2-(1-Methyl-2-cyan-aethyl)-cyclohexanon | 7647-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-Methyl-2-cyan-aethyl)-cyclohexanon
• 英文别名: 3-<2-Oxo-cyclohexyl>-butyronitril；3-Methyl-3-<2-oxo-cyclohexyl>-propionitril；3-(2-oxocyclohexyl)butanenitrile
• CAS: 7647-27-0
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: GUTKARKYKFZADS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(1-Methyl-2-cyan-aethyl)-cyclohexanon 在 sodium ethanolate 、 sodium acetate 、 二氧化氮 作用下， 生成 7-Methyl-bicyclo<4.2.1>nonan-9-on
  参考文献：
  名称：

  Ring enlargements. XI. Structural influences on the course of the intramolecular diazo alkane-carbonyl reaction

  摘要：

  DOI：

  10.1021/jo01279a078
• 作为产物：
  描述：

  环己酮 、 烯丙基腈 生成 2-(1-Methyl-2-cyan-aethyl)-cyclohexanon
  参考文献：
  名称：

  Ring enlargements. XI. Structural influences on the course of the intramolecular diazo alkane-carbonyl reaction

  摘要：

  DOI：

  10.1021/jo01279a078

文献信息

• Reaction of Aliphatic Ketones with α-Cyano-α, β-unsaturated Acid Derivatives
  作者：Kikumasa Sato、Yoshie Kurihara、Seiichi Inoue

  DOI：10.1246/bcsj.40.942

  日期：1967.4

  the acid with methyl ethyl ketone, cyclohexanone, and ethyl laevulinate. The reaction of ketones with ethyl ethylidenecyanoacetate did not afford Knovenagel-type condensates, but Michael-type adducts in appreciable yields, for example, ethyl 2-cyano-3,4-dimethyl-5-oxohexanoate from methyl ethyl ketone. Diethyl ethylidenemalonate also gave Michael-type adducts. These results seem to suggest that the

  已经研究了几种脂肪族酮与 α-氰基-α, β-不饱和酸衍生物的反应。亚乙基氰基乙酸在 150-160°C 的高压釜中与大量过量的丙酮反应生成 3-甲基-5-氧代己腈，这被认为是由丙酮的迈克尔型加合物脱羧到酸上产生的。通过酸与甲基乙基酮、环己酮和乙酰丙酸乙酯的反应获得类似的加合物。酮与乙基亚乙基氰基乙酸乙酯的反应没有提供 Knovenagel 型缩合物，而是以可观的产率提供 Michael 型加合物，例如，来自甲基乙基酮的 2-氰基-3,4-二甲基-5-氧代己酸乙酯。亚乙基丙二酸二乙酯也产生迈克尔型加合物。
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.