2-phenyl-5-(thiophen-3-yl)oxazole | 1261297-49-7

• 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-phenyl-5-(thiophen-3-yl)oxazole
• 英文别名: 2-Phenyl-5-thiophen-3-yl-1,3-oxazole
• CAS: 1261297-49-7
• 化学式: C₁₃H₉NOS
• 分子量: 227.287
• InChiKey: JRMSBBPWSQMOQC-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±34.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 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：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-N-(2-(thiophen-3-yl)vinyl)benzamide 在 dipotassium peroxodisulfate 、 烟酸乙酯 、 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以59%的产率得到2-phenyl-5-(thiophen-3-yl)oxazole
  参考文献：
  名称：

  Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

  摘要：

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

  DOI：

  10.1021/jo301332s

文献信息

• Synthesis of 2,5-disubstituted oxazoles <i>via</i> cobalt(<scp>iii</scp>)-catalyzed cross-coupling of <i>N</i>-pivaloyloxyamides and alkynes
  作者：Xiaolong Yu、Kehao Chen、Qi Wang、Wenjing Zhang、Jin Zhu

  DOI：10.1039/c7cc08611c

  日期：——

  An efficient synthesis of 2,5-disubstituted oxazoles via Co(III) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated

  本文描述了通过Co（III）催化的2，5-二取代的恶唑的有效合成。N-新戊酰氧基酰胺和炔烃的[3 + 2]环加成反应可在温和的条件下完成。该反应通过内部氧化途径进行，并且具有非常广泛的底物范围。通过该方案已证明了天然产品（如特克明和巴色辛）的一步合成。
• Reaction of Alkynes and Azides: Not Triazoles Through Copper-Acetylides but Oxazoles Through Copper-Nitrene Intermediates
  作者：Estela Haldón、Maria Besora、Israel Cano、Xacobe C. Cambeiro、Miquel A. Pericàs、Feliu Maseras、M. Carmen Nicasio、Pedro J. Pérez

  DOI：10.1002/chem.201303737

  日期：2014.3.17

  Well‐defined copper(I) complexes of composition [Tpm*,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5‐dimethyl‐4‐bromo‐pyrazolyl)methane) or [Tpa*Cu]PF6 (Tpa*=tris(3,5‐dimethyl‐pyrazolylmethyl)amine) catalyze the formation of 2,5‐disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily

  [ Tpm * ，Br Cu（NCMe）] BF 4（Tpm * ，Br = tris（3,5-二甲基-4-溴代吡唑基）甲烷）或[Tpa * Cu]的定义明确的铜（I）配合物PF 6（TPa *= tris（3,5-二甲基-吡唑烷基甲基）胺直接催化羰基叠氮化物和末端炔烃形成2,5-二取代的恶唑。该过程代表了一种从容易获得的起始原料合成这种有价值的杂环的新颖方法，仅导致2,5-异构体，证明了其完全的区域选择性转化。通过实验证据和计算研究，提出了基于铜-酰基氮烯物种初始形成的反应机理的建议，与引发铜催化的炔烃和叠氮化物环加成反应（CuAAC）的众所周知的机理相反通过形成铜-乙炔化物络合物。
• 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( )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。
• Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes
  作者：Israel Cano、Eleuterio Álvarez、M. Carmen Nicasio、Pedro J. Pérez

  DOI：10.1021/ja109732s

  日期：2011.1.19

  The reaction of 1-alkynes with acyl azides in the presence of [Tpm*Cu-,Cu-Br(NCMe)]BF4 [Tpm*(,Br) = tris(3,5-dimethyl-4-bromopyrazolyl)methane] as the catalyst provides 2,5-oxazoles in moderate to high yields. This is a novel transformation of the CuAAC type that constitutes a significant variation of the commonly observed [3 + 2] cycloaddition reaction to yield 1,2,3-triazoles.