N-butyl-2-phenyloxazole-4-carboxamide | 1284215-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-butyl-2-phenyloxazole-4-carboxamide
• 英文别名: N-ⁿbutyl 2-phenyloxazole-4-formamide；N-n-butyl 2-phenyloxazole-4-formamide
• CAS: 1284215-71-9
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: AVFUYECJKIYVCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.13
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-butyl-2-phenyloxazole-4-carboxamide 在 silver(I) acetate 、 palladium diacetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以76%的产率得到N,N'-di-n-butyl 2,2'-diphenyl-bis-5,5'-oxazole-4,4'-diformamide
  参考文献：
  名称：

  Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives

  摘要：

  An efficient Pd(OAc)(2)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives is described. It represents a facile and practical methodology to prepare bis-5,5'-thiazole (oxazole)-4,4'-dicarboxylic derivatives in good to excellent yields. This protocol tolerates a series of substitutions on the thiazole (oxazole) rings, including alkyl, carbonyl, and electron-withdrawing/donating group substituted phenyl groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.123
• 作为产物：
  描述：

  在 氧气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以82%的产率得到N-butyl-2-phenyloxazole-4-carboxamide
  参考文献：
  名称：

  Environmental-benign oxidation of 2-oxazolines to oxazoles by dioxygen as the sole oxidant

  摘要：

  A facile and environment-benign oxidation by dioxygen as the sole oxidant was applied for the conversion of 2-oxazolines to oxazoles. The substituent effect on 2-oxazoline ring was investigated. The use of this methodology for the synthesis of a key intermediate of a CDC25 phosphatase inhibitor (SC-alpha alpha delta 9) as an anticancer agent was also described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.050

文献信息

• Metal-free C–H amination of arene with <i>N</i>-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature
  作者：Qi Miao、Zhong Shao、Cuiying Shi、Lifang Ma、Fang Wang、Ruoqi Fu、Haochen Gao、Ziyuan Li

  DOI：10.1039/c9cc02739d

  日期：——

  amination of arene through C–H bond cleavage employing N-fluorobenzenesulfonimide (NFSI) as the amination reagent in good to excellent yields with broad arene scope in the absence of any metal, ligand or additive is reported. Unlike previous transition metal-catalysed aminations in which high reaction temperatures are usually necessary, this novel reaction at room temperature is the first example of C–H

  据报道，在不使用任何金属，配体或添加剂的情况下，使用N-氟苯磺酰亚胺（NFSI）作为胺化试剂，通过TEMP键催化的芳烃通过C–H键断裂的直接胺化反应具有良好的收率和优异的收率。与以前通常需要高反应温度的过渡金属催化胺化反应不同，这种在室温下的新颖反应是通过有机催化实现的NFSI的C–H胺化反应的第一个例子。还提出了这种简洁胺化的可能机理。
• DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation
  作者：Bowen Lei、Xiaojiao Wang、Lifang Ma、Huixuan Jiao、Lisi Zhu、Ziyuan Li

  DOI：10.1039/c7ob01083d

  日期：——

  A novel and concise C5-alkylation of oxazole using alkylboronic acids as the alkyl donor via Pd(II)-catalysed C-H bond activation has been achieved in moderate to good yields with satisfactory functional group tolerance. Instead of commonly used BQ as a key promoter, DDQ was discovered to be a better additive that significantly promoted this alkylation. This efficient and advanced method represents

  使用烷基硼酸作为烷基供体通过Pd（II）催化的CH键活化，实现了新颖简明的恶唑C5-烷基化反应，具有中等至良好的收率，并具有令人满意的官能团耐受性。发现DDQ替代了通常使用的BQ作为关键促进剂，它是一种显着促进这种烷基化的更好的添加剂。这种高效，先进的方法代表了在恶唑的C5位上的第一个C（sp2）-C（sp3）交叉偶联反应，由于其在含恶唑生物活性分子的后期功能化中的潜在应用而特别引人注目。