2-ethyl-4-methyl-5-phenyloxazole | 76843-12-4

• 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-ethyl-4-methyl-5-phenyloxazole
• 英文别名: Oxazole, 2-ethyl-4-methyl-5-phenyl-；2-ethyl-4-methyl-5-phenyl-1,3-oxazole
• CAS: 76843-12-4
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: GTYRTACUORCSPA-UHFFFAOYSA-N

物化性质

• 沸点：
  279.6±9.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-ethyl-4-methyl-5-phenyloxazole 、 邻氨基苯甲酸 在 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 1-ethyl-8-phenyl-15-oxatetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaene
  参考文献：
  名称：

  芳烃与恶唑的环加成反应1：各种取代多环烃的便捷合成

  摘要：

  通过芳烃与恶唑的环加成反应合成取代的多环醚和烃。

  DOI：

  10.1016/0040-4039(80)80254-1
• 作为产物：
  描述：

  2,5-Dihydro-2-ethyl-5-hydroxy-4-methyl-5-phenyloxazole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以65%的产率得到2-ethyl-4-methyl-5-phenyloxazole
  参考文献：
  名称：

  Base-Promoted Reactions of .alpha.-Azido Ketones with Aldehydes and Ketones: A Novel Entry to .alpha.-Azido-.beta.-hydroxy Ketones and 2,5-Dihydro-5-hydroxyoxazoles

  摘要：

  The base-promoted reaction of alpha-azido ketones with aldehydes and ketones provides a new and simple route to either alpha-azido-beta-hydroxy ketones, which are valuable 1,2,3-trifunctionalized synthons, or 2,5-dihydro-5-hydroxyoxazoles, which are a little known type of oxazoline. These two products are formed by the electrophilic trapping of two different anions that are produced sequentially during the reaction, The alpha-azido-beta-hydroxy ketones are formed by an aldol reaction between an enolate of the alpha-azidoketone and an aldehyde. The 2,5-dihydro-5-hydroxyoxazoles are formed by electrophilic trapping of an imino anion which is produced by nitrogen loss from the cx-azido ketone enolate.

  DOI：

  10.1021/jo00113a015

文献信息

• One-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles
  作者：Sho Imai、Hiroki Kikui、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2015.06.022

  日期：2015.8

  Alkyl aryl ketones were successfully converted into the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles in good to moderate yields in a one-pot manner, utilizing iodine, Oxone®, and trifluoromethanesulfonic acid in nitriles under transition-metal-free conditions. The present method could be used for the preparation of Oxaprozin from benzyl phenyl ketone and succinonitrile. A possible

  烷基芳基酮成功地转化成相应的2,5-二取代的和2,4,5-三取代的恶唑以优良至适中的产率在一锅方式，利用碘，过硫酸氢钾®，和在腈三氟甲磺酸下过渡金属无条件。本方法可用于由苄基苯基酮和琥珀腈制备氧杂丙嗪。提出了一种可能的反应机理，其中关键的中间体是α-碘烷基烷基芳基酮和α-碘烷基烷基芳基酮。
• Iodoarene-Mediated One-Pot Preparation of 2,4,5-Trisubstituted Oxazoles from Ketones
  作者：Hideo Togo、Yuhta Kawano

  DOI：10.1055/s-2007-1000871

  日期：2008.1

  2-Methyl-5-aryloxazole and 2-ethyl-5-aryloxazole derivatives were smoothly and efficiently obtained in one-pot manner from alkyl aryl ketones with iodoarene, m-chloroperbenzoic acid, and trifluoromethanesulfonic acid in acetonitrile and propionitrile, respectively. In these reactions, iodoarene works as a catalyst.

