(6S,7S)=bis(tert-butyldimethylsilyloxy)-9-phenylnon-1-en-8-yne | 306287-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6S,7S)=bis(tert-butyldimethylsilyloxy)-9-phenylnon-1-en-8-yne
• 英文别名: tert-butyl-[(3S,4S)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylnon-8-en-1-yn-4-yl]oxy-dimethylsilane
• CAS: 306287-22-9
• 化学式: C₂₇H₄₆O₂Si₂
• 分子量: 458.832
• InChiKey: KAWINWURSGAHEW-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6S,7S)=bis(tert-butyldimethylsilyloxy)-9-phenylnon-1-en-8-yne 、 alkaline earth salt of/the/ methylsulfuric acid 在 环己胺 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 1.25h， 生成 (2S,3S,6S,7S)-bis(tert-butyldimethylsiloxy)-7-methyl-9-phenylbicyclo[4.3.0]non-1(9)-en-8-one 、 (2S,3S,6S,7R)-bis(tert-butyldimethylsiloxy)-7-methyl-9-phenylbicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  Pauson−Khand Reaction of Optically Active 6,7-Bis(tert-butyldimethylsiloxy)non-1-en-8-ynes

  摘要：

  Treatment of(6S, 7S)-7-bis(tert-butyldimethylsiloxy)non-1-en-8-ynes with dicobalt octacarbonyl gave the corresponding cobalt complex. This complex was subsequently exposed to the Pauson-Khand conditions in the presence of a promoter such as cyclohexylamine, thioanisole, methyl isopropyl sulfide, and butyl methyl sulfide ending up with the stereoselective production of the (2S, 3S, 6S, 7S)-7-methylbicyclo[4.3.0]nonenone derivatives instead of the expected (2S, 3S, 7S)-bicyclo[5.3.0]decenone species.

  DOI：

  10.1021/jo0008082
• 作为产物：
  描述：

  tert-Butyl-((4S,5S)-2,2-dimethyl-5-pent-4-enyl-[1,3]dioxolan-4-ylmethoxy)-dimethyl-silane 在 咪唑 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (6S,7S)=bis(tert-butyldimethylsilyloxy)-9-phenylnon-1-en-8-yne 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Pauson−Khand Reaction of Optically Active 6,7-Bis(tert-butyldimethylsiloxy)non-1-en-8-ynes

  摘要：

  Treatment of(6S, 7S)-7-bis(tert-butyldimethylsiloxy)non-1-en-8-ynes with dicobalt octacarbonyl gave the corresponding cobalt complex. This complex was subsequently exposed to the Pauson-Khand conditions in the presence of a promoter such as cyclohexylamine, thioanisole, methyl isopropyl sulfide, and butyl methyl sulfide ending up with the stereoselective production of the (2S, 3S, 6S, 7S)-7-methylbicyclo[4.3.0]nonenone derivatives instead of the expected (2S, 3S, 7S)-bicyclo[5.3.0]decenone species.

  DOI：

  10.1021/jo0008082

文献信息

• Pauson−Khand Reaction of Optically Active 6,7-Bis(<i>tert</i>-butyldimethylsiloxy)non-1-en-8-ynes
  作者：Chisato Mukai、Hiroshi Sonobe、Jin Sung Kim、Miyoji Hanaoka

  DOI：10.1021/jo0008082

  日期：2000.10.1

  Treatment of(6S, 7S)-7-bis(tert-butyldimethylsiloxy)non-1-en-8-ynes with dicobalt octacarbonyl gave the corresponding cobalt complex. This complex was subsequently exposed to the Pauson-Khand conditions in the presence of a promoter such as cyclohexylamine, thioanisole, methyl isopropyl sulfide, and butyl methyl sulfide ending up with the stereoselective production of the (2S, 3S, 6S, 7S)-7-methylbicyclo[4.3.0]nonenone derivatives instead of the expected (2S, 3S, 7S)-bicyclo[5.3.0]decenone species.