(1S,7S,8S)-8-cyano-1,4-dimethylbicyclo[5.3.0]dec-3-ene | 461663-42-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,7S,8S)-8-cyano-1,4-dimethylbicyclo[5.3.0]dec-3-ene
• 英文别名: (1S,3aS,8aS)-3a,6-dimethyl-2,3,4,7,8,8a-hexahydro-1H-azulene-1-carbonitrile
• CAS: 461663-42-3
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: SQDFANCIIXFJRI-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,7S,8S)-8-cyano-1,4-dimethylbicyclo[5.3.0]dec-3-ene 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 (1S,3R,4S,7S,8R)-8-acetyl-3,4-epoxy-1,4-dimethylbicyclo[5.3.0]decane
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d
• 作为产物：
  描述：

  3-[(1S)-1,4-dimethyl-7-triethylsilyloxycyclohept-3-en-1-yl]propyl 4-methylbenzenesulfonate 在 吡啶 、 氯化亚砜 、 jones reagent 、 18-冠醚-6 、 potassium tert-butylate 、 magnesium 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 (1S,7S,8S)-8-cyano-1,4-dimethylbicyclo[5.3.0]dec-3-ene
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d

文献信息

• Preparation of Seven-Membered Carbocycles Using Ring-Closing Metathesis Reaction and Application to Syntheses of Tormesol and Cyathane Skeleton
  作者：Katsuyuki Nakashima、Norihiro Fujisaki、Kosuke Inoue、Atsushi Minami、Chisako Nagaya、Masakazu Sono、Motoo Tori

  DOI：10.1246/bcsj.79.1955

  日期：2006.12

  Various precursors were synthesized and were reacted with the Grubbs reagent as well as the second generation Grubbs reagent to cyclize them into seven-membered carbocycles with di- or tri-substituted double bonds. These reactions were used to synthesize (−)-tormesol, which is an enantiomer of sphenolobane-type diterpene that was isolated from Halimium viscosum, and a basic skeleton of cyathane-type diterpene.

  我们合成了各种前体，并用格拉布斯试剂和第二代格拉布斯试剂将它们环化成具有二或三取代双键的七元碳环。利用这些反应合成了 (-)-tormesol （一种从 Halimium viscosum 分离出来的 sphenolobane 型二萜的对映体）和一种 cyathane 型二萜的基本骨架。
• Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)<i>E</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)<i>Z</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond
  作者：Katsuyuki Nakashima、Kosuke Inoue、Masakazu Sono、Motoo Tori

  DOI：10.1021/jo020287d

  日期：2002.8.1

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.