naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole-4-carboxylate | 1312808-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole-4-carboxylate
• 英文别名: Naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-1,3-oxazole-4-carboxylate
• CAS: 1312808-05-1
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: HJAPLPAKYNDXIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)-4-methyloxazol-5-yl naphthalen-1-yl carbonate 在 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole-4-carboxylate
  参考文献：
  名称：

  Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

  摘要：

  The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.001

文献信息

• 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。
• Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes
  作者：Craig D. Campbell、Carmen Concellón、Andrew D. Smith

  DOI：10.1016/j.tetasy.2011.04.001

  日期：2011.4

  The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs. (C) 2011 Elsevier Ltd. All rights reserved.