benzo[d]oxazole | 1260071-21-3

• 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: benzo[d]oxazole
• 英文别名: 5-(4-trifluoromethylphenyl)benzoxazole；5-[4-(Trifluoromethyl)phenyl]-1,3-benzoxazole
• CAS: 1260071-21-3
• 化学式: C₁₄H₈F₃NO
• 分子量: 263.219
• InChiKey: WSDRBOQPMHKPTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzo[d]oxazole 、 二甲胺基磺酰氯 在 potassium dichromate 、 (2,2-联吡啶)二氯钯(II) 、 copper(l) cyanide 、 potassium carbonate 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以86%的产率得到N,N-dimethyl-5-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-2-amine
  参考文献：
  名称：

  Palladium–copper-catalyzed desulfitative amination of benzo[d]oxazole C–H bond

  摘要：

  An efficient palladium-copper-catalyzed direct C-H amination of substituted benzoxazoles with various sulfamoyl chlorides as nitrogen group sources has been developed. The system does not need a strong base and tolerates a series of functional groups, such as chloro, methyl, and nitro groups, providing the amination products in moderate to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.044
• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 5-氯苯并唑 在 potassium phosphate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 为溶剂， 生成 benzo[d]oxazole
  参考文献：
  名称：

  铜催化的C直接羰基化？二氧化碳的H键

  摘要：

  天然气烹饪：铜络合物是出色的催化剂，可将芳族杂环CH键与CO 2直接羧化，从而为杂环羧酸酯的合成提供了一种经济，环境友好的工艺（请参见方案; IPr = 1,3-双（2,6-二异丙基苯基）咪唑-2-亚基）。已经分离出该反应的一些活性中间体并对其结构进行了表征。

  DOI：

  10.1002/anie.201003995

文献信息

• Direct Copper-Catalyzed C-H Monofluoroalkylation of Benzoxazoles with 1-Fluoro-1-haloalkanes
  作者：Wei Li、Andrii Varenikov、Mark Gandelman

  DOI：10.1002/ejoc.201901929

  日期：2020.6.8

  Copper‐catalyzed cross‐coupling reaction allowed the first direct C–H monofluoroalkylation of benzoxazole with 1‐fluoro‐1‐haloalkanes, which bear β‐hydrogens and no directing groups in vicinity to the reaction center.

  铜催化的交叉偶联反应使苯并恶唑首次与1-氟-1-卤代烷烃进行直接C–H单氟烷基化反应，后者带有β-氢且在反应中心附近没有任何导向基团。
• The palladium-catalyzed tandem decarboxylation, carbon–carbon triple bond oxidation and decarbonylative arylation of the benzoxazole C–H bond
  作者：Dongfang Liu、Bin Liu、Jiang Cheng

  DOI：10.1039/c3ra41185k

  日期：——

  A palladium-catalyzed arylation of benzoxazole has been developed. This protocol involves the tandem decarboxylation and oxidation of a carbon–carbon triple bond followed by decarbonylative arylation of the benzoxazole C–H bond.

  开发了一种钯催化的苯并恶唑芳基化反应。该方案涉及碳-碳三键的串联脱羧和氧化，随后是苯并恶唑C-H键的脱羰基芳基化。
• 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。
• Copper-Catalyzed Direct Carboxylation of CH Bonds with Carbon Dioxide
  作者：Liang Zhang、Jianhua Cheng、Takeshi Ohishi、Zhaomin Hou

  DOI：10.1002/anie.201003995

  日期：2010.11.8

  Cooking with gas: Copper complexes serve as excellent catalysts for the direct carboxylation of aromatic heterocyclic CH bonds with CO2, thereby offering an economical and environmentally benign process for the synthesis of heterocyclic carboxylic esters (see scheme; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene). Some active intermediates of this reaction have been isolated and structurally

  天然气烹饪：铜络合物是出色的催化剂，可将芳族杂环CH键与CO 2直接羧化，从而为杂环羧酸酯的合成提供了一种经济，环境友好的工艺（请参见方案; IPr = 1,3-双（2,6-二异丙基苯基）咪唑-2-亚基）。已经分离出该反应的一些活性中间体并对其结构进行了表征。
• Palladium–copper-catalyzed desulfitative amination of benzo[d]oxazole C–H bond
  作者：Shuyou Chen、Kui Zheng、Fan Chen

  DOI：10.1016/j.tetlet.2012.09.044

  日期：2012.11

  An efficient palladium-copper-catalyzed direct C-H amination of substituted benzoxazoles with various sulfamoyl chlorides as nitrogen group sources has been developed. The system does not need a strong base and tolerates a series of functional groups, such as chloro, methyl, and nitro groups, providing the amination products in moderate to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.