噁唑,2-(4-溴苯基)-5-苯基- | 14492-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 噁唑,2-(4-溴苯基)-5-苯基-
• 英文名称: 2-(4-bromophenyl)-5-phenyloxazole
• 英文别名: 2-(4-Bromophenyl)-5-phenyl-1,3-oxazole
• CAS: 14492-02-5
• 化学式: C₁₅H₁₀BrNO
• 分子量: 300.154
• InChiKey: KQKZBILGPDPYLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-溴代联苯 、 噁唑,2-(4-溴苯基)-5-苯基- 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.17h， 以72%的产率得到2-terphenyl-4-yl-5-phenyloxazole
  参考文献：
  名称：

  Javelin-, Hockey Stick-, and Boomerang-Shaped Liquid Crystals. Structural Variations on p-Quinquephenyl

  摘要：

  The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases), However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.

  DOI：

  10.1021/jp010869j
• 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96%的产率得到噁唑,2-(4-溴苯基)-5-苯基-
  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

• A Domino Copper-Catalyzed C-N and C-O Cross-Coupling for the Conversion­ of Primary Amides into Oxazoles
  作者：Frank Glorius、Kerstin Schuh (née Müller)

  DOI：10.1055/s-2007-983782

  日期：2007.7

  A variety of oxazoles can efficiently be prepared, in a single step and in good yield, from primary amides and 1,2-dihaloalkenes using copper-catalysis. This new method allows the re-gioselective formation of a range of substituted oxazoles. The required 1,2-dihaloalkenes can prepared by simple treatment of alkynes with elemental bromine or iodine.

  使用铜催化，伯酰胺和 1,2-二卤代烯烃可在一个步骤中以良好的收率有效地制备各种恶唑。这种新方法允许区域选择性地形成一系列取代的恶唑。所需的 1,2-二卤代烯烃可以通过用元素溴或碘对炔烃进行简单处理来制备。
• Water-Binding Solid Scintillators: Synthesis, Emission Properties, and Tests in3H and14C Counting
  作者：Hans-Joachim Meyer、Thomas Wolff

  DOI：10.1002/1521-3765(20000804)6:15<2809::aid-chem2809>3.0.co;2-m

  日期：2000.8.4

  Spectral and time-resolved fluorescence properties as well as relative fluorescence quantum yields of carbodiimide derivatives of 2.5-diphenyloxazole (PPO) (prepared by H2S elimination from the corresponding thioureas), of some intermediates in the preparation, and of several other PPO derivatives were investigated in solution and in the solid state to test their suitability as solid scintillators

  研究了2.5-二苯基恶唑（PPO）（通过从相应的硫脲中脱除H2S制备）的碳二亚胺衍生物，制备中的某些中间体以及其他几种PPO衍生物的光谱和时间分辨荧光性质以及相对荧光量子产率在溶液中和固态下测试其作为固态闪烁体的适用性。碳二亚胺在酸性条件下与水缓慢反应，生成脲。在3H和14C计数中，将这些系统与其他PPO衍生物与硫酸钠作为干燥剂的固体混合物进行了比较，将其作为化学结合水的固体闪烁体。化学和吸收性水结合闪烁体都证明能够计算3H和14C衰减，
• I2/TBHP-mediated domino process: a convenient route to 1,3-oxazole derivatives
  作者：Cheng-Tao Feng、Ming Zhao、Shi-Tang Ma、Xia Qin

  DOI：10.1007/s11164-012-0885-2

  日期：2013.10

  (tert-butyl hydroperoxide)/I2-mediated domino strategy. The reaction proceeds in series, giving rise to the formation of an intermolecular C–N bond and an intramolecular C–O bond, which yield oxazole derivatives simultaneously. The reaction gave the desired products from readily available substrates under mild conditions.

  通过TBHP（氢过氧化叔丁基）/ I 2介导的多米诺骨牌战略，开发了一种实用且简单的2,5-二取代的恶唑合成方法。反应是连续进行的，形成了分子间的C–N键和分子内的C–O键，这些键同时生成恶唑衍生物。该反应在温和条件下从容易获得的底物中得到所需产物。
• Metal-free iodine(<scp>iii</scp>)-promoted synthesis of 2,5-diaryloxazoles
  作者：Xueying Yang、Xin Guo、Mingda Qin、Xinglong Yuan、Huanwang Jing、Baohua Chen

  DOI：10.1039/c8ob00401c

  日期：——

  A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and

  描述了在室温下由廉价且容易获得的取代的查耳酮，（二乙酰氧基碘）苯（PIDA）和乙酸铵（NH 4 OAc）实现2,5-二取代的恶唑的非金属催化的氧化环化。该反应在温和条件下以不需要的配体和额外的碱即可以良好的产率和优异的产率形成各种2,5-二芳基恶唑，具有广泛的底物范围。
• Iodine catalysed intramolecular C(sp³)–H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides
  作者：Supravat Samanta、Ramachandra Reddy Donthiri、Milan Dinda、Subbarayappa Adimurthy

  DOI：10.1039/c5ra13441b

  日期：——

  Iodine catalyzed synthesis of 2,5-substituted oxazoles from N-arylethylamides through intramolecular C(sp³)–H functionalization under metal-free conditions is described.

  碘催化合成2,5-取代噁唑，通过金属无催化条件下的分子内C(sp3)–H官能化，从N-芳基乙酰胺中进行描述。