5-(4-ethoxyphenyl)-2-phenyloxazole | 1373758-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-ethoxyphenyl)-2-phenyloxazole
• 英文别名: 5-(4-Ethoxyphenyl)-2-phenyl-1,3-oxazole
• CAS: 1373758-48-5
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: IQDHAQHIDPBSAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙氧基苯乙酮 在 碘 作用下， 以 二甲基亚砜 为溶剂， 生成 5-(4-ethoxyphenyl)-2-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

• Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines
  作者：Zejun Xu、Chun Zhang、Ning Jiao

  DOI：10.1002/anie.201206382

  日期：2012.11.5

  A fragment‐assembling strategy is used to form oxazoles from aryl acetaldehydes, amines, and molecular oxygen under mild conditions (see scheme). The transformation is highly efficient with the removal of six hydrogen atoms, including the cleavage of four C(sp3)H bonds.

  片段组装策略用于在温和条件下由芳基乙醛，胺和分子氧形成恶唑（请参阅方案）。通过去除六个氢原子，包括四个C（sp 3）H键的裂解，该转化过程非常高效。
• Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence
  作者：Anxin Wu、Jungang Wang、Yan Cheng、Jiachen Xiang

  DOI：10.1055/s-0037-1612087

  日期：2019.4

  5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO3)2•3H2O and iodine. This reaction ­process involves the I2/Cu(NO3)2•3H2O-assisted transformation of ­arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.

  在 Cu(NO3)2•3H2O 和碘的存在下，从容易获得的芳基乙炔和 α-氨基酸合成 2,5-二取代恶唑的新策略已经开发出来。该反应过程包括 I2/Cu(NO3)2•3H2O 辅助芳基乙炔转化为 α-碘苯乙酮、Kornblum 氧化为苯乙二醛、缩合为亚胺、脱羧/环化/氧化反应序列以接近 2,5-二取代恶唑。
• Synthesis of 2,5-Disubstituted Oxazoles and Oxazolines Catalyzed by Ruthenium(II) Porphyrin and Simple Copper Salts
  作者：Chuan Long Zhong、Bo Yang Tang、Ping Yin、Yue Chen、Ling He

  DOI：10.1021/jo202663n

  日期：2012.5.4

  A novel and moderate synthesis of 2,5-disubstituted oxazoles and oxazolines involving ruthenium(II) porphyrin copper chloride catalyzed cyclization was developed. These reactions using readily available benzene carboxylic acids and phenylethenes or phenylacetylenes are performed under mild conditions. The reactions proceed in series, giving rise to the formation of an intermolecular C-N bond and an intramolecular C-O bond, which yield oxazole or oxazoline derivatives simultaneously.
• PURINE DIONES AS WNT PATHWAY MODULATORS
  申请人：Agency for Science, Technology and Research

  公开号：EP2999699A1

  公开（公告）日：2016-03-30
• Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles
  作者：Qing-He Gao、Zhuan Fei、Yan-Ping Zhu、Mi Lian、Feng-Cheng Jia、Mei-Cai Liu、Neng-Fang She、An-Xin Wu

  DOI：10.1016/j.tet.2012.10.072

  日期：2013.1

  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.