3-(2-bromoacetyl)-6-nitro-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(2-bromoacetyl)-6-nitro-2H-chromen-2-one
• 英文别名: 3-(2-Bromoacetyl)-6-nitrochromen-2-one
• 化学式: C₁₁H₆BrNO₅
• 分子量: 312.076
• InChiKey: YIKVQIFIDKXMAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-bromoacetyl)-6-nitro-2H-chromen-2-one 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 13.0h， 生成 1-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(p-tolyl)urea
  参考文献：
  名称：

  Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

  摘要：

  A newly series of coumarylthiazole derivatives containing aryl urea/thiourea groups were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized compounds exhibited inhibitory activity to both cholinesterases. Among them, 1-(4-(8-methoxy-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(4-chlorophenyl)thiourea (f8, IC50 = 4.58 mu M) was found to be the most active compound against AChE, and 1-(4-fluorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e31) exhibited the strongest inhibition against BuChE with IC50 value of 4.93 mu M, which was 3.5-fold more potent than that of galantamine. The selectivity of f8 and e31 were 2.64 and 0.04, respectively. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for antioxidant activity. Among them, f8, f4 and f6 (IC50 = 1.64, 1.82 and 2.69 mu M, respectively) showed significantly better ABTS cation radical scavenging ability than standard quercetin (IC50 = 15.49 mu M). (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.002
• 作为产物：
  描述：

  3-乙酰基-6-硝基-2H-苯并吡喃-2-酮 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 生成 3-(2-bromoacetyl)-6-nitro-2H-chromen-2-one
  参考文献：
  名称：

  新型糖基香豆素噻唑衍生物的合成及抗乙酰胆碱酯酶活性

  摘要：

  通过糖基硫脲与3-溴乙酰基香豆素在乙醇中的环化和缩合反应，合成了11种糖基香豆基噻唑衍生物。优化了反应条件，并获得了良好的收率（80％–95％）。所有新产品的结构均通过IR，1 H和13 C NMR以及HRMS（电喷雾电离）确定。在体外乙酰胆碱酯酶抑制这些新化合物的活性由Ellman氏方法进行测试。其中，N-（2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β - D-吡喃吡喃糖基）-4-（6-硝基香豆基）-1,3-噻唑-2-胺在体外显示出最佳活性AChE抑制率为58％，IC 50值为12±0.38μg/ mL。

  DOI：

  10.1177/1747519820948358

文献信息

• Tetrabutylammonium tribromide: an effective green reagent for the one-pot reaction of 3-acetyl-2H-chromen-2-ones with o-phenylenediamines
  作者：Kotthireddy Kavitha、Devulapally Srikrishna、Pramod Kumar Dubey、Pasula Aparna

  DOI：10.24820/ark.5550190.p010.655

  日期：——

  with o-phenylenediamines using tetrabutylammonium tribromide (TBATB) to obtain 3-(quinoxalin-2-yl)2H-chromen-2-ones in one-pot. Alternatively, a step-wise method has also been demonstrated for the synthesis of 3-(quinoxalin-2-yl)-2H-chromen-2-ones, where 3-acetyl-2H-chromen-2-ones has first treated with TBATB to give 3-(2-bromoacetyl)-2H-chromen-2-one followed by its nucleophilic substitution reaction

  已经概述了使用四丁基三溴化铵 (TBATB) 使 3-乙酰基-2H-chromen-2ones 与邻苯二胺反应获得 3-(quinoxalin-2-yl)2H-chromen-2-ones 的有效且完全绿色的方法在一锅中。或者，也证明了一种用于合成 3-(quinoxalin-2-yl)-2H-chromen-2-ones 的逐步方法，其中 3-acetyl-2H-chromen-2-ones 首先用 TBATB 处理得到 3-(2-bromoacetyl)-2H-chromen-2-one，然后与邻苯二胺发生亲核取代反应。使用聚乙二醇-600 (PEG-600) 作为溶剂介质、温和的反应条件和易于分离的产物是这种合成的额外优势。已经比较了一锅法和逐步法的反应产率，发现一锅法合成更优。
• An Efficient, Multicomponent Synthesis of Pyrazolyl Triazolo Thiadiazinyl Chromen - 2 - Ones
  作者：Sreenu Pavurala、Rajeswar Rao Vedula

  DOI：10.1002/jhet.2027

  日期：2015.1

  One‐pot synthesis of 3‐(3‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)‐2H‐chromen‐2‐ones was achieved via the multicomponent reaction of purpald, acetyl acetone, and different derivatives of 3‐(2‐bromo‐acetyl)‐2H‐chromen‐2‐one in absolute ethanol. All the synthesized compounds were characterized by analytical and spectral data.

