ethyl 4-(oxazol-2-yl)benzoate | 1139705-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(oxazol-2-yl)benzoate
• 英文别名: 4-oxazol-2-yl-benzoic acid ethyl ester；Ethyl 4-(1,3-oxazol-2-yl)benzoate；ethyl 4-(1,3-oxazol-2-yl)benzoate
• CAS: 1139705-32-0
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: MLNHFECHMXWCEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(oxazol-2-yl)benzoate 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 ethyl 4-(5-benzoyl-4-(4-methoxyphenyl)oxazol-2-yl)benzoate
  参考文献：
  名称：

  Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn

  摘要：

  A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.

  DOI：

  10.1021/ol403019c
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 、 (1,3-恶唑-2-基)氯化锌 在 [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 18.0h， 以87%的产率得到ethyl 4-(oxazol-2-yl)benzoate
  参考文献：
  名称：

  加热到恶唑：非低温恶唑金属化和 Negishi 偶联开发

  摘要：

  本报告详细介绍了用于合成恶唑锌酸盐的几种合适的非低温金属化条件的开发。随后几轮高通量催化剂筛选最终导致了几种合适的 Pd 源的鉴定，这些 Pd 源可用于未取代恶唑的 Negishi 偶联。还介绍了报告条件之一的范围和一般性。

  DOI：

  10.1055/s-0037-1611909

文献信息

• Imidazolylsulfonates: Electrophilic Partners in Cross-Coupling Reactions
  作者：Jennifer Albaneze-Walker、Ravinder Raju、Jennifer A. Vance、Andrew J. Goodman、Michael R. Reeder、Jing Liao、Mathew T. Maust、Patrick A. Irish、Peter Espino、David R. Andrews

  DOI：10.1021/ol802381k

  日期：2009.4.2

  Aryl imidazolylsulfonates participate as electrophilic coupling partners in palladium-mediated cross-coupling reactions. The aryl imidazolylsulfonates display good stability while maintaining good reactivity in a variety of palladium-catalyzed coupling reactions. Imidazolylsulfonates are a practical and economic alternative to triflates.

  芳基咪唑基磺酸盐作为亲电偶联伙伴参与钯介导的交叉偶联反应。芳基咪唑基磺酸盐显示出良好的稳定性，同时在各种钯催化的偶联反应中保持良好的反应性。咪唑基磺酸盐是三氟甲磺酸酯的一种实用且经济的替代品。
• Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases of Mg and Zn
  作者：Diana Haas、Marc Mosrin、Paul Knochel

  DOI：10.1021/ol403019c

  日期：2013.12.20

  A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl center dot LiCl or TMPZnCl center dot LiCl led to the corresponding magnesiated or zincated species which were stable toward ring fragmentation. Furthermore, they readily reacted with various electrophiles, such as aryl and allylic halides, acid chlorides, TMSCl, and TMS-CN, providing highly functionalized oxazoles.
• Warming Up to Oxazole: Noncryogenic Oxazole Metalation and Negishi Coupling Development
  作者：Michael J. Geier、Xiaotian Wang、Luke D. Humphreys、Selcuk Calimsiz、Mark E. Scott

  DOI：10.1055/s-0037-1611909

  日期：2019.9

  details the development of several suitable noncryogenic metalation conditions for the synthesis of oxazole zincate. Subsequent rounds of high-throughput catalyst screening ultimately led to the identification of several suitable Pd sources that can be used for the Negishi coupling of unsubstituted oxazole. The scope and generality for one of the reported conditions is also presented.

  本报告详细介绍了用于合成恶唑锌酸盐的几种合适的非低温金属化条件的开发。随后几轮高通量催化剂筛选最终导致了几种合适的 Pd 源的鉴定，这些 Pd 源可用于未取代恶唑的 Negishi 偶联。还介绍了报告条件之一的范围和一般性。