diethyl 2',3'-dihydro-1'-hydroxy-1-oxoindan[2,3-b]pyrrole-2',3'-dicarboxylate | 676620-07-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2',3'-dihydro-1'-hydroxy-1-oxoindan[2,3-b]pyrrole-2',3'-dicarboxylate
• CAS: 676620-07-8
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: OALBNMCXARNPTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.14
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl 2',3'-dihydro-1'-hydroxy-1-oxoindan[2,3-b]pyrrole-2',3'-dicarboxylate 在 PPA 作用下， 反应 1.0h， 以50%的产率得到
  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
• 作为产物：
  描述：

  1H-茚-1,2,3-三酮2-肟 、 乙氧甲酰基亚甲基三苯基膦 以 氯仿 为溶剂， 反应 24.0h， 以48%的产率得到ethyl 3'-hydroxy-1,3-dioxospiro[indan-2,5'-pyrrole-2'-carboxylate]
  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.