Spiro[4.5]decan-7,8,9-trion | 374752-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Spiro[4.5]decan-7,8,9-trion
• 英文别名: Spiro[4.5]decane-7,8,9-trione
• CAS: 374752-55-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VQUYZVOGCGGZKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Spiro[4.5]decan-7,8,9-trion 以 乙醚 为溶剂， 反应 1.0h， 以19%的产率得到8-{6,7-Dihydro-7-oxospiro[1,3-benzodioxol-5(4H),1'-cyclopentan]-2-yl}-8-hydroxyspiro[4.5]decan-7,9-dion
  参考文献：
  名称：

  Chemie freier, cyclischer vicinaler Tricarbonyl-Verbindungen (`1,2,3-Trione'), Teil 1, Reaktionsweise von Diazomethan und seinen Derivaten mit 5,5-Dimethylcyclohexan-1,2,3-trion (=`Oxo-dimedon') und verwandten Cyclohexan-1,2,3-trionen

  摘要：

  Interactions of diazomethane and of its derivatives as typical nucleophiles with cyclic 1,2,3-triones as efficient electrophiles lead to different results: a) formation of oxiranes (C,O insertion under loss of N-2), b) nucleophilic addition yielding diazoaldols, c) formation of ring-enlargement products (C,C insertion under loss of N-2), and d) formation of dioxoles via redox reactions (under loss of N-2). Our results and those of other groups allow us to recognize that the unexpected outcome of the reaction of oxodimedone and several related species is due to a closed-shell diazoaldol formation followed by an open-shell redox reaction leading to dioxoles.

  DOI：

  10.1002/1522-2675(20010711)84:7<2071::aid-hlca2071>3.0.co;2-d
• 作为产物：
  描述：

  1-cyclopentylidenepropan-2-one 在 氧气 、 sodium carbonate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 Spiro[4.5]decan-7,8,9-trion
  参考文献：
  名称：

  Chemie freier, cyclischer vicinaler Tricarbonyl-Verbindungen (`1,2,3-Trione'), Teil 1, Reaktionsweise von Diazomethan und seinen Derivaten mit 5,5-Dimethylcyclohexan-1,2,3-trion (=`Oxo-dimedon') und verwandten Cyclohexan-1,2,3-trionen

  摘要：

  Interactions of diazomethane and of its derivatives as typical nucleophiles with cyclic 1,2,3-triones as efficient electrophiles lead to different results: a) formation of oxiranes (C,O insertion under loss of N-2), b) nucleophilic addition yielding diazoaldols, c) formation of ring-enlargement products (C,C insertion under loss of N-2), and d) formation of dioxoles via redox reactions (under loss of N-2). Our results and those of other groups allow us to recognize that the unexpected outcome of the reaction of oxodimedone and several related species is due to a closed-shell diazoaldol formation followed by an open-shell redox reaction leading to dioxoles.

  DOI：

  10.1002/1522-2675(20010711)84:7<2071::aid-hlca2071>3.0.co;2-d