naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole-4-carboxylate | 1318802-51-5

• 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 (4R)-2-(4-methoxyphenyl)-4-methyl-5-oxo-1,3-oxazole-4-carboxylate
• CAS: 1318802-51-5
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: HJAPLPAKYNDXIS-JOCHJYFZSA-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 、 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl phenyl carbonate 在 (S)-5-benzyl-6,6-dimethyl-2-phenyl-5,6-dihydrooxazolo[2,3-c][1,2,4]triazol-2-ium tetrafluoroborate 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 生成 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl naphthalen-1-yl carbonate 、 naphthalen-1-yl 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole-4-carboxylate 、 naphthalen-1-yl 4-benzyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole-4-carboxylate 、 5-phenoxycarbonyl-4-methyl-2-(4-methoxyphenyl)-oxazole 、 4-methyl-5-oxo-2-(4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxylic acid phenyl ester 、 4-benzyl-5-oxo-2-(4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxylic acid phenyl ester
  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

• 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.