2-(2,4-dichlorophenyl)-5-phenyloxazole | 108011-90-1

• 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-(2,4-dichlorophenyl)-5-phenyloxazole
• 英文别名: 2-(2,4-Dichlorphenyl)-5-phenyloxazol；2-(2,4-dichlorophenyl)-5-phenyl-1,3-oxazole
• CAS: 108011-90-1
• 化学式: C₁₅H₉Cl₂NO
• 分子量: 290.149
• InChiKey: MYMIDTCASDIGPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(2,4-dichlorophenyl)-5-phenyloxazole
  参考文献：
  名称：

  Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

  摘要：

  An I-2-promoted sp(3) C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C H bond and the formation of C-N, C-O bonds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.072

文献信息

• 一种恶唑杂环化合物的合成方法
  申请人：常州大学

  公开号：CN110963977A

  公开（公告）日：2020-04-07

  本发明属于有机合成及药物技术领域。具体涉及一种恶唑杂环化合物的合成方法。本发明以芳基醛和三氮唑衍生物作为原料，在三氯甲烷和醋酸铑催化剂存在的条件下，加热发生反应，得到恶唑杂环化合物。使用本发明提出的方法，在加热搅拌条件下，反应3‑12小时，即可以较高产率得到恶唑杂环类衍生物。本发明方法用简单易得的原料，一步法简便高效地合成了恶唑杂环类衍生物，为合成恶唑杂环衍生物提供了一条简单高效，底物普适性广的合成新方法。
• A New Approach to Ring Expansion of Keto Aziridines to 2,5-Diaryloxazoles
  作者：Heshmat Samimi、Somaye Mohammadi

  DOI：10.1055/s-0032-1317925

  日期：——

  Ring expansion of keto aziridines to the corresponding 2,5-diaryl oxazoles in the presence of dicyclohexyl carbodiimide and iodine under refluxing acetonitrile conditions is described. A plausible mechanism is proposed.

  描述了在回流乙腈条件下，在二环己基碳二亚胺和碘的存在下，酮氮丙啶环扩展为相应的 2,5-二芳基恶唑。提出了一种合理的机制。
• Synthesis of 2,5-diaryloxazoles through rhodium-catalyzed annulation of triazoles and aldehydes
  作者：Jian Li、Shang-Rong Zhu、Yue Xu、Xue-Chen Lu、Zheng-Bing Wang、Li Liu、De-feng Xu

  DOI：10.1039/d0ra03966g

  日期：——

  An efficient synthesis of a variety of 2,5-diaryloxazole derivatives via a rhodium-catalyzed annulation of triazoles and aldehydes is achieved. Various oxazole derivatives could be obtained in good to excellent yields. A concise synthesis of antimycobaterial natural products balsoxin and texamine has been achieved using this method.

  通过铑催化的三唑和醛的环化，实现了多种2,5-二芳基恶唑衍生物的有效合成。可以以良好至优异的收率获得各种恶唑衍生物。利用该方法实现了抗真菌天然产物Balsoxin和Texamine的简洁合成。
• N-Bromosuccinimide as a Brominating Agent for the Transformation of N-H (or N-Benzyl) Ketoaziridines into Oxazoles
  作者：Heshmat Samimi、Farkhondeh Dadvar

  DOI：10.1055/s-0034-1380518

  日期：——

  A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.
• C–C Bond Cleavage of Keto-Aziridines; Synthesis of Oxazoles <i>via</i> Regio-Controlled Ring Expansion
  作者：Heshmat Allah Samimi、Soraya Entezami

  DOI：10.3184/174751913x13843364573005

  日期：2013.12

  The ring expansion of keto-aziridines to the corresponding 2,5-diaryloxazoles in the presence of iodine in refluxing dimethyl sulfoxide, is described. A plausible mechanism for the synthesis of 2,5-diaryloxazoles is proposed.