Ethyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat] | 374752-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat]
• CAS: 374752-67-7
• 化学式: C₁₂H₁₆N₂O₅
• 分子量: 268.269
• InChiKey: UNFVGCMNZFXFAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  117.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Ethyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat] 在 盐酸 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 2.0h， 生成 5,5-Dimethyl-3-oxocyclohex-1-en-1-carbonsaeure
  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：

  重氮乙酸乙酯 、 5,5-dimethyl-cyclohexane-1,2,3-trione 以 乙醚 为溶剂， 反应 1.5h， 以77%的产率得到Ethyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat]
  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