(E)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-8-trimethylsilanyl-oct-2-en-7-ynoic acid ethyl ester | 284034-58-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-8-trimethylsilanyl-oct-2-en-7-ynoic acid ethyl ester
• 英文别名: ethyl (E)-6-[tert-butyl(dimethyl)silyl]oxy-5,5-dimethyl-8-trimethylsilyloct-2-en-7-ynoate
• CAS: 284034-58-8
• 化学式: C₂₁H₄₀O₃Si₂
• 分子量: 396.718
• InChiKey: SWMSLMLTMILJIB-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-8-trimethylsilanyl-oct-2-en-7-ynoic acid ethyl ester 在 dicobalt octacarbonyl 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以92%的产率得到(E)-3-[(1S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-2-trimethylsilanyl-cyclopent-2-enyl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Diastereoselective Formation of 5-Vinylcyclopentenes from 1,6-Enynes:  Cobalt-Mediated C−H Allylic Activation and Formal 5-Endo-Dig Cyclization

  摘要：

  [GRAPHICS]A novel intramolecular cyclization reaction mediated by dicobalt octacarbonyl (Co-2(CO)(8)) is reported. Thermolysis in an argon atmosphere transforms the cobalt complex of 1-trimethyisilyl-6-hepten-1-ynes into 1-trimethylsilyl-5-vinylcyclopentenes in good yield and in a highly diastereoselective manner. This formal 5-endo-dig cyclization is proposed to proceed via an allylic C-H oxidative addition.

  DOI：

  10.1021/ol005928a
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-1-trimethylsilyl-hept-6-en-1-yne 在 四氧化锇 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 21.5h， 生成 (E)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-8-trimethylsilanyl-oct-2-en-7-ynoic acid ethyl ester
  参考文献：
  名称：

  Diastereoselective Formation of 5-Vinylcyclopentenes from 1,6-Enynes:  Cobalt-Mediated C−H Allylic Activation and Formal 5-Endo-Dig Cyclization

  摘要：

  [GRAPHICS]A novel intramolecular cyclization reaction mediated by dicobalt octacarbonyl (Co-2(CO)(8)) is reported. Thermolysis in an argon atmosphere transforms the cobalt complex of 1-trimethyisilyl-6-hepten-1-ynes into 1-trimethylsilyl-5-vinylcyclopentenes in good yield and in a highly diastereoselective manner. This formal 5-endo-dig cyclization is proposed to proceed via an allylic C-H oxidative addition.

  DOI：

  10.1021/ol005928a

文献信息

• Diastereoselective Formation of 5-Vinylcyclopentenes from 1,6-Enynes:  Cobalt-Mediated C−H Allylic Activation and Formal 5-Endo-Dig Cyclization
  作者：Régis Dolaine、James L. Gleason

  DOI：10.1021/ol005928a

  日期：2000.6.1

  [GRAPHICS]A novel intramolecular cyclization reaction mediated by dicobalt octacarbonyl (Co-2(CO)(8)) is reported. Thermolysis in an argon atmosphere transforms the cobalt complex of 1-trimethyisilyl-6-hepten-1-ynes into 1-trimethylsilyl-5-vinylcyclopentenes in good yield and in a highly diastereoselective manner. This formal 5-endo-dig cyclization is proposed to proceed via an allylic C-H oxidative addition.