(Z)-6-(triethylsilyl)hex-5-en-2-one | 1214320-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-6-(triethylsilyl)hex-5-en-2-one
• 英文别名: (Z)-6-triethylsilylhex-5-en-2-one
• CAS: 1214320-47-4
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: JUASCNVBVDKMAQ-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 5-已烯-2-酮 在 降冰片烯 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62%的产率得到(Z)-6-(triethylsilyl)hex-5-en-2-one
  参考文献：
  名称：

  Iridium-Catalyzed (Z)-Trialkylsilylation of Terminal Olefins

  摘要：

  A complex of commercial [Ir(OMe)(cod)](2) and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 degrees C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and sillanes. alpha,beta-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.

  DOI：

  10.1021/jo902678p

文献信息

• Iridium-Catalyzed (<i>Z</i>)-Trialkylsilylation of Terminal Olefins
  作者：Biao Lu、J. R. Falck

  DOI：10.1021/jo902678p

  日期：2010.3.5

  A complex of commercial [Ir(OMe)(cod)](2) and 4,4-di-tert-butyl-2,2-bipyridine (dtbpy) catalyzes the Z-selective, dehydrative silylation of terminal alkenes, but not 1,2-disubstituted alkenes, with triethylsilane or benzyldimethylsilane in THF at 40 degrees C. Yields and Z-stereoselectivity were significantly improved by 2-norbornene, in contrast with other sacrificial alkenes. The reaction is compatible with many functional groups including epoxides, ketones, amides, alcohols, esters, halides, ketals, and sillanes. alpha,beta-Unsaturated esters were unreactive. The reaction probably proceeds through a Heck-type mechanism.