phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-4,5-dihydrooxazole-4-carboxylate | 1017848-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-4,5-dihydrooxazole-4-carboxylate
• 英文别名: phenyl 2-(4-methoxyphenyl)-4-phenyl-5-oxo-4,5-dihydrooxazole-4-carboxylate；Phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-1,3-oxazole-4-carboxylate；phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-1,3-oxazole-4-carboxylate
• CAS: 1017848-87-1
• 化学式: C₂₃H₁₇NO₅
• 分子量: 387.392
• InChiKey: UDMFOCPGSZDHDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-4,5-dihydrooxazole-4-carboxylate 在 silica gel 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 生成 N-(p-anisoyl)phenylglycine phenyl ester
  参考文献：
  名称：

  Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates

  摘要：

  Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

  DOI：

  10.1021/jo702720a
• 作为产物：
  描述：

  5-phenoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-oxazole 在 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到phenyl 2-(4-methoxyphenyl)-5-oxo-4-phenyl-4,5-dihydrooxazole-4-carboxylate
  参考文献：
  名称：

  NHC中的有机碱效应促进了O-到C-羧基的转移；化学选择性概况，机理研究和多米诺骨牌催化†

  摘要：

  由NEt 3原位产生的由三唑啉亚基促进的碳酸恶唑基碳酸酯的O - C羧基转移与由KHMDS生成的三唑啉亚基促进的相同反应显示出明显不同的速率和化学选择性。通过广泛的交叉研究探索了这些途径的机制，以了解这一过程。尽管手性NHC在这些多米诺反应过程中仅产生适度水平的不对称诱导（<15％ee），但使用NEt 3作为碱基可以开发出多米诺骨牌多步反应序列。

  DOI：

  10.1039/c1ob05160a

文献信息

• Amidine catalysed O- to C-carboxyl transfer of heterocyclic carbonate derivatives
  作者：Caroline Joannesse、Carmen Simal、Carmen Concellón、Jennifer E. Thomson、Craig D. Campbell、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1039/b805850d

  日期：——

  The structural requirements of amidines necessary to act as efficient O- to C-carboxyl transfer agents are delineated and the scope of this process outlined through its application to a range of oxazolyl, benzofuranyl and indolyl carbonates.

  为了成为有效的O向C羧基转移剂，胍基的结构要求被阐明，并通过应用于一系列噁唑基、苯并呋喃基和吲哚基碳酸酯来概述该过程的范围。
• Tandem multi-step synthesis of C-carboxyazlactones promoted by N-heterocyclic carbenes
  作者：Craig D. Campbell、Nicolas Duguet、Katherine A. Gallagher、Jennifer E. Thomson、Anita G. Lindsay、AnnMarie C. O’Donoghue、Andrew D. Smith

  DOI：10.1039/b806816j

  日期：——

  Cascade reaction sequences incorporating N-heterocyclic carbene-based organocatalysis have been developed that allow the direct preparation of a range of (±)-4-phenoxycarbonylazlactones in good isolated yields (66–84%) from the corresponding N-p-anisoyl amino acids.

  已开发出结合N-杂环卡宾基础的有机催化的级联反应序列，这些反应序列可以直接从相应的N-p-安尼酰氨基酸制备一系列(±)-4-苯氧基羧基亚内酯，且纯品得率较高（66–84%）。
• Probing the Efficiency of N-Heterocyclic Carbene Promoted <i>O</i>- to C-Carboxyl Transfer of Oxazolyl Carbonates
  作者：Jennifer E. Thomson、Craig D. Campbell、Carmen Concellón、Nicolas Duguet、Kathryn Rix、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/jo702720a

  日期：2008.4.1

  Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.
• Organic base effects in NHC promoted O- to C-carboxyl transfer; chemoselectivity profiles, mechanistic studies and domino catalysis
  作者：Craig D. Campbell、Christopher J. Collett、Jennifer E. Thomson、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1039/c1ob05160a

  日期：——

  The O- to C-carboxyl transfer of oxazolyl carbonates promoted by triazolinylidenes, generated in situ with NEt3, shows a markedly different rate and chemoselectivity profile to the same reaction promoted by triazolinylidenes generated using KHMDS. The mechanism of these pathways has been probed through extensive crossover studies to understand this process. The use of NEt3 as a base allows domino multi-step

  由NEt 3原位产生的由三唑啉亚基促进的碳酸恶唑基碳酸酯的O - C羧基转移与由KHMDS生成的三唑啉亚基促进的相同反应显示出明显不同的速率和化学选择性。通过广泛的交叉研究探索了这些途径的机制，以了解这一过程。尽管手性NHC在这些多米诺反应过程中仅产生适度水平的不对称诱导（<15％ee），但使用NEt 3作为碱基可以开发出多米诺骨牌多步反应序列。