(1S,3S,8aR)-3-isopropenyl-8a-methyl-1,2,3,4,6,8,8a-octahydro-6-oxo-1-naphthalenecarbonitrile | 160837-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,8aR)-3-isopropenyl-8a-methyl-1,2,3,4,6,8,8a-octahydro-6-oxo-1-naphthalenecarbonitrile
• 英文别名: 3-Isopropenyl-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-1-naphthalenecarbonitrile；(1S,3S,8aR)-8a-methyl-6-oxo-3-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalene-1-carbonitrile
• CAS: 160837-41-2
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: NDKLWVHUQFDPGB-KYOSRNDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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,3S,8aR)-3-isopropenyl-8a-methyl-1,2,3,4,6,8,8a-octahydro-6-oxo-1-naphthalenecarbonitrile 、 碘甲烷 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 3.5h， 以80%的产率得到(1S,3S,8aR)-3-isopropenyl-1,2,3,5,6,7,8,8a-octahydro-6-oxo-5,5,8a-trimethyl-1-naphthalenecarbonitrile
  参考文献：
  名称：

  从S-（+）-香芹酮全合成drimane倍半萜烯（第5部分）

  摘要：

  将氰化钾共轭添加到S-（+）-香芹酮中，然后用甲基乙烯基酮腈4高环化。然后进行4的甲基化，除去异丙烯基并通过甲酰化引入C-12，从而得到不饱和酮内酯21，它是drimane倍半萜全合成中的极好中间体。这证明与3β-acetoxydrimenin的总合成24。

  DOI：

  10.1016/s0040-4020(01)89624-1
• 作为产物：
  描述：

  (1S,2S,5S)-5-isopropenyl-2-methyl-3-oxo-cyclohexane-1-carbonitrile 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (1S,3S,8aR)-3-isopropenyl-8a-methyl-1,2,3,4,6,8,8a-octahydro-6-oxo-1-naphthalenecarbonitrile
  参考文献：
  名称：

  S-(+)-carvone as starting material in synthesis (part 4). Conjugate addition of cyanide and Grignard nucleophiles followed by annulation to functionalized decalones.

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)89623-x

文献信息

• 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.
• Total synthesis of drimane sesquiterpenes from S-(+)-carvone (part 5)
  作者：Henk J. Swarts、Anja A. Verstegen-Haaksma、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/s0040-4020(01)89624-1

  日期：1994.1

  Conjugate addition of potassium cyanide to S-(+)-carvone followed by annulation with methyl vinyl ketone nitrile 4 in high yield. Methylation of 4, removal of the isopropenyl group and the introduction of C-12 via formylation then gave the unsaturated keto lactone 21 which is an excellent intermediate in the total synthesis of drimane sesquiterpenes. This was demonstrated with the total synthesis of

  将氰化钾共轭添加到S-（+）-香芹酮中，然后用甲基乙烯基酮腈4高环化。然后进行4的甲基化，除去异丙烯基并通过甲酰化引入C-12，从而得到不饱和酮内酯21，它是drimane倍半萜全合成中的极好中间体。这证明与3β-acetoxydrimenin的总合成24。