6-溴-3’-硝基黄酮 | 187932-50-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-溴-3’-硝基黄酮
• 中文别名: 6-溴-3'-硝基黄酮
• 英文名称: 6-Bromo-3'-nitroflavone
• 英文别名: 6-bromo-2-(3-nitrophenyl)chromen-4-one
• CAS: 187932-50-9
• 化学式: C₁₅H₈BrNO₄
• 分子量: 346.137
• InChiKey: IPHSQMSRIWZULE-UHFFFAOYSA-N

物化性质

• 熔点：
  243-244 °C(Solv: ethanol (64-17-5))
• 沸点：
  490.9±45.0 °C(Predicted)
• 密度：
  1.669±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、乙酸乙酯（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-溴-3’-硝基黄酮 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 生成 2-(3-Aminophenyl)-6-bromo-4H-1-benzopyran-4-one
  参考文献：
  名称：

  使用 1D 和 2D 核磁共振光谱法合成和结构解析五个系列的氨基黄酮

  摘要：

  通过两种不同的方法合成了 26 种新的氨基黄酮，并使用广泛的 1D（1H、13C）和 2D NMR 光谱研究（COSY、HSQC 和 HMBC 实验）完成了结构解析。版权所有 © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.1895
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 在 氢氧化钾 、 硫酸 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 生成 6-溴-3’-硝基黄酮
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0

文献信息

• Synthetic Flavonoids and Pharmaceutical Compositions and Therapeutic Methods of Treatment of HIV infection and other pathologies
  申请人：Redda Kinfe

  公开号：US20120264820A1

  公开（公告）日：2012-10-18

  A compound, pharmaceutical composition and method for the treatment of mammals wherein the active therapeutic agent is a compound having the structure: wherein: R 1 is an electronegative substituent, R 2 is R 1 or alkyl, R 3 is H or O-alkyl, R 4 and R 5 are the same or different and are alkyl and R 6 is H or OH.

  一种用于治疗哺乳动物的化合物、药物组合物和方法，其中活性治疗剂是具有以下结构的化合物：其中：R1是一个电负取代基，R2是R1或烷基，R3是H或O-烷基，R4和R5相同或不同，为烷基，R6是H或OH。
• Synthetic Flavonoids and Pharmaceutical Compositions and Therapeutic Methods of Treatment of Cancer and other Pathologies
  申请人：Redda Kinfe

  公开号：US20090312407A1

  公开（公告）日：2009-12-17

  A compound, pharmaceutical composition and method for the treatment of mammals wherein the active therapeutic agent is a compound having the structure: wherein: R 1 is an electronegative substituent, R 2 is R 1 or alkyl, R 3 is H or O-alkyl, R 4 and R 5 are the same or different and are alkyl and R 6 is H or OH.

  一种化合物、药物组合物和治疗哺乳动物的方法，其中活性治疗剂为具有以下结构的化合物：其中：R1是电负性取代基，R2是R1或烷基，R3是H或O-烷基，R4和R5相同或不同，是烷基，R6是H或OH。
• Methods of treating benzodiazepine site (BZD-S) associated syndromes using 2' hydroxyflavonoids
  申请人：Naturon Limited

  公开号：US20040034092A1

  公开（公告）日：2004-02-19

  Methods for preventing or for treating benzodiazepine site (BZD-S) associated syndromes comprising administering 2′ hydroxyflavone and flavone derivatives thereof which contain a hydroxyl group at the 2′ position to a patient in need thereof in an effective dose. Methods for extracting certain of the compounds from plant material are also described.

  预防或治疗苯并二氮杂卓部位（BZD-S）相关综合症的方法，包括以有效剂量给需要的病人服用2′羟基黄酮及其黄酮衍生物，这些衍生物在2′位置含有羟基。还描述了从植物材料中提取某些化合物的方法。
• Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
  作者：Mariel Marde、Juan Zinczuk、María I. Colombo、Cristina Wasowski、Haydee Viola、Claudia Wolfman、Jorge H. Medina、Edmundo A. Rúveda、Alejandro C. Paladini

  DOI：10.1016/s0960-894x(97)00343-0

  日期：1997.8

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.
• A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation
  作者：Michael Lorenz、M. Shahjahan Kabir、James M. Cook

  DOI：10.1016/j.tetlet.2009.12.107

  日期：2010.2

  A general route for the synthesis of biologically important flavones is reported via a two step sequence employing a catalytic Wacker-Cook oxidation(4b) as the key step. (C) 2009 Elsevier Ltd. All rights reserved.