(2,5-diphenyloxazol-4-yl)(phenyl)methanone | 57742-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,5-diphenyloxazol-4-yl)(phenyl)methanone
• 英文别名: (2,5-Diphenyl-1,3-oxazol-4-yl)(phenyl)methanone；(2,5-diphenyl-1,3-oxazol-4-yl)-phenylmethanone
• CAS: 57742-56-0
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: BXPMHLLENMGMEE-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  550.0±52.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  甲基碘化镁 、 (2,5-diphenyloxazol-4-yl)(phenyl)methanone 以 乙醚 为溶剂， 生成 1-(2,5-diphenyl-oxazol-4-yl)-1-phenyl-ethanol
  参考文献：
  名称：

  Photochemical transformations of small ring heterocyclic compounds. 70. Thermal and photochemical valence isomerizations of 4-carbonyl-substituted isoxazoles

  摘要：

  DOI：

  10.1021/ja00855a033
• 作为产物：
  描述：

  2,5-二苯基恶唑 在 2,2,6,6-四甲基哌啶 、 jones reagent 、 仲丁基锂 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 (2,5-diphenyloxazol-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Substituted oxazoles: syntheses via lithio intermediates

  摘要：

  Reactions of 2-alpha-, 2-, 4-, and 5-lithiooxazoles are used to prepare various substituted derivatives. Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldehyde is described, and a rationale for this behavior is offered. Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with n-butyllithium. Deprotonation of the ortho position of the 2-phenyl group and addition of n-butyl to the 2-position of the oxazole compete with the desired 4-lithiation. The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-25-diphenyloxazole. This intermediate has been converted to the 4-bromo, -methyl, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivatives. Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position. Deprotonation of 2-alkyloxazoles occurs at the alpha-carbon in preference to ring sites. Further reaction of an alpha-phenyl-2-oxazolemethanol methoxymethyl ether with base and acetyl chloride leads to an acyloin derivative. Chromic acid oxidation is used to prepare both 2- and 4-benzoyloxazoles. The formation of a 2-ethoxyoxazole from the 2-oxazolone vis Meerwein salt chemistry is described.

  DOI：

  10.1021/jo00009a025

文献信息

• Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles
  作者：Akio Saito、Nao Hyodo、Yuji Hanzawa

  DOI：10.3390/molecules170911046

  日期：——

  trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf2NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions.

  在三氟甲磺酸 (TfOH) 或双（三氟甲磺酰基）酰亚胺 (Tf2NH) 存在下，碘代苯 (PhI=O) 有效地促进了二羰基化合物以及单羰基化合物与腈的反应，生成 2,4-二取代和 2 ,4,5-三取代恶唑在温和条件下一步完成。
• A Highly Efficient Heterogeneous Copper-Catalyzed Oxidative Cyclization of Benzylamines and 1,3-Dicarbonyl Compounds To Give Trisubstituted Oxazoles
  作者：Li Wei、Shengyong You、Yuxin Tuo、Mingzhong Cai

  DOI：10.1055/s-0037-1610710

  日期：2019.8

  yields. This heterogeneous copper catalyst can be facilely prepared via a simple two-step procedure from readily available and inexpensive reagents and exhibits a slightly higher activity than Cu(OAc)2. MCM-41-2N-Cu(OAc)2 is also easy to recover and can be recycled up to eight times with almost consistent activity. The reaction is the first example of heterogeneous copper-catalyzed intermolecular cyclization

  抽象的 通过使用3-（2-氨基乙基氨基）丙基官能化的MCM-41固定铜（II）配合物[MCM-41-2N-Cu]，实现苄胺和1,3-二羰基化合物之间铜的多相铜级联氧化环化反应（OAc）2 ]作为催化剂，t- BuOOH（TBHP）作为氧化剂，以碘为添加剂，在温和的条件下，可产生多种2,4,5-三取代的恶唑，收率大多良好至极佳。可以通过简单的两步程序轻松地从容易获得的廉价试剂制备这种多相铜催化剂，并且其活性比Cu（OAc）2略高。MCM-41-2N-Cu（OAc）2回收也很容易，可以回收八次，几乎保持一致的活性。该反应是用于构建多取代的恶唑的非均相铜催化的分子间环化的第一个实例。 通过使用3-（2-氨基乙基氨基）丙基官能化的MCM-41固定铜（II）配合物[MCM-41-2N-Cu]，实现苄胺和1,3-二羰基化合物之间铜的多相铜级联氧化环化反应（OAc）2 ]作为催化剂，t- BuOOH（T
• Convenient Route to Trisubstituted Oxazoles via a Copper-Catalysed Tandem Oxidative Cyclisation by Oxygen Oxidation
  作者：Chengqun Chen、Wenfu Chen、Qianhong Bao

  DOI：10.3184/174751915x14192609116136

  日期：2015.1

  cyclisation has been developed for the synthesis of trisubstituted oxazoles, which is thought to proceed through cascade formation of C-N and C-O bonds by oxygen oxidation. The desired products can be obtained from readily available starting materials while avoiding hazardous materials. Therefore, a green synthetic method for the preparation of oxazoles has been found.

  一种新型的铜催化氧化环化反应已被开发用于合成三取代恶唑，据认为该反应是通过氧氧化级联形成 CN 和 CO 键来进行的。所需的产品可以从容易获得的起始材料中获得，同时避免使用有害材料。因此，发现了一种制备恶唑的绿色合成方法。
• Metal-free, organocatalytic cascade formation of C–N and C–O bonds through dual sp³C–H activation: oxidative synthesis of oxazole derivatives
  作者：Jin Xie、Honglai Jiang、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c2cc15813b

  日期：——

  An organocatalytic cascade reaction that involves the formation of C-N, C-O and C=N bonds in one process via dual sp(3) C-H activation has been developed. This protocol affords a facile metal-free methodology for the synthesis of oxazole derivatives in air under mild conditions.

  已经开发了一种有机催化级联反应，该过程涉及通过双sp（3）CH活化在一个过程中形成CN，CO和C = N键。该方案为在温和条件下在空气中合成恶唑衍生物提供了一种简便的不含金属的方法。
• 10.1002/cjoc.202400481
  作者：Gao, Shuo、Hao, Wentao、Ji, Yuqi、Li, Xiulin、Zhang, Chunyan、Zhang, Guoying

  DOI：10.1002/cjoc.202400481

  日期：——

  practical Co-catalyzed cascade dehydrogenative Claisen condensation of secondary alcohols with esters, facilitating the synthesis of a wide range of 3-hydroxy-prop-2-en-1-ones. We introduce a catalytic system based on novel and scalable indazole NNP-ligands coordinated to cobalt for efficient dehydrogenations of secondary alcohols, and propose a plausible reaction mechanism supported by control experiments

  催化脱氢具有卓越的原子经济性和化学选择性，为将多种环保醇转化为关键分子提供了一种非常理想但具有挑战性的方法。此外，利用基于地球上发现的丰富元素的催化剂进行醇脱氢以生产丙烯酸酮，作为合成众多制药应用关键构件的通用策略，具有重要的前景。本研究描述了仲醇与酯的实用共催化级联脱氢 Claisen 缩合反应，促进了广泛的 3-羟基-丙-2-烯-1-酮的合成。我们引入了一种基于新型且可扩展的吲唑 NNP 配体的催化系统，该配体与钴配位，用于仲醇的高效脱氢，并提出了一种由对照实验和标记研究支持的合理反应机制。值得注意的是，它允许在一个罐中简化多种药物的合成。