(1S,2S,5S)-5-isopropenyl-2-methyl-3-oxo-cyclohexane-1-carbonitrile | 137625-68-4

• 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: (1S,2S,5S)-5-isopropenyl-2-methyl-3-oxo-cyclohexane-1-carbonitrile
• 英文别名: S(+)-3-cyano-dihydrocarvone；(-)-(5S,3S,2S)-5-(methylethenyl)-3-cyano-2-methylcyclohexanone；(1S,2S,5S)-2-methyl-3-oxo-5-(prop-1-en-2-yl)cyclohexanecarbonitrile；(1S)-3-oxo-2c-methyl-5t-isopropenyl-cyclohexane-carbonitrile-(1r)；(1S)-3-Oxo-2c-methyl-5t-isopropenyl-cyclohexan-carbonitril-(1r)；5-Isopropenyl-2-methyl-3-oxocyclohexanecarbonitrile；(1S,2S,5S)-2-methyl-3-oxo-5-prop-1-en-2-ylcyclohexane-1-carbonitrile
• CAS: 137625-68-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: VRUMBVSOGMYXKH-LPEHRKFASA-N

物化性质

• 熔点：
  95.5 °C
• 沸点：
  310.7±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,5S)-5-isopropenyl-2-methyl-3-oxo-cyclohexane-1-carbonitrile 在 potassium cyanide 、 乙醇 、 溶剂黄146 作用下， 生成 (2S)-1ξ-hydroxy-2r-methyl-5t-isopropenyl-cyclohexane-dicarbonitrile-(1ξ.3c)
  参考文献：
  名称：

  Abe, Science reports of the Tokyo Bunrika Daigaku, section A. Mathematics, physics, chemistry., 1938, vol. 3, p. 217,227

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S)-1ξ-amino-2r-methyl-5t-isopropenyl-cyclohexane-dicarbonitrile-(1ξ.3c) 在 水 作用下， 生成 (1S,2S,5S)-5-isopropenyl-2-methyl-3-oxo-cyclohexane-1-carbonitrile
  参考文献：
  名称：

  Abe, Science reports of the Tokyo Bunrika Daigaku, section A. Mathematics, physics, chemistry., 1938, vol. 3, p. 217,221

  摘要：

  DOI：

文献信息

• Dauben–Michno oxidative transposition of allylic cyanohydrins — Enantiomeric switch of (–)-carvone to (+)-carvone*Based on the 2010 Bader Award Lecture.
  作者：Jason R. Hudlicky、Lukas Werner、Vladislav Semak、Razvan Simionescu、Tomas Hudlicky

  DOI：10.1139/v11-026

  日期：2011.5

  Allylic cyanohydrins were subjected to Dauben–Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (–)-carvone to its enantiomer.

  烯丙基氰醇在低温下经过Dauben-Michno氧化反应，可以得到良好至优异产率的β-氰基烯酮。通过将(-)-薄荷醛转化为其对映体来测试这种氧化转位作为含有潜在对称面的烯酮的对映异构体转换的潜力。
• Lagriffoul, Pierre-Henri; Tadros, Ziad; Taillades, Jacques, Journal of the Chemical Society. Perkin transactions II, 1992, # 8, p. 1279 - 1285
  作者：Lagriffoul, Pierre-Henri、Tadros, Ziad、Taillades, Jacques、Commeyras, Auguste

  DOI：——

  日期：——
• S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.
  作者：Anja A. Verstegen-Haaksma、Henk J. Swarts、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)89623-x

  日期：1994.1

  Two conjugate addition/annulation methodologies for S-(+)-carvone are reported. The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketones, gave decalones 2a-d stereoselectively and in good yield. The conjugate addition of cyanide anion followed by base catalyzed Robinson annulation with MVK and dehydration gave decalone 2e stereoselectively in very high yield.
• Bousquet, C.; Tadros, Z.; Tonnel, J., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 513 - 520
  作者：Bousquet, C.、Tadros, Z.、Tonnel, J.、Mion, J.、Taillades, J.

  DOI：——

  日期：——
• Abe, Science reports of the Tokyo Bunrika Daigaku, section A. Mathematics, physics, chemistry, 1938, vol. <A> 3, p. 217,229
  作者：Abe

  DOI：——

  日期：——