2-(2-chlorophenyl)-5-phenyloxazole | 22397-40-6

• 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-(2-chlorophenyl)-5-phenyloxazole
• 英文别名: 2-(2-chloro-phenyl)-5-phenyl-oxazole；2-(2-Chlor-phenyl)-5-phenyl-oxazol；2-(2-Chlorophenyl)-5-phenyl-1,3-oxazole
• CAS: 22397-40-6
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: IZRRJUCIEXYYBW-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  418.1±47.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)
• 溶解度：
  <0.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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

• 作为产物：
  描述：

  2-氯苯甲酰胺 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 、 对甲苯磺酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 生成 2-(2-chlorophenyl)-5-phenyloxazole
  参考文献：
  名称：

  Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides

  摘要：

  The hypervalent iodine reagent PhI(OTf)(2), generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction.

  DOI：

  10.1055/s-0033-1339491

文献信息

• Convenient One-Pot Synthesis of 2,5-Disubstituted Oxazoles via a Catalytic Oxidative Dehydrogenation of F₃CSO₃H·SiO₂-DDQ/CuCl₂/LiCl
  作者：Shizhen Yuan、Zhen Li、Ling Xu

  DOI：10.1002/jhet.1637

  日期：2013.11

  A facile one‐pot synthesis of 2,5‐disubstituted oxazoles was developed via cyclization of aldoximes and phenylacetylene then dehydrogenation oxidation. 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone was studied for the selective oxidation of oxazolines using Cu2+/Li+ as catalyst and O2 as indirect oxidant. The reaction results showed that this catalyst system can effectively catalyze the oxidation of oxazolines

  通过醛肟和苯乙炔的环化然后脱氢氧化制得了一种简便的一锅合成2,5-二取代的恶唑。以Cu 2+ / Li +为催化剂，O 2为间接氧化剂，研究了2,3-二氯-5,6-二氰基-1,4-苯醌对氧化唑啉的选择性氧化。反应结果表明，该催化剂体系可有效催化恶唑啉氧化为相应的恶唑。因此，通过2,3-二氯-5,6-二氰基-1,4-苯醌/ CuCl 2 / LiCl / O 2的催化氧化，很容易以高收率合成各种多取代的恶唑。
• Copper-catalyzed oxidative cyclization of chalcone and benzylic amine leading to 2,5-diaryl oxazoles via carbon–carbon double bond cleavage
  作者：Dongfang Liu、Jintao Yu、Jiang Cheng

  DOI：10.1016/j.tet.2013.12.077

  日期：2014.2

  oxidative cyclization of chalcone with benzylic amine is achieved, providing 2,5-diaryl oxazoles in moderate to good yields. The procedure employs O2 as a clean oxidant and involves an oxidative cleavage of the CC bond as the key step.

  实现了查尔酮与苄基胺的铜催化氧化环化，以中等至良好的产率提供了2,5-二芳基恶唑。该方法使用O 2作为清洁氧化剂，并且涉及C C键的氧化裂解作为关键步骤。
• 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。
• TBHP/I₂-Mediated Domino Oxidative Cyclization for One-Pot Synthesis of Polysubstituted Oxazoles
  作者：Huanfeng Jiang、Huawen Huang、Hua Cao、Chaorong Qi

  DOI：10.1021/ol1023085

  日期：2010.12.3

  A facile type of one-pot, transition-metal-free domino process was developed for the synthesis of oxazoles. Thus, a variety of polysubstituted oxazoles were easily synthesized via t-BuOOH/I2-mediated domino oxidative cyclization from readily available starting materials under mild conditions.

  开发了一种简便的单罐，无过渡金属的多米诺骨牌工艺，用于合成恶唑。因此，通过t- BuOOH / I 2介导的多米诺氧化环化反应可以容易地在温和条件下从容易获得的起始原料合成多种多取代的恶唑。
• 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。