2-(2-甲基苯基)-5-苯基-1,3-噁唑 | 17064-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(2-甲基苯基)-5-苯基-1,3-噁唑
• 英文名称: 2-(2-methylphenyl)-5-phenyl-1,3-oxazole
• 英文别名: 2-(2-methylphenyl)-5-phenyloxazole；5-phenyl-2-(o-tolyl)oxazole；2-(2-methylphenyl)oxazole；5-phenyl-2-o-tolyloxazole；5-phenyl-2-o-tolyl-oxazole；5-Phenyl-2-o-tolyl-oxazol
• CAS: 17064-20-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: WUKKEHCYQNLZRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以97%的产率得到2-(2-甲基苯基)-5-苯基-1,3-噁唑
  参考文献：
  名称：

  N-酰基-异恶唑5（2 H）-ones的光氧化还原催化发散转化为恶唑和1,3-Oxazin-6-ones

  摘要：

  已经公开了使用可见光光氧化还原催化的N-酰基-异恶唑-5-酮的断裂。利用了催化剂控制的发散机理，即氧化和还原淬灭催化循环。在温和条件下，可从相同的异恶唑-5-酮骨架选择性地获得各种恶唑和1,3-恶嗪6-1酮。

  DOI：

  10.1021/acs.orglett.9b00903

文献信息

• Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis
  作者：Tanmay Chatterjee、Ji Young Cho、Eun Jin Cho

  DOI：10.1021/acs.joc.6b00989

  日期：2016.8.19

  A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also

  已经开发了一种简单而实用的合成取代的恶唑的方法，该方法使用易得的α-溴代酮和苄胺，在室温下通过可见光光催化进行合成。该方法需要1摩尔％的具有K 3 PO 4和CCl 3 Br的[Ru（bpy）3 ] Cl 2光催化剂，可有效地获得各种有价值的恶唑化合物。我们的协议的合成效用也通过制备天然产物texaline得到了证明。
• 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。
• 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。
• Practical oxazole synthesis mediated by iodine from α-bromoketones and benzylamine derivatives
  作者：Wen-Chao Gao、Ruo-Lin Wang、Chi Zhang

  DOI：10.1039/c3ob41566j

  日期：——

  system of I2/K2CO3 could efficiently promote the oxazole synthesis from α-bromoketones and benzylamine derivatives in DMF. This method was not only suitable for 2,5-diaryl oxazole synthesis but also for 2,4,5-trisubstituted oxazole and 5-alkyl/alkenyl oxazole synthesis. Furthermore, this method was successfully applied to a one-step synthesis of a natural product halfordinol in 62% yield.

  I 2 / K 2 CO 3试剂体系可有效促进DMF中α-溴代酮和苄胺衍生物的恶唑合成。该方法不仅适用于2，5-二芳基恶唑的合成，而且适用于2，4，5-三取代的恶唑和5-烷基/烯基恶唑的合成。此外，该方法已成功地以62％的收率成功地一步合成了天然产物Halfordinol。
• Palladium-Catalyzed Cross Coupling Reactions of Oxazol-2-ylzinc Chloride Derivatives
  作者：Benjamin A. Anderson、Nancy K. Harn

  DOI：10.1055/s-1996-4274

  日期：1996.5

  Oxazol-2-ylzinc chloride derivatives were prepared by transmetallation of the corresponding oxazol-2-yllithium species. The palladium-catalyzed cross coupling reactions of the resulting organometallic reagents were investigated with aryl halides and organotriflates.

  通过相应的oxazol-2-yllithium物种的金属转移反应制备了oxazol-2-yl锌氯化物衍生物。研究了所得有机金属试剂在钯催化下的交叉偶联反应，涉及芳基卤化物和有机三氟甲磺酸盐。