(E)-6-ethylidene-7-(2-oxo-2-phenylethyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one | 1310823-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-6-ethylidene-7-(2-oxo-2-phenylethyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
• CAS: 1310823-59-6
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: KVKBMYLCDKFZIH-FUQNDXKWSA-N

反应信息

• 作为反应物：
  描述：

  (E)-6-ethylidene-7-(2-oxo-2-phenylethyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到7-(2-oxo-2-phenylethyl)dihydropyrrolo[1,2-c]oxazole-3,6(1H,5H)-dione
  参考文献：
  名称：

  Enone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles

  摘要：

  The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dicarbonyl intermediate are avoided. Classes of pyrroles that are accessible by this approach include 2,3-, 2,4-, 1,2,3-, 1,2,4-, 2,3,5-, and 1,2,3,5-substituted monocyclic pyrroles as well as a number of fused-ring polycyclic derivatives.

  DOI：

  10.1021/ol201133n
• 作为产物：
  描述：

  (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)-3-(prop-2-yn-1-yl)oxazolidin-2-one 、 Dimethylzinc 在 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.17h， 以72%的产率得到(E)-6-ethylidene-7-(2-oxo-2-phenylethyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
  参考文献：
  名称：

  Enone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles

  摘要：

  The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dicarbonyl intermediate are avoided. Classes of pyrroles that are accessible by this approach include 2,3-, 2,4-, 1,2,3-, 1,2,4-, 2,3,5-, and 1,2,3,5-substituted monocyclic pyrroles as well as a number of fused-ring polycyclic derivatives.

  DOI：

  10.1021/ol201133n