5-氯-2-(4-甲氧基苯基)-1,3-苯并恶唑 | 891-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氯-2-(4-甲氧基苯基)-1,3-苯并恶唑
• 英文名称: 5-chloro-2-(4-methoxyphenyl)benzo[d]oxazole
• 英文别名: 5-Chloro-2-(4-methoxyphenyl)-1,3-benzoxazole
• CAS: 891-15-6
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: BPYMXOZKPMEEDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.07
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-(4-chlorophenyl)hydroxylamine 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 生成 5-氯-2-(4-甲氧基苯基)-1,3-苯并恶唑
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632

文献信息

• Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes
  作者：Phuong Hoang Tran、Anh-Hung Thi Hang

  DOI：10.1039/c8ra01094c

  日期：——

  A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.

  开发了一种由深共熔溶剂催化苯并恶唑与芳香醛芳基化的新型有效方法。该反应在各种底物上顺利进行，在很短的反应时间内以高产率得到所需的产物。低共熔溶剂很容易回收和重复使用，而不会显着损失催化活性。
• p -Toluenesulfonic acid-catalyzed metal-free formal [4 + 1] heteroannulation via N H/O H/S H functionalization: One-pot access to 2-aryl/hetaryl/alkyl benzazole derivatives
  作者：Abhijeet Srivastava、Gaurav Shukla、Maya Shankar Singh

  DOI：10.1016/j.tet.2016.12.073

  日期：2017.2

  concise and direct one-pot [4 + 1] synthetic strategy for the construction of 2-substituted benzazoles such as benzoxazoles and benzothiazoles has been disclosed in high yields (80–98%) by cascade coupling reaction of 2-amino(thio)phenols with β-oxodithioesters. The current approach enables NH/OH/SH functionalization in one-pot under solventless condition leading to diverse benzazoles without use of any

  通过2-氨基（硫代）的级联偶联反应，已公开了一种高产率（80-98％）的简洁，直接的一锅[4 +1]合成策略，用于构建2-取代的苯并唑，如苯并恶唑和苯并噻唑酚与β-氧二硫代酯。目前的方法可以在无溶剂条件下在一锅中实现N H / O H / S H官能化，从而无需使用任何外部金属即可产生多种苯并恶唑。各种各样的2-氨基（硫代）酚和β-氧二硫代酯均具有出色的官能团耐受性，可用于该转化。此外，我们通过证明其与DNA拓扑异构酶II抑制剂的多样化多样化的相容性，抢占了这一新策略的广泛含义。
• Palladium-Catalyzed Carbonylative CH Activation of Heteroarenes
  作者：Xiao-Feng Wu、Pazhamalai Anbarasan、Helfried Neumann、Matthias Beller

  DOI：10.1002/anie.201003895

  日期：——

  Not only carbonylation: The first carbonylative cross‐coupling reactions towards ketones using CH activation have been developed. Various heteroarenes, such as oxazoles, thiazoles, and imidazoles were used as coupling partners in this methodology. DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene, dppp=1,3‐bisdiphenylphosphinopropane, DMF=N,N‐dimethylformamide.

  不仅羰基化：已经开发出使用CH活化作用与酮进行的首个羰基交叉偶联反应。在该方法中，各种杂芳基化合物，例如恶唑，噻唑和咪唑被用作偶联伴侣。DBU ＝ 1，8-二氮杂双环[5.4.0]十一月-7-烯，dppp ＝ 1，3-双二苯基膦基丙烷，DMF ＝N，N-二甲基甲酰胺。
• Iron(III) Chloride Mediated <i>para</i> ‐Selective C‐H Functionalization: Access to C5‐Chloro and C5,C7‐Dichloro/Dianisyl Substituted 2‐Arylbenzoxazoles
  作者：Kanchanbala Sahoo、Niranjan Panda

  DOI：10.1002/adsc.202101359

  日期：2022.3

  Iron(III) chloride mediated para-selective C−H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole by ferric chloride was explored to achieve the remotely anisylated benzoxazoles.

  开发了氯化铁 (III) 介导的对位选择性 C-H 氯化和随后的 2-氨基苯酚环化以合成 C5-和 C5、C7-氯化苯并恶唑。此外，还探索了三氯化铁对氨基苯酚与苯甲醚的氧化交叉脱氢偶联，以实现远程苯甲酰化苯并恶唑。
• Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis
  作者：Junbiao Chang、Kang Zhao、Shifeng Pan

  DOI：10.1016/s0040-4039(01)02302-4

  日期：2002.2

  The Schiff base derived from the condensation of o-aminophenol with benzaldehydes was induced to undergo oxidative cyclization in the presence of DDQ. The resulting 2-arylbenzoxazoles were separated from the reduced DDQ byproduct by treatment of reaction mixture with a strongly basic ion-exchange resin. The applicability of this chemistry to spatially separate library synthesis is demonstrated by the

  在DDQ存在下，诱导衍生自邻氨基苯酚与苯甲醛缩合的席夫碱进行氧化环化反应。通过用强碱性离子交换树脂处理反应混合物，从还原的DDQ副产物中分离出所得的2-芳基苯并恶唑。通过制备352个成员的文库，证明了该化学方法在空间上分离文库合成的适用性。