2-(2-benzoyl-5-methylphenyl)benzoxazole | 1415419-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-benzoyl-5-methylphenyl)benzoxazole
• 英文别名: [2-(1,3-Benzoxazol-2-yl)-4-methylphenyl]-phenylmethanone
• CAS: 1415419-65-6
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: JJNRYUWFDGIIRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3-甲基苯基)-1,3-苯并恶唑 、 苯甲醛 在 叔丁基过氧化氢 、 palladium diacetate 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 8.0h， 以78%的产率得到2-(2-benzoyl-5-methylphenyl)benzoxazole
  参考文献：
  名称：

  Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles

  摘要：

  An efficient and facile catalytic protocol for benzoxazole-directed ortho-acylation of 2-arylbenzoxazoles has been described using aldehydes as the easily accessible acyl source. This catalytic system was performed in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant in chlorobenzene, affording the acylated 2-arylbenzoxazoles in moderate to good yields. The acylation exhibited high regioselectivity for the substrates containing a meta-substituent in the benzene ring and typically occurred at the less sterically hindered ortho-C-H bond of the directing group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.033

文献信息

• Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles using arylmethyl alcohols as the acyl source
  作者：Qian Zhang、Fan Yang、Yangjie Wu

  DOI：10.1016/j.tet.2013.04.052

  日期：2013.6

  A facile and efficient way for the synthesis of the acylated 2-arylbenzoxazoles and 2-arylbenzothiazoles by heterocycle-directed ortho-acylation was developed. This reaction was performed in chlorobenzene, using arylmethyl alcohols and tert-butyl hydroperoxide (TBHP) as the easily accessible acyl source and the oxidant, respectively, affording the desired products in moderate to good yields.

  开发了一种简便有效的方法，该方法通过杂环导向的邻位酰化反应来合成酰化的2-芳基苯并恶唑和2-芳基苯并噻唑。该反应在氯苯中进行，分别使用芳基甲醇和叔丁基过氧化氢（TBHP）作为容易获得的酰基源和氧化剂，以中等至良好的收率提供所需的产物。
• Palladium-catalyzed oxidative ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles with toluene derivatives
  作者：Yong Zheng、Wei-Bin Song、Shu-Wei Zhang、Li-Jiang Xuan

  DOI：10.1016/j.tet.2015.01.025

  日期：2015.3

  A palladium-catalyzed oxidative ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles using TBHP as oxidant was developed, in which readily available toluene derivatives were used as the in situ generated acyl sources. This reaction afforded the desired products in moderate to good yields, and exhibited excellent regioselectivity. The plausible mechanism was also proposed.

  开发了使用TBHP作为氧化剂的钯催化的2-芳基苯并恶唑和2-芳基苯并噻唑的氧化邻位酰化反应，其中易得的甲苯衍生物用作原位生成的酰基源。该反应以中等至良好的产率提供了所需的产物，并表现出优异的区域选择性。还提出了合理的机制。