Benzyl-(2-hydroxy-5,5-dimethyl-3,7-dioxocyclohept-1-en-1-carboxylat) | 374752-74-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Benzyl-(2-hydroxy-5,5-dimethyl-3,7-dioxocyclohept-1-en-1-carboxylat)
• 英文别名: Benzyl 2-hydroxy-5,5-dimethyl-3,7-dioxocycloheptene-1-carboxylate；benzyl 2-hydroxy-5,5-dimethyl-3,7-dioxocycloheptene-1-carboxylate
• CAS: 374752-74-6
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: RMJUDKURHXOOET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl-(2-hydroxy-5,5-dimethyl-3,7-dioxocyclohept-1-en-1-carboxylat) 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以47%的产率得到6,6-Dimethylcycloheptan-1,4-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：

  5,5-dimethyl-cyclohexane-1,2,3-trione 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 Benzyl-(2-hydroxy-5,5-dimethyl-3,7-dioxocyclohept-1-en-1-carboxylat)
  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

文献信息

• 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
  作者：Kurt Schank、Luigi La Vecchia、Carlo Lick

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

  日期：2001.7.11

  Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds (`1,2,3-Triones'). Part 1. Reaction of Diazomethane and Its Derivatives with 5,5-Dimethylcyclohexane-1,2,3-trione (=`Oxo-dimedone') and Related Cyclohexane-1,2,3-triones 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