4-((S)-1,4-Dimethyl-7-triethylsilanyloxy-cyclohept-3-enyl)-butyronitrile | 461663-57-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-((S)-1,4-Dimethyl-7-triethylsilanyloxy-cyclohept-3-enyl)-butyronitrile
• CAS: 461663-57-0
• 化学式: C₁₉H₃₅NOSi
• 分子量: 321.579
• InChiKey: JYWPPWPKTBZIEG-GGYWPGCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-((S)-1,4-Dimethyl-7-triethylsilanyloxy-cyclohept-3-enyl)-butyronitrile 在 jones reagent 作用下， 以 丙酮 为溶剂， 以1.96 g的产率得到(1S)-4-(1,4-dimethyl-7-oxocyclohept-3-enyl)butanecarbonitrile
  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：

  ethyl 2-allyl-2,6-dimethyl-3-hydroxy-6-heptenoate 在 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum 吡啶 、 咪唑 、 氢氧化钾 、 lithium aluminium tetrahydride 、 jones reagent 、 18-冠醚-6 、 (S)-(-)- α-甲基苄胺 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 149.5h， 生成 4-((S)-1,4-Dimethyl-7-triethylsilanyloxy-cyclohept-3-enyl)-butyronitrile
  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