2-(4-溴苯基)-咪唑并[1,2-A]嘧啶 | 56921-85-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-溴苯基)-咪唑并[1,2-A]嘧啶
• 英文名称: 2-(4-bromophenyl)imidazo[1,2-a]pyrimidine
• CAS: 56921-85-8
• 化学式: C₁₂H₈BrN₃
• mdl: MFCD01103134
• 分子量: 274.12
• InChiKey: MUBZZRZIBNKULO-UHFFFAOYSA-N

物化性质

• 熔点：
  279℃
• 密度：
  1.58

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯基)-咪唑并[1,2-A]嘧啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以87%的产率得到5-(对溴苯基)-2-氨基咪唑
  参考文献：
  名称：

  Microwave-assisted synthesis of substituted 2-amino-1H-imidazoles from imidazo[1,2-a]pyrimidines

  摘要：

  An efficient method for the synthesis of mono- and disubstituted 2-amino-1H-imidazoles via microwave-assisted hydrazinolysis of substituted imidazo[1,2-a]pyrimidines is reported. This protocol avoids strong acidic conditions and is superior to the classical cyclocondensation of alpha-haloketones with N-acetylguanidine. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.128
• 作为产物：
  描述：

  4-溴苯乙酮 以 乙腈 为溶剂， 反应 6.0h， 生成 2-(4-溴苯基)-咪唑并[1,2-A]嘧啶
  参考文献：
  名称：

  Aggarwal, Ranjana; Sumran, Garima, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 12, p. 2690 - 2695

  摘要：

  DOI：

文献信息

• Synthesis and Antibacterial Activity of Some Imidazo(1,2-a)pyrimidine Derivatives.
  作者：Yveline RIVAL、Gerard GRASSY、Georges MICHEL

  DOI：10.1248/cpb.40.1170

  日期：——

  A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The "in vitro" antibacterial activity of these compounds and their corresponding alpha-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.

  合成了75种咪唑并[1,2-a]嘧啶衍生物。据报道，这些化合物及其相应的α-溴代酮对多种革兰氏（+），革兰氏（-）细菌和分枝杆菌属物种具有“体外”抗菌活性。一些制备的衍生物表现出有效的抗微生物活性。
• TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-<i>a</i>]pyridines with Fluorinated Alcohols
  作者：Dhananjay S. Nipate、Sonam Jaspal、Vikki N. Shinde、Krishnan Rangan、Anil Kumar

  DOI：10.1021/acs.orglett.1c00031

  日期：2021.2.19

  A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)–H and C(sp2)–H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation

  已经开发了一种简单高效的无金属方法，用于通过TEMPO介导的C（sp 3）–H和C（sp 2）–H键交叉脱氢偶联将吲哚和咪唑并[1,2- a ]吡啶进行羟基氟烷基化氟化醇和吲哚。该方案显示出广泛的底物范围，提供了良好的羟基氟烷基化产物收率，并且适合规模扩大。机理研究表明该自由基途径的参与。
• [EN] SUBSTITUTED 2-NAPHTHOIC ACIDS AS ANTAGONISTS OF GPR105 ACTIVITY<br/>[FR] ACIDES 2-NAPHTOÏQUE SUBSTITUÉS EN TANT QU'ANTAGONISTES DE L'ACTIVITÉ DE GPR105
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2009070873A1

  公开（公告）日：2009-06-11

  Substituted 2-naphthoic acids of structural formula I are effective as antagonists of the biological activity of GPR105 protein. They are useful for the treatment, control or prevention of disorders responsive to antagonism of this receptor, such as diabetes, particularly, Type 2 diabetes, insulin resistance, hyperglycemia, lipid disorders, obesity, atherosclerosis, and conditions associated with the Metabolic Syndrome.

  结构式I中的2-萘甲酸替代物对GPR105蛋白的生物活性具有拮抗作用。它们可用于治疗、控制或预防对该受体拮抗有响应的疾病，如糖尿病，特别是2型糖尿病，胰岛素抵抗，高血糖，脂质紊乱，肥胖，动脉粥样硬化以及与代谢综合征相关的疾病。
• Hypervalent Iodine(III) Sulfonate Mediated Synthesis of 2-Arylimidazo[1,2-<i>a</i>]Pyrimidines in Liquid PEG-400
  作者：Hui-Ting Cheng、Rei-Sheu Hou、Huey-Min Wang、Iou-Jiun Kang、Pei-Ying Lin、Ling-Ching Chen

  DOI：10.1002/jccs.200900094

  日期：2009.6

  PEG‐400[poly(ethylene glycol‐400)] is used as a “green” recyclable solvent in the one‐pot synthesis of 2‐arylimidazo[1,2‐a]pyrimidines by reaction with ketones, [hydroxyl(2,4‐dinitrobenzenesulfonyloxy)‐iodo]benzene (HDNIB), and 2‐aminopyrimidine. Significant rate enhancements and improved yields have been observed.

  PEG-400 [聚（乙二醇-400）]在与酮[羟基（2,4,4）反应的单罐合成2-芳基咪唑[1,2- a ]嘧啶中用作“绿色”可回收溶剂-二硝基苯磺酰氧基）-碘]苯（HDNIB）和2-氨基嘧啶。已经观察到速率显着提高和产量提高。
• Synthesis of Bridgehead Nitrogen Heterocycles on a Solid Surface
  作者：Shashikanth Ponnala、S. T. V. S. Kiran Kumar、Bashir A. Bhat、Devi Prasad Sahu

  DOI：10.1081/scc-200051674

  日期：2005.4.1

  Abstract Bridgehead nitrogen heterocycles were synthesized from heteroaromatic amidines and cyclic or acyclic α‐bromoketones under solvent‐free conditions at room temperature on a solid surface in excellent yields, which are higher than those obtained with hitherto‐known methods of syntheses. #CDRI Communication No. 6545.

  摘要 桥头氮杂环是由杂芳脒和环状或非环状 α-溴酮在室温下无溶剂条件下在固体表面上以优异的收率合成的，收率高于迄今为止已知的合成方法。#CDRI 通讯第 6545 号。