  2-甲基-5-芳基恶唑和2-乙基-5-芳基恶唑衍生物分别在乙腈和丙腈中以烷基芳基酮与碘芳烃、间氯过苯甲酸和三氟甲磺酸为原料，通过一锅法顺利高效地获得。在这些反应中，碘芳烃起到催化剂的作用。
• Iodoarene-catalyzed one-pot preparation of 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with mCPBA in nitriles
  作者：Yuhta Kawano、Hideo Togo

  DOI：10.1016/j.tet.2009.05.003

  日期：2009.8

  aryliodonium I(III) species reacts with alkyl aryl ketone to form β-keto aryliodonium species. This in turn, reacts with nitrile to form the corresponding oxazole. Iodoarene works as a catalyst. However, one equivalent of iodoarene is required because one equivalent of reactive aryliodonium I(III) species must be formed prior to the reaction with alkyl aryl ketone. Then, by introducing an ionic liquid

  2,4,5-三取代的恶唑类可以在中等的收率由烷基芳基酮，iodoarene的反应容易地制备，中号氯过苯甲酸，并在乙腈，丙腈，丁腈三氟甲磺酸，和异丁腈，分别。在这里，反应性芳基碘鎓I（III）物种是通过碘芳烃与m的反应原位形成的CPBA和三氟甲磺酸与形成的芳基碘鎓I（III）物种与烷基芳基酮反应形成β-酮基芳基碘鎓物种。这又与腈反应形成相应的恶唑。碘芳烃起催化剂的作用。然而，需要一当量的碘芳烃，因为必须在与烷基芳基酮反应之前形成一当量的反应性芳基碘鎓I（III）。然后，通过将离子液体基团引入碘代芳烃中，形成离子液体负载的碘代芳烃，可简化恶唑的分离过程。向反应混合物中加入乙酸乙酯，用NaHCO 3水溶液洗涤反应混合物。，除去乙酸乙酯并用醚萃取残留物可提供中等纯度的恶唑，残留的离子液体负载的碘芳烃可在同一反应中重复使用。
• Iodoarene-mediated one-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with oxone in nitriles
  作者：Yoshihide Ishiwata、Hideo Togo

  DOI：10.1016/j.tet.2009.09.109

  日期：2009.12

  aryliodonium I(III) species reacts with alkyl aryl ketone to generate β-keto iodonium species. Then, β-keto iodonium species reacts with nitrile to produce the corresponding oxazole. In principle, iodoarene works as a catalyst. However, 1 equiv of iodoarene is required because 1 equiv of reactive aryliodonium I(III) species must be formed before the reaction with alkyl aryl ketone.

  烷基芳基酮与过硫酸氢钾反应®和在iodoarene在乙腈，丙腈，丁腈，异丁腈和存在三氟甲磺酸，直接提供相应的2,5-二取代的和分别2,4,5-三取代的恶唑，在温和产量。在此，形成在原位反应芳基碘鎓I（III）物质通过iodoarene与过硫酸氢钾反应®和三氟甲磺酸，形成的芳基碘鎓I（III）与烷基芳基酮反应生成β-酮碘鎓。然后，β-酮碘鎓物质与腈反应生成相应的恶唑。原则上，碘芳烃起催化剂的作用。然而，需要1当量的碘芳烃，因为在与烷基芳基酮反应之前必须形成1当量的反应性芳基碘鎓I（III）物质。
• Coordination‐Controlled Nickel‐Catalyzed Benzylic Allylation of Unactivated Electron‐Deficient Heterocycles
  作者：Pengpeng Zhang、Jin Wang、Zoe R. Robertson、Timothy R. Newhouse

  DOI：10.1002/anie.202200602

  日期：2022.5.23

  A nickel-catalyzed benzylic allylation and benzylation of 14 types of unactivated heterocyclic aromatic compounds is described. The selective deprotonation of benzylic sites is hypothesized to be controlled by the original coordination of a heterocyclic nitrogen to Zn(TMP)2. In addition to the pro-nucleophiles, readily available bromide and chloride electrophiles could be used.

  描述了 14 种未活化的杂环芳族化合物的镍催化苄基烯丙基化和苄基化。假设苄基位点的选择性去质子化受杂环氮与Zn(TMP) 2的原始配位控制。除了前亲核试剂外，还可以使用现成的溴化物和氯化物亲电试剂。