(3S,4S)-1,1-dibromo-3,4-(isopropylidenedioxy)nona-1,8-diene | 306287-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-1,1-dibromo-3,4-(isopropylidenedioxy)nona-1,8-diene
• 英文别名: (4S,5S)-4-(2,2-dibromoethenyl)-2,2-dimethyl-5-pent-4-enyl-1,3-dioxolane
• CAS: 306287-16-1
• 化学式: C₁₂H₁₈Br₂O₂
• 分子量: 354.082
• InChiKey: GXWDXXTZGGEEBM-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (3S,4S)-1,1-dibromo-3,4-(isopropylidenedioxy)nona-1,8-diene 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.0h， 生成 (4S,5S)-4-But-1-ynyl-2,2-dimethyl-5-pent-4-enyl-[1,3]dioxolane
  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：

  [(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 在 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 、 copper(I) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.84h， 生成 (3S,4S)-1,1-dibromo-3,4-(isopropylidenedioxy)nona-1,8-diene
  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.