(+/-)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-one (E)-oxime

• 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: (+/-)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-one (E)-oxime
• 英文别名: pinocarvone oxime；(NE)-N-[(1S,5S)-6,6-dimethyl-2-methylidene-3-bicyclo[3.1.1]heptanylidene]hydroxylamine
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: VPNPPABHZOSKRQ-WGRRCAOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-one (E)-oxime 在 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.5h， 以54%的产率得到(+/-)-6,6-dimethyl-2-methylene-(10E)-nitrobicyclo[3.1.1]heptan-3-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
• 作为产物：
  描述：

  Pinene 生成 (+/-)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-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

• Synthesis of chiral pinopyridines using catalysis by metal complexes
  作者：Yuliya P. Ustimenko、Alexander M. Agafontsev、Aleksey V. Tkachev

  DOI：10.1007/s10593-022-03066-x

  日期：2022.2

  Methods for the preparation of pinopyridines from pinocarvone oxime or its ethers and alkenes (alkynes) using the C–H activation reaction were studied. Palladium complexes and Wilkinson's catalyst were chosen as the catalytic systems.

  研究了使用 C-H 活化反应从匹诺香芹酮肟或其醚和烯烃（炔烃）制备匹诺吡啶的方法。选择钯配合物和威尔金森催化剂作为催化体系。
• ——
  作者：P. A. Petukhov、S. N. Bizyaev、À. V. Tkachev

  DOI：10.1023/a:1015097200993

  日期：——

  The reaction of nitroso chlorides of natural monoterpene hydrocarbons, 3-carene and alpha-pinene, with simple alpha,omega-diamines (1,2-diaminoethane, 1,3-diaminopropane, piperazine, 1,6-diaminohexane, diethylenetriamine) results in the formation of alpha-amino oximes and bis-alpha-amino oximes. The product structures were proved by spectroscopy. The procedures of separation and purification of diamino oximes and diamino dioximes are described. Detailed analysis of the H-1 and C-13 NMR spectra of the new chiral nitrogen-containing derivatives was carried out.
• ——
  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).