5'-methylspiro[1,3-dioxoindan[2,3']-(2'H)-1',2'-oxazole]

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5'-methylspiro[1,3-dioxoindan[2,3']-(2'H)-1',2'-oxazole]
• 英文别名: 5-methylspiro[2H-1,2-oxazole-3,2'-indene]-1',3'-dione
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: UIRVAFOZKCARNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1H-茚-1,2,3-三酮2-肟 、 烯丙基三苯基溴化膦 在 lithium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以46%的产率得到1-oxo-2'-vinylindan[2,3-d]-1',3'-oxazole
  参考文献：
  名称：

  Synthesis of Spiro and Fused Five Membered N -Heterocycles from Alkylidenephosphoranes

  摘要：

  Triketoindan-2-oxime reacted readily with ethoxycarbonylmethylene triphenylphosphorane to give mainly the corresponding spiro-pyrrole (38%) along with the fused 1'-hydroxydihydropyrrole (14%), whereas the spiro-dimer (29%) was obtained from the reaction of the oxime with methoxycarbonylmethylenetriphenyl phosphorane in addition to the corresponding 1'-hydroxydihydropyffole (31%). Conversely, Wittig products, mono-olefin (52%) and diolefin (<7%) along with the reduced substrate (10%), were observed when the oxime was treated with a cyano ylide. The reactions of the oxime with allyl- and vinyl phosphonium salts proceeded under phase-transfer catalysis to afford fused oxazole (46%) and spiro[2]oxazole (17%), while with the latter the fused 1'-hydroxypyrrole (55%) was produced.

  DOI：

  10.1007/s00706-003-0047-8

文献信息

• Synthesis of Spiro and Fused Five Membered N -Heterocycles from Alkylidenephosphoranes
  作者：Wafaa M. Abdou、Mounir A. I. Salem、Ashraf A. Sediek

  DOI：10.1007/s00706-003-0047-8

  日期：2003.10.1

  Triketoindan-2-oxime reacted readily with ethoxycarbonylmethylene triphenylphosphorane to give mainly the corresponding spiro-pyrrole (38%) along with the fused 1'-hydroxydihydropyrrole (14%), whereas the spiro-dimer (29%) was obtained from the reaction of the oxime with methoxycarbonylmethylenetriphenyl phosphorane in addition to the corresponding 1'-hydroxydihydropyffole (31%). Conversely, Wittig products, mono-olefin (52%) and diolefin (<7%) along with the reduced substrate (10%), were observed when the oxime was treated with a cyano ylide. The reactions of the oxime with allyl- and vinyl phosphonium salts proceeded under phase-transfer catalysis to afford fused oxazole (46%) and spiro[2]oxazole (17%), while with the latter the fused 1'-hydroxypyrrole (55%) was produced.