3,4,5-三苯基-2(3H)-恶唑酮 | 6652-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3,4,5-三苯基-2(3H)-恶唑酮
• 英文名称: 2-Oxo-3,4,5-triphenyl-2,3-dihydro-oxazol
• 英文别名: 3,4,5-triphenyl-4-oxazolin-2-one；3,4,5-Triphenyl-3H-oxazol-2-one；2,4-Diphenyl-2(3H)-oxazolone；3,4,5-triphenyl-3H-oxazol-2-one；triphenyl-3H-oxazol-2-one；Triphenyl-3H-oxazol-2-on；2(3H)-Oxazolone, 3,4,5-triphenyl-；3,4,5-triphenyl-1,3-oxazol-2-one
• CAS: 6652-42-2
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: OOIRRIVSRGZVHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5-三苯基-2(3H)-恶唑酮 在 tetraphosphorus decasulfide 、 xylene 作用下， 生成 3,4,5-triphenyl-4-oxazoline-2-thione
  参考文献：
  名称：

  Gompper, Chemische Berichte, 1956, vol. 89, p. 1762,1767

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-diphenyl-2-(phenylamino)ethanone 在 氢氧化钾 、 碳酸氢钠 作用下， 生成 3,4,5-三苯基-2(3H)-恶唑酮
  参考文献：
  名称：

  McCombie; Parkes, Journal of the Chemical Society, 1912, vol. 101, p. 1997

  摘要：

  DOI：

文献信息

• Cyclizations of Dianions from 2-Imino-1,2-diphenylethanone to Oxazolines, Oxazocines, and Oxazonines
  作者：Kailash Nath Mehrotra、Indra Sen Singh、Jalpana Roy

  DOI：10.1246/bcsj.58.2399

  日期：1985.8

  2-diphenylethanone with sodium in ether and subsequent addition of carbon disulfide or ethyl chloroformate resulted in the formation of 3,4,5-trisubstituted 4-oxazoline-2-thiones and 2-ones, respectively. 1,4-Oxazonines and 1,4-oxazocines were also synthesised from the reaction of 2-imino-1,2-diphenylethanone with sodium in THF followed by addition of dihaloalkanes.

  2-亚氨基-1,2-二苯基乙酮与钠在乙醚中反应，随后加入二硫化碳或氯甲酸乙酯，分别生成 3,4,5-三取代的 4-恶唑啉-2-硫酮和 2-酮. 1,4-恶唑啉和 1,4-恶唑嗪也由 2-亚氨基-1,2-二苯基乙酮与钠在 THF 中的反应合成，然后加入二卤代烷烃。
• Cyclization Reaction of Bis(tributylstannylated) α-Ketols with Heterocumulenes. Preparation of<i>O</i>,<i>O</i>-Vinylene Imino- and Thiocarbonates
  作者：Shizuyoshi Sakai、Masashi Murata、Nobuto Wada、Tatsuo Fujinami

  DOI：10.1246/bcsj.56.1873

  日期：1983.6

  Aromatic α-ketols reacted with diethylaminotributylstannane at 60 °C to afford a mixture of (Z)- and (E)-1,2-bis(tributylstannyloxy)-1,2-diarylethenes, which were allowed to react with organic isothiocyanates and carbon disulfide to give substituted O,O-vinylene imino- and thiocarbonates, respectively. Aliphatic α-ketol, 3-hydroxy-2-butanone, was treated by the aminostannane, followed by the reaction with carbon disulfide to form (E)-1,2-bis(tributylstannylthio)-2-butene.

  芳香族α-酮醇在60°C下与二乙氨基三丁基锡反应，生成(Z)-和(E)-1,2-双(三丁基锡氧基)-1,2-二芳基乙烯的混合物，这些混合物进一步与有机异硫氰酸酯和二硫化碳反应，分别得到取代的O,O-乙烯基亚胺碳酸酯和硫代碳酸酯。脂肪族α-酮醇，3-羟基-2-丁酮，经氨基锡化合物处理后，再与二硫化碳反应，形成(E)-1,2-双(三丁基锡硫基)-2-丁烯。
• A Single-Step Synthesis of 4-Oxazolin-2-ones and Their Use in the Construction of Polycyclic Structures Bearing Quaternary Stereocenters
  作者：Blanca M. Santoyo、Carlos González-Romero、Omar Merino、Rafael Martínez-Palou、Aydeé Fuentes-Benites、Hugo A. Jiménez-Vázquez、Francisco Delgado、Joaquín Tamariz

  DOI：10.1002/ejoc.200900114

  日期：2009.5

  for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of α-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity

  报道了一种通过 α-酮醇和异氰酸酯的一锅 MW 促进缩合合成 4-恶唑啉-2-酮的新方法。还描述了使用相同起始材料的替代热方法。这些环状烯酰胺是有效的亲核试剂，可与迈克尔受体和异戊二烯基溴反应，得到各种带有一个或两个四元立体中心的多环结构。产物的选择性取决于反应条件和所用的亲电试剂。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Palladium-Catalyzed Intramolecular Cyclization of Ynamides: Synthesis of 4-Halo-oxazolones
  作者：Hai Huang、Guangke He、Guohao Zhu、Xiaolin Zhu、Shineng Qiu、Hongjun Zhu

  DOI：10.1021/acs.joc.5b00071

  日期：2015.4.3

  A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the

  开发了一种温和有效的方法，该方法涉及Pd（PPh 3）4催化的N-炔基烷氧基氨基甲酸酯与CuCl 2或CuBr 2的分子内环化反应，用于合成4-卤代恶唑酮。该反应显示出良好的功能耐受性，为4-卤代恶唑酮提供了新的，有效的和快速的合成方法。所得的4-卤代恶唑酮可通过Pd催化的交叉偶联反应作为3,4,5-三取代的恶唑酮的潜在潜在前体。
• THE PHOTOCHEMICAL REACTION OF 3,4,5-TRIPHENYL-4-OXAZOLIN-2-ONE
  作者：Otohiko Tsuge、Koji Oe、Yasuo Ueyama

  DOI：10.1246/cl.1976.425

  日期：1976.5.5

  Irradiation of 3,4,5-triphenyl-4-oxazolin-2-one (1) in benzene, under nitrogen, with or without iodine gave benzanilide and phenanthroxazolinone 2. However, in the presence of oxygen 1 was photochemically converted to benzanilide, benzoic acid, and benzamidobenzophenones. This photooxygenation is interpreted by the pathway proceeding via an initial attack of singlet oxygen to 1 forming a dioxetane, followed by ring cleavage to yield N,N-dibenzoylaniline (6) which gives final products.

  在氮气氛围下，使用或不使用碘对3,4,5-三苯基-4-噁唑啉-2-酮（1）进行照射，得到了苯腈和苯并呋喃噁唑啉酮2。然而，在氧气存在的情况下，1经过光化学反应转化为苯腈、苯甲酸和苯基二苯基酮。这种光氧化反应可以解释为：首先单重态氧对1进行攻击，形成二氧烯，然后经过环裂解生成N,N-二苯甲酰基苯胺（6），最终产物由此产生。