2-(chloromethyl)-4,5-diphenyloxazole | 33161-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(chloromethyl)-4,5-diphenyloxazole
• 英文别名: 2-Chlormethyl-4,5-diphenyl-oxazol；2-Chloromethyl-4,5-diphenyl-oxazole；2-(chloromethyl)-4,5-diphenyl-1,3-oxazole
• CAS: 33161-99-8
• 化学式: C₁₆H₁₂ClNO
• mdl: MFCD12463326
• 分子量: 269.73
• InChiKey: PBUULIMICIROPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(chloromethyl)-4,5-diphenyloxazole 在 盐酸 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 35.5h， 生成 奥沙普秦
  参考文献：
  名称：

  扩展的恶唑的合成II：2-（卤甲基）-4，5-二芳基恶唑的反应歧管。

  摘要：

  2-（卤甲基）-4，5-二苯基恶唑是有效的反应性支架，可用于2-位的合成修饰。通过取代反应，氯甲基类似物用于制备许多2-烷基氨基-，2-烷硫基和2-烷氧基-（甲基）恶唑。2-溴甲基类似物为氯甲基化合物提供了更具反应性的替代物，可用于稳定的（丙二酸酯）碳负离子的C-烷基化，如氧杂丙嗪的简明合成所举例说明的那样。

  DOI：

  10.1016/j.tetlet.2016.01.016
• 作为产物：
  描述：

  2-oxo-1,2-diphenylethyl-2-chloroacetate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-(chloromethyl)-4,5-diphenyloxazole
  参考文献：
  名称：

  1,2,3-Triazole-based inhibitors of Porphyromonas gingivalis adherence to oral streptococci and biofilm formation

  摘要：

  The development and use of small-molecule inhibitors of the adherence of Porphyromonas gingivalis to oral streptococci represents a potential therapy for the treatment of periodontal disease as these organisms work in tandem to colonize the oral cavity. Earlier work from these laboratories demonstrated that a small synthetic peptide was an effective inhibitor of the interaction between P. gingivalis and Streptococcus gordonii and that a small-molecule peptidomimetic would provide a more stable, less expensive and more effective inhibitor. An array of 2-(azidomethyl)- and 2-(azidophenyl)-4,5-diaryloxazoles having a full range of hydrophobic groups were prepared and reacted with substituted arylacetylenes to afford the corresponding 'click' products. The title compounds were evaluated for their ability to inhibit P. gingivalis' adherence to oral streptococci and several were found to be inhibitory in the range of (IC50) 5.3-67 mu M. (C) 2016 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.orgilicensesiby-nc-nd/4.0/).

  DOI：

  10.1016/j.bmc.2016.08.059

文献信息

• Iron-Catalyzed Cycloaddition of Amides and 2,3-Diaryl-2<i>H</i>-azirines To Access Oxazoles via C–N Bond Cleavage
  作者：Mi-Na Zhao、Gui-Wan Ning、De-Suo Yang、Ming-Jin Fan、Sheng Zhang、Peng Gao、Li-Fang Zhao

  DOI：10.1021/acs.joc.0c02843

  日期：2021.2.5

  A novel and efficient iron-catalyzed cycloaddition reaction using readily available 2,3-diaryl-2H-azirines and primary amides is reported. A wide range of trisubstituted oxazoles could be achieved in good yields with good functional group compatibility. In this transformation, two C–N bonds were cleaed and new C–N and C–O bonds were formed.

  使用容易获得的2,3-二芳基-2-一种新颖和有效的铁-催化的环加成反应ħ -azirines和伯酰胺进行报告。可以以良好的收率和良好的官能团相容性获得各种三取代的恶唑。在此转变中，两个C–N键被切割，并形成了新的C–N和C–O键。
• Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds
  作者：Pravin C. Patil、Frederick A. Luzzio、Donald R. Demuth

  DOI：10.1016/j.tetlet.2014.11.014

  日期：2015.6

  New routes to 2, 4, 5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of symmetrical and non-symmetrical acyloins were cyclized using an ammonium acetate/acetic acid protocol

  建立了形成2、4、5-三取代的恶唑的新途径，从而通过起始的不对称酰基胞苷的结构建立了取代模式。通过改进先前描述的方法制备2-氯甲基-4，5-二取代的恶唑，其中使用乙酸铵/乙酸方案将对称和不对称酰基的氯乙酰基酯环化。进行取代后，然后在温和条件下通过取代安装叠氮化物部分。尽管需要二溴化和碘化的苯基恶唑进行进一步的合成修饰，但发现环化反应对原料中卤素的相对位置非常敏感。
• ‘Second-generation’ 1,2,3-triazole-based inhibitors of <i>Porphyromonas gingivalis</i> adherence to oral streptococci and biofilm formation
  作者：Pravin C. Patil、Jinlian Tan、Donald R. Demuth、Frederick A. Luzzio

  DOI：10.1039/c8md00405f

  日期：——

  This study details the design, synthesis and bioassay of ‘click’ peptidomimetic compounds which inhibit the adherence of P. gingivalis to S. gordonii, a primary step toward pathogenic colonization of the subgingival pocket.

  这项研究详细介绍了设计、合成和生物测定“点击”肽类模拟化合物，这些化合物抑制了牙龈脓毒性链球菌（P. gingivalis）附着到戈登氏链球菌（S. gordonii），这是病原体在龈下袋中定植的主要步骤。
• 2-Aminomethyl- and 2-(2-aminoethyl)-substituted 4,5-diphenyloxazoles
  申请人：——

  公开号：US04020082A1

  公开（公告）日：1977-04-26

  2-Aminomethyl- and 2-(2-aminoethyl)-substituted 4,5-diphenyloxazoles of the general formula ##STR1## and salts thereof with non-toxic organic or inorganic acids having antiphlogistic, analgesic, anti-aggregant and local anaesthetic properties with low toxicity are provided, as well as processes for preparing them.

  提供了通式为##STR1##的2-氨甲基和2-(2-氨乙基)-取代的4,5-二苯基噁唑及其与具有抗炎、镇痛、抗聚集和局部麻醉作用的低毒性非毒性有机或无机酸盐，以及其制备方法。
• [EN] ANTI-BIOFILM COMPOUNDS<br/>[FR] COMPOSÉS ANTI-BIOFILM
  申请人：UNIV LOUISVILLE RES FOUND INC

  公开号：WO2020023318A1

  公开（公告）日：2020-01-30

  The present invention provides non-peptide compounds that mimic the streptococcal SspB Adherence Region (BAR) and function as inhibitors of P. gingivalis adherence to streptococci. The invention also provides methods of making and using the inhibitors.

  本发明提供了模拟链球菌SspB粘附区域（BAR）的非肽化合物，并作为抑制牙龈链球菌粘附到链球菌的抑制剂。该发明还提供了制备和使用这些抑制剂的方法。