methyl 5-oxo-2-(p-tolylamino)-4,5-dihydrofuran-3-carboxylate | 1355579-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-oxo-2-(p-tolylamino)-4,5-dihydrofuran-3-carboxylate
• 英文别名: methyl 5-(4-methylanilino)-2-oxo-3H-furan-4-carboxylate
• CAS: 1355579-91-7
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: OOAKQRXAAIQPQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methylbenzonitrile oxide 、 methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 在 dirhodium(II) tetrakis(perfluorobutyrate) 、 copper(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到methyl 5-oxo-2-(p-tolylamino)-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates

  摘要：

  Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.

  DOI：

  10.1021/ol203331r

文献信息

• Substrate-Dependent Divergent Outcomes from Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides: Azabicyclo[3.1.0]hexanes or 5-Arylaminofuran-2(3<i>H</i>)-ones
  作者：Xinfang Xu、Dmitry Shabashov、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/jo3006733

  日期：2012.6.15

  Dirhodium(II)-catalyzed reactions of silyl-protected enol diazoacetates with nitrile oxides exhibit high nitrile oxide substituent dependence in the production rearrangement products via dipolar cycloaddition and either the Neber rearrangement or the Lossen rearrangement.
• Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3<i>H</i>)-one-4-carboxylates
  作者：Xinfang Xu、Dmitry Shabashov、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/ol203331r

  日期：2012.2.3

  Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.