diethyl (2'-ethyl-1,3,5'-trioxo-1H,3H,5'H-spiro[indane-2,3'-4'H-isooxazol]-4'-yl)phosphonate | 1148119-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: diethyl (2'-ethyl-1,3,5'-trioxo-1H,3H,5'H-spiro[indane-2,3'-4'H-isooxazol]-4'-yl)phosphonate
• 英文别名: 4-Diethoxyphosphoryl-2-ethylspiro[1,2-oxazolidine-3,2'-indene]-1',3',5-trione
• CAS: 1148119-28-1
• 化学式: C₁₇H₂₀NO₇P
• 分子量: 381.322
• InChiKey: NYZYNFHBTVWJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 diethyl (2'-ethyl-1,3,5'-trioxo-1H,3H,5'H-spiro[indane-2,3'-4'H-isooxazol]-4'-yl)phosphonate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以88%的产率得到methyl [4'(diethoxyphosphonyl)-2'-ethyl-3,5'-dioxo-1H,3H,5'H-spiro[indene-2,3'-4'H-isooxazol]-1-ylidene]acetate
  参考文献：
  名称：

  An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions

  摘要：

  Treatment of triketoindan-2-oxime with alpha-phosphonyl carbanions in sodium ethanolate solution at reflux temperature led to a number of the corresponding substituted spiroisooxazole-, fused 1,3-oxazole, and 1,4-oxazine phosphor esters in moderate to high yields. Mechanisms for the formation of five- and six-membered rings are provided. A comparison of Wittig-Horner and Wittig reagent counterparts in reactions with the oxime is discussed. The various biological properties of selected examples of the synthesized products were studied.

  DOI：

  10.1007/s00706-007-0806-z
• 作为产物：
  描述：

  膦酰基乙酸甲酯二乙酯 、 1H-茚-1,2,3-三酮2-肟 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以42%的产率得到diethyl (2'-ethyl-1,3,5'-trioxo-1H,3H,5'H-spiro[indane-2,3'-4'H-isooxazol]-4'-yl)phosphonate
  参考文献：
  名称：

  An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions

  摘要：

  Treatment of triketoindan-2-oxime with alpha-phosphonyl carbanions in sodium ethanolate solution at reflux temperature led to a number of the corresponding substituted spiroisooxazole-, fused 1,3-oxazole, and 1,4-oxazine phosphor esters in moderate to high yields. Mechanisms for the formation of five- and six-membered rings are provided. A comparison of Wittig-Horner and Wittig reagent counterparts in reactions with the oxime is discussed. The various biological properties of selected examples of the synthesized products were studied.

  DOI：

  10.1007/s00706-007-0806-z

文献信息

• An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions
  作者：Wafaa M. Abdou、Ashraf A. Sediek、Maha D. Khidre

  DOI：10.1007/s00706-007-0806-z

  日期：2008.6

  Treatment of triketoindan-2-oxime with alpha-phosphonyl carbanions in sodium ethanolate solution at reflux temperature led to a number of the corresponding substituted spiroisooxazole-, fused 1,3-oxazole, and 1,4-oxazine phosphor esters in moderate to high yields. Mechanisms for the formation of five- and six-membered rings are provided. A comparison of Wittig-Horner and Wittig reagent counterparts in reactions with the oxime is discussed. The various biological properties of selected examples of the synthesized products were studied.