  一锅合成3-（3-（3,5-二甲基-1 H-吡唑-1-基）-7 H- [1,2,4]三唑[3,4- b ] [1,3， 4]噻二嗪-6-基）-2 H-铬-2-基团是通过紫红色，乙酰丙酮和3-（2-溴-乙酰基）-2 H-铬烯-2-基的不同衍生物进行多组分反应而制得的在无水乙醇中一种。所有合成的化合物均通过分析和光谱数据表征。
• One-Pot Three-Component Synthesis of Pyrazolyl-thiadiazinyl-2<i>H</i>-chromen-2-one Derivatives
  作者：Sreenu Pavurala、Krishnaiah Vaarla、Rajeswar Rao Vedula

  DOI：10.1002/jhet.2262

  日期：2015.9

  An efficient novel one‐pot synthesis of pyrazolyl‐thiadiazinyl‐2H‐chromen‐2‐ones. In this process, an equimolar mixture of substituted 3‐(2‐bromoacetyl)‐2H‐chromen‐2‐ones, thiocarbohydrazide and pentane‐2,4‐dione were taken in absolute ethanol. All these synthesized compounds were characterized by their analytical and spectral data.

  一种高效，新颖的一锅合成吡唑基-噻二嗪基-2 H-铬n-2-酮。在此过程中，将取自3-（2-溴乙酰基）-2- H-铬n-2-酮，硫代碳酰肼和戊烷-2,4-二酮的等摩尔混合物置于无水乙醇中。所有这些合成的化合物均以其分析和光谱数据为特征。
• An Efficient Synthesis of Quinoxalines under Catalyst-Free and Microwave-Irradiation Conditions
  作者：Jian-Feng Zhou、Gui-Xia Gong、Li-Tao An、Yu Liu、Feng-Xia Zhu、Yu-Lan Zhu、Shun-Jun Ji

  DOI：10.1055/s-0028-1087280

  日期：——

  A series of quinoxaline derivatives was synthesized by the reaction of 3-(ω-bromoacetyl)coumarins with substituted 1,2-diaminobenzenes in the absence of a catalyst under microwave conditions. Reasonable yields of the products, environmentally benign and convenient workup are the advantages of this method.

  在无催化剂的微波条件下，通过 3-(Ï-溴乙酰基)香豆素与取代的 1,2-二氨基苯的反应合成了一系列喹喔啉衍生物。该方法具有产率合理、对环境无害和操作简便等优点。
• Synthesis of 3-(2-(4,5-Dihydro-3,5-diphenylpyrazol-1-yl)thiazol-4-yl)-2<i>H</i>-chromen-2-one Derivatives via Multicomponent Approach
  作者：Sreenu Pavurala、Rajeswar Rao Vedula

  DOI：10.1080/00397911.2013.796522

  日期：2014.3.4

  Abstract An efficient synthesis of 3-(2-(4,5-dihydro-3,5-diphenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one derivatives by a simple, atom-economical, and multicomponent reaction of chalcones, thiosemicarbazide, and 3-(2-bromoacetyl) coumarins in the presence of aqueous sodium hydroxide in refluxing ethanol is reported. The structures of newly prepared compounds have been confirmed by their analytical

  摘要 通过简单的、原子经济的、有效的合成 3-(2-(4,5-dihydro-3,5-diphenylpyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one 衍生物，报道了在氢氧化钠水溶液存在下，在回流乙醇中，查耳酮、氨基硫脲和 3-（2-溴乙酰基）香豆素的多组分反应。新制备的化合物的结构已通过其分析和光谱（IR、1HNMR、13CNMR 和质量）数据得到证实。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要