((3Z,5E)-3-Hexyl-deca-3,5-dien-1-ynyl)-trimethyl-silane | 798553-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3Z,5E)-3-Hexyl-deca-3,5-dien-1-ynyl)-trimethyl-silane
• CAS: 798553-62-5
• 化学式: C₁₉H₃₄Si
• 分子量: 290.564
• InChiKey: AQNFZOYBQQOGDZ-GAAMGZSTSA-N

物化性质

• 沸点：
  358.9±9.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  ((3Z,5E)-3-Hexyl-deca-3,5-dien-1-ynyl)-trimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (5E,7Z)-8-Ethynyl-tetradeca-5,7-diene
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides

  摘要：

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.

  DOI：

  10.1021/jo048983w
• 作为产物：
  描述：

  (Z)-3-Iodo-2-nonen-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 二乙胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ((3Z,5E)-3-Hexyl-deca-3,5-dien-1-ynyl)-trimethyl-silane
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclization of Alkyne−Epoxide Functionalities through Alternation of the Substituent and Structural Skeleton of Epoxides

  摘要：

  Treatment of 1-(o-ethynylphenyl)-2-alkyl-2-aryl epoxides with TpRuPPh(3)(CH3CN)(2)PF6 catalyst (10 mol %) in hot toluene (100 degreesC, 12 h) led to an atypical cyclization and gave 1-aryl-2-alkyl-1H-indene derivatives and carbon monoxide efficiently. The cyclization of 1-cis-enynyl-2-alkyl epoxides with this catalyst in hot toluene (10 mol %, 100 degreesC, 12 h) gave 2,5-disubstituted phenols in 45-72% yields. Under the same conditions, 1-cis-enynyl-2,2-dialkyl epoxides and 1-cis-enynyl-2-alkyl-2-aryl epoxides gave the corresponding 6,6-disubstituted cyclohexa-2,4-dien-1-ones in good yields (85-91%). Mechanisms for these new cyclization reactions are proposed on the basis of trapping experiments and isotope labeling experiments. The formation of 1H-indene products likely involves ruthenium-acyl intermediates whereas cyclohexa-2,4-dien-1-ones are thought to derive from ruthenium-ketene intermediates.

  DOI：

  10.1021/jo048983w