6-(cyclohex-1-en-1-yl)-2-diazo-3-oxohexanenitrile | 1431791-60-4

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 6-(cyclohex-1-en-1-yl)-2-diazo-3-oxohexanenitrile
• CAS: 1431791-60-4
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: MHCGVLMGOCBBMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  77.26
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(cyclohex-1-en-1-yl)-2-diazo-3-oxohexanenitrile 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 以82%的产率得到4-oxodecahydrocyclopropa[1,2:1,3]dibenzene-4a-carbonitrile
  参考文献：
  名称：

  α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

  摘要：

  An investigation of the intramolecular cyclopropanation reactions of alpha-diazo-beta-ketonitriles is reported. These studies reveal that alpha-diazo-beta-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. alpha-Diazo-beta-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the alpha-cyano-alpha-ketocyclopropane products are demonstrated to serve as substrates for S(N)2, S(N)2', and aldehyde cycloaddition reactions.

  DOI：

  10.1021/ja401610p
• 作为产物：
  描述：

  6-(cyclohex-1-en-1-yl)-3-oxohexanenitrile 在 吡啶 、 1H-咪唑-1-磺酰叠氮 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以82%的产率得到6-(cyclohex-1-en-1-yl)-2-diazo-3-oxohexanenitrile
  参考文献：
  名称：

  α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

  摘要：

  An investigation of the intramolecular cyclopropanation reactions of alpha-diazo-beta-ketonitriles is reported. These studies reveal that alpha-diazo-beta-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor acceptor-substituted diazo substrates instead produce mixtures of C-H insertion and dimerization products. alpha-Diazo-beta-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the alpha-cyano-alpha-ketocyclopropane products are demonstrated to serve as substrates for S(N)2, S(N)2', and aldehyde cycloaddition reactions.

  DOI：

  10.1021/ja401610p