4-(benzoxazol-2-yl)-N,N-diethylbenzamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(benzoxazol-2-yl)-N,N-diethylbenzamide
• 英文别名: 4-(1,3-benzoxazol-2-yl)-N,N-diethylbenzamide
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: ITACWRFUNNNJRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯并恶唑 、 N,N-diethyl-4-(methylthio)benzamide 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium t-butanolate 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以91%的产率得到4-(benzoxazol-2-yl)-N,N-diethylbenzamide
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Azoles or Thiazoles with Aryl Thioethers via C–H/C–S Activation

  摘要：

  Palladium-catalyzed cross-coupling via the (CspS)-S-2 bond activation of aryl thioethers and the C-H bond activation of azoles or thiazoles was carried out. Electron-deficient and -rich aryl methyl thioethers and diaryl thioethers can be employed as the coupling partners and the reaction tolerates a range of functional groups including MeO, CF3, CN, PhCO, CONEt2, and Py groups.

  DOI：

  10.1021/acs.orglett.5b00510

文献信息

• Ni-Catalyzed C−F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles
  作者：Youzhi Yin、Xiaoyu Yue、Qi Zhong、Hanmin Jiang、Ruopeng Bai、Yu Lan、Hua Zhang

  DOI：10.1002/adsc.201701506

  日期：2018.4.17

  A Ni‐catalyzed C−F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system. A rapid synthesis of natural product texaline was also demonstrated using this protocol. This transformation could be potentially utilized in regioselective

  已开发了以恶唑为偶合伴侣的未活化芳基氟化物的Ni催化C-F键官能化。在Ni（cod）2 / IMes催化体系存在下，可以以中等至良好的产率获得各种芳基化的恶唑。使用该方案还证明了天然产物texaline的快速合成。该转化可潜在地用于后期合成应用中恶唑基的区域选择性引入。
• Palladium-Catalyzed C–H Arylation of (Benzo)oxazoles or (Benzo)thiazoles with Aryltrimethylammonium Triflates
  作者：Feng Zhu、Jian-Long Tao、Zhong-Xia Wang

  DOI：10.1021/acs.orglett.5b02458

  日期：2015.10.2

  The C-H arylation of (benzo)oxazoles or (benzo)thiazoles with aryltrimethylammonium triflates was carried out via Pd-catalyzed C-H/C-N cleavage. Oxazoles, thiazoles, benzoxazole, and benzothiazole were arylated using activated and deactivated aryltrimethylamrnonium triflates to give 2-aryl(benzo)oxazoles or 2-aryl(benzo)thiazoles in reasonable to excellent yields.
• Palladium-Catalyzed Coupling of Azoles or Thiazoles with Aryl Thioethers via C–H/C–S Activation
  作者：Feng Zhu、Zhong-Xia Wang

  DOI：10.1021/acs.orglett.5b00510

  日期：2015.3.20

  Palladium-catalyzed cross-coupling via the (CspS)-S-2 bond activation of aryl thioethers and the C-H bond activation of azoles or thiazoles was carried out. Electron-deficient and -rich aryl methyl thioethers and diaryl thioethers can be employed as the coupling partners and the reaction tolerates a range of functional groups including MeO, CF3, CN, PhCO, CONEt2, and Py groups.