5-methoxycarbonyloxy-4-isopropyl-2-(4-methoxyphenyl)oxazole | 909122-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxycarbonyloxy-4-isopropyl-2-(4-methoxyphenyl)oxazole
• 英文别名: 2-(4-methoxyphenyl)-4-iso-propyloxazol-5-yl methyl carbonate；[2-(4-Methoxyphenyl)-4-propan-2-yl-1,3-oxazol-5-yl] methyl carbonate；[2-(4-methoxyphenyl)-4-propan-2-yl-1,3-oxazol-5-yl] methyl carbonate
• CAS: 909122-68-5
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: IAMLPIGYMFYSNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  419.6±55.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonyloxy-4-isopropyl-2-(4-methoxyphenyl)oxazole 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.08h， 以67%的产率得到4-isopropyl-5-oxo-2-(4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxylic acid methyl 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：

  4-isopropyl-2-(4-methoxyphenyl)oxazol-5(4H)-one 、 氯甲酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到5-methoxycarbonyloxy-4-isopropyl-2-(4-methoxyphenyl)oxazole
  参考文献：
  名称：

  Efficient N-Heterocyclic Carbene-Catalyzed O- to C-Acyl Transfer

  摘要：

  An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.

  DOI：

  10.1021/ol061380h

文献信息

• Efficient N-Heterocyclic Carbene-Catalyzed <i>O</i>- to C-Acyl Transfer
  作者：Jennifer E. Thomson、Kathryn Rix、Andrew D. Smith

  DOI：10.1021/ol061380h

  日期：2006.8.1

  An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.
• Enantioselective Construction of Quaternary Stereocenters:  Rearrangements of <i>O</i>-Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridine
  作者：J. Craig Ruble、Gregory C. Fu

  DOI：10.1021/ja982890c

  日期：1998.11.1
• 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.