ethyl 2-(3-bromophenyl)-5-methyloxazole-4-carboxylate | 1140627-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(3-bromophenyl)-5-methyloxazole-4-carboxylate
• 英文别名: ethyl 2-(3-bromophenyl)-5-methyl-1,3-oxazole-4-carboxylate
• CAS: 1140627-58-2
• 化学式: C₁₃H₁₂BrNO₃
• 分子量: 310.147
• InChiKey: JNNRIOJLKXYUCM-UHFFFAOYSA-N

物化性质

• 沸点：
  398.2±52.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 ethyl 2-(3-bromophenyl)-5-methyloxazole-4-carboxylate 在 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 ethyl 5-methyl-2-(3-(morpholin-4-yl)phenyl)-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

  摘要：

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.021
• 作为产物：
  描述：

  ethyl 2-[(3-bromobenzoyl)amino]-3-oxobutanoate 在 碘 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-(3-bromophenyl)-5-methyloxazole-4-carboxylate
  参考文献：
  名称：

  Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

  摘要：

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.021

文献信息

• A Highly Efficient Heterogeneous Copper-Catalyzed Oxidative Cyclization of Benzylamines and 1,3-Dicarbonyl Compounds To Give Trisubstituted Oxazoles
  作者：Li Wei、Shengyong You、Yuxin Tuo、Mingzhong Cai

  DOI：10.1055/s-0037-1610710

  日期：2019.8

  yields. This heterogeneous copper catalyst can be facilely prepared via a simple two-step procedure from readily available and inexpensive reagents and exhibits a slightly higher activity than Cu(OAc)2. MCM-41-2N-Cu(OAc)2 is also easy to recover and can be recycled up to eight times with almost consistent activity. The reaction is the first example of heterogeneous copper-catalyzed intermolecular cyclization

  抽象的 通过使用3-（2-氨基乙基氨基）丙基官能化的MCM-41固定铜（II）配合物[MCM-41-2N-Cu]，实现苄胺和1,3-二羰基化合物之间铜的多相铜级联氧化环化反应（OAc）2 ]作为催化剂，t- BuOOH（TBHP）作为氧化剂，以碘为添加剂，在温和的条件下，可产生多种2,4,5-三取代的恶唑，收率大多良好至极佳。可以通过简单的两步程序轻松地从容易获得的廉价试剂制备这种多相铜催化剂，并且其活性比Cu（OAc）2略高。MCM-41-2N-Cu（OAc）2回收也很容易，可以回收八次，几乎保持一致的活性。该反应是用于构建多取代的恶唑的非均相铜催化的分子间环化的第一个实例。 通过使用3-（2-氨基乙基氨基）丙基官能化的MCM-41固定铜（II）配合物[MCM-41-2N-Cu]，实现苄胺和1,3-二羰基化合物之间铜的多相铜级联氧化环化反应（OAc）2 ]作为催化剂，t- BuOOH（T