2-methyl-3-nitrocyclohex-2-en-1-one (E)-oxime

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-methyl-3-nitrocyclohex-2-en-1-one (E)-oxime
• 英文别名: (NE)-N-(2-methyl-3-nitrocyclohex-2-en-1-ylidene)hydroxylamine
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: WQRCTUARJGRIHZ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基-1-环己烯 在 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 2-methyl-3-nitrocyclohex-2-en-1-one (E)-oxime
  参考文献：
  名称：

  摘要：

  Using a number of cyclic alpha,beta-unsaturated oximes of the terpene series and sonic Simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom it the beta-carbon atom were demonstrated to be converted into beta-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C-C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).

  DOI：

  10.1023/a:1012785007135

文献信息

• GRANT, R. D.;PINHEY, J. T., AUSTRAL. J. CHEM., 1984, 37, N 6, 1231-1244
  作者：GRANT, R. D.、PINHEY, J. T.

  DOI：——

  日期：——
• ——
  作者：A. M. Chibiryaev、A. Yu. Denisov、D. V. Pyshnyi、A. V. Tkachev

  DOI：10.1023/a:1012785007135

  日期：——

  Using a number of cyclic alpha,beta-unsaturated oximes of the terpene series and sonic Simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom it the beta-carbon atom were demonstrated to be converted into beta-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C-C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).