(2,4-dimethyloxazol-5-yl)(phenyl)methanone | 100063-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4-dimethyloxazol-5-yl)(phenyl)methanone
• 英文别名: (2,4-Dimethyl-1,3-oxazol-5-yl)-phenylmethanone
• CAS: 100063-05-6
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: AXBSQONJMWMZAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,4-dimethyloxazol-5-yl)(phenyl)methanone 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 (2,4-dimethyl-oxazol-5-yl)-phenyl-methanol
  参考文献：
  名称：

  Notes - Synthesis of Heterocyclic Aminoethers Related to Diphenyhydramine

  摘要：

  DOI：

  10.1021/jo01356a601
• 作为产物：
  描述：

  (Z)-N-(4-oxo-4-phenylbut-2-en-2-yl)acetamide 在 三氟化硼乙醚 、 1-氟-3,3-二甲基-1,2-苯并碘氧杂戊环 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以95%的产率得到(2,4-dimethyloxazol-5-yl)(phenyl)methanone
  参考文献：
  名称：

  N-乙酰基烯胺的高价碘介导的合成恶唑和咪唑的反应。

  摘要：

  研究了用于N-乙酰基烯胺分子内环化以及烯胺和腈的分子间环缩合的高价碘试剂。该反应在温和的条件下进行，分别以中等至优异的产率得到恶唑和咪唑。该转化表现出良好的反应性，选择性和官能团耐受性。分子内或分子间反应的选择性取决于N-乙酰基烯胺的结构。

  DOI：

  10.1039/c9ob01895f

文献信息

• Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C−H Halogenation
  作者：Pallaba Ganjan Dalai、Kuntal Palit、Niranjan Panda

  DOI：10.1002/adsc.202101291

  日期：2022.3

  A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C−H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur ylide, which undergoes pyrolytic elimination of ethylene by affording halonium ions. These ions were accumulated and stabilized by DMSO through coordination

  报道了一种通过 1,2-二卤代乙烷 (hal=Br, I) 和二甲基亚砜 (DMSO) 的反应生成卤素阳离子池的方法，用于芳烃和杂芳烃的 C-H 卤化。DMSO 和 1,2-二卤代乙烷的初始反应生成硫叶立德，其通过提供卤离子来热解消除乙烯。DMSO 通过配位形成卤化反应的卤离子池，从而积累和稳定这些离子。该方案在室温下对芳烃的亲电单卤化具有选择性；但是，通过提高反应温度会形成多卤代产物。杂芳烃和一些常用药物的后期卤化表明该协议在药物化学中的合成效用。与经典方法不同，
• I₂-Catalyzed C–O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases
  作者：Wen-Chao Gao、Fei Hu、Yu-Ming Huo、Hong-Hong Chang、Xing Li、Wen-Long Wei

  DOI：10.1021/acs.orglett.5b01933

  日期：2015.8.7

  A general method for the synthesis of oxazolines and oxazoles was developed through I-2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively produced from beta-acylamino ketones.
• Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization
  作者：Yunhui Zheng、Xuming Li、Chengfeng Ren、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/jo302073e

  日期：2012.11.16

  A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.
• Synthesis of 2-(Trifluoromethyl)oxazoles from β-Monosubstituted Enamines via PhI(OCOCF₃)₂-Mediated Trifluoroacetoxylation and Cyclization
  作者：Feifei Zhao、Xin Liu、Rui Qi、Daisy Zhang-Negrerie、Jianhui Huang、Yunfei Du、Kang Zhao

  DOI：10.1021/jo202070h

  日期：2011.12.16

  Treatment of beta-monosubstituted enamines with phenyliodine bis(trifluoroacetate) (PIFA) was found to give a variety of 4,5-disubstituted 2-(trifluoromethyl)oxazoles. This approach allows the incorporation of the trifluoromethyl moiety in PIFA into the final products, which presumably takes place via the oxidative beta-trifluoroacetoxylation of the enamine substrates followed by subsequent intramolecular cyclization.
• A rapid access to substituted oxazoles via PIFA-mediated oxidative cyclization of enamides
  作者：Midori Kamiya、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1016/j.tet.2017.01.027

  日期：2017.3

  A facile and rapid access to multi-substituted oxazoles has been achieved under mild reaction conditions in a short reaction time. Reaction of enamides 1 with [bis(trifluoroacetoxy)iodo]benzene (PIFA) in trifluoroethanol (TFE) at room temperature for 15 min afforded the desired oxazoles 2 in moderate to excellent yields (58-98%). A wide range of functional group tolerance has been observed for these transformations. (C) 2017 Elsevier Ltd. All rights reserved.