity, diabetes, cholestatic liver disease, liver fibrosis, and metabolic syndrome

  本发明涉及法内索德X受体（FXR，NR1H4）。FXR是配体激活的转录因子核受体类的一个成员。更具体地说，本发明涉及作为FXR激动剂的化合物，包含该化合物的药物制剂，以及同一治疗用途。新颖的异恶唑化合物被披露作为药物组合物的一部分，用于治疗由FXR活性降低介导的状况，如肥胖、糖尿病、胆汁淤积性肝病、肝纤维化和代谢综合征。
• Preparation process of an agonist of the thrombopoietin receptor
  申请人：Esteve Química, S.A.

  公开号：EP2799425A1

  公开（公告）日：2014-11-05

  It relates to a preparation process of 2'-(benzyloxy)-3'-nitro-1,1'-biphenyl-3-carboxylic acid or a salt thereof comprising reacting 2-(benzyloxy)-1-bromo-3-nitrobenzene with a either 3-carboxyphenylboronic acid or a salt thereof or a (C1-C4)-alkyl ester thereof in the presence of Pd(OAc)2, tricyclohexylphosphine, a base, an appropriate solvent, and at an appropriate temperature; if appropriate, submitting the compound thus obtained to a hydrolysis reaction; and isolating the compound thus obtained in form of a salt of compound of formula (VI) or in form of the free acid by adding an acid. It also comprises the further preparation to eltrombopag or its salts from the new intermediate thus obtained by subsequent reduction of the nitro group and deprotection of the phenol, conversion of the amine intermediate obtained in a diazonium derivative, and either (1) subsequent reaction with ethyl acetoacetate and with (3,4-dimethylphenyl)hydrazine or a salt thereof, occurring the pyrazole ring formation by intermolecular cyclization, or (2) introduction of the pyrazole ring by reaction with 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one.

  它涉及到2'-(苄氧基)-3'-硝基-1,1'-联苯-3-羧酸或其盐的制备过程，包括在Pd(OAc)2、三环己基膦、碱、适当溶剂和适当温度下，将2-(苄氧基)-1-溴-3-硝基苯与3-羧基苯硼酸或其盐或其(C1-C4)烷基酯之一反应；如适当，将得到的化合物提交给水解反应；通过加入酸，将得到的化合物以化合物式(VI)的盐形式或自由酸形式分离出来。它还包括从所得的新中间体中进一步制备厄洛替尼或其盐，方法是通过连续还原硝基团和去保护酚基，将获得的胺中间体转化为重氮衍生物，然后（1）与乙酰乙酸乙酯和（3,4-二甲基苯基）肼或其盐反应，通过分子间环化形成吡唑环，或者（2）通过与1-(3,4-二甲基苯基)-3-甲基-3-吡唑啉-5-酮反应引入吡唑环。
• [EN] PREPARATION PROCESS OF AN AGONIST OF THE THROMBOPOIETIN RECEPTOR<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN AGONISTE DU RÉCEPTEUR DE LA THROMBOPOÏÉTINE
  申请人：ESTEVE QUÍMICA S A

  公开号：WO2014177517A1

  公开（公告）日：2014-11-06

  It relates to a preparation process of 2'-(benzyloxy)-3'-nitro-1,1'-biphenyl-3- carboxylic acid or a salt thereof comprising reacting 2-(benzyloxy)-1-bromo- 3-nitrobenzene with a either 3-carboxyphenylboronic acid or a salt thereof or a (C1-C4)-alkyl ester thereof in the presence of Pd(OAc)2, tricydohexylphosphine, a base, an appropriate solvent, and at an appropriate temperature; if appropriate, submitting the compound thus obtained to a hydrolysis reaction; and isolating the compound thus obtained in form of a salt of compound of formula (VI) or in form of the free acid by adding an acid. It also comprises the further preparation to eltrombopag or its salts from the new intermediate thus obtained by subsequent reduction of the nitro group and deprotection of the phenol, conversion of the amine intermediate obtained in a diazonium derivative, and either (1) subsequent reaction with ethyl acetoacetate and with (3,4-dimethylphenyl)hydrazine or a salt thereof, occurring the pyrazole ring formation by intermolecular cyclization, or (2) introduction of the pyrazole ring by reaction with 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one.

  这段文字描述了2'-(苄氧基)-3'-硝基-1,1'-联苯-3-羧酸或其盐的制备过程，包括在Pd(OAc)2、三环己基膦、一种碱、适当的溶剂和适当的温度下，将2-(苄氧基)-1-溴-3-硝基苯与3-羧基苯硼酸或其盐或其(C1-C4)烷基酯之一反应；如适当，将得到的化合物提交给水解反应；通过加入酸，以化合物的盐的形式或自由酸的形式分离得到的化合物，其为化合物的公式(VI)的盐或自由酸形式。它还包括从所得的新中间体中进一步制备厄洛替尼或其盐，方法为随后还原硝基团并去保护酚基，将获得的胺中间体转化为重氮衍生物，然后(1)与乙酰乙酸乙酯和(3,4-二甲基苯基)肼或其盐反应，通过分子间环化发生吡唑环形成，或者(2)通过与1-(3,4-二甲基苯基)-3-甲基-3-吡唑啉-5-酮反应引入吡唑环。
• 一种用于治疗特发性血小板减少性紫癜的药物艾曲波帕的制备方法
  申请人：孙婷婷

  公开号：CN107915678A

  公开（公告）日：2018-04-17

  本发明公开了一种用于治疗特发性血小板减少性紫癜的药物艾曲波帕的制备方法，所述艾曲波帕的化学名称为3‑(2Z)‑2‑[1‑(3,4‑二甲苯基)‑3‑甲基‑5‑氧代‑1,5‑二氢‑4H‑吡唑‑4‑亚基]肼基}‑2‑羟基‑3‑联苯基甲酸‑2‑氨基乙醇盐；本发明制备工艺过程简洁，原料易得，避免使用含有剧毒的碘甲烷，经济环保，有利于实现工业化，可促进艾曲波帕原料药的经济技术发展，降低了生产成本，适于大批量生产。