(5S,6S)-5,6-bis(tert-butyldimethylsilylenedioxy)-8-phenyloct-1-en-7-yne | 249603-85-8

• 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: (5S,6S)-5,6-bis(tert-butyldimethylsilylenedioxy)-8-phenyloct-1-en-7-yne
• 英文别名: (4S,5S)-4-but-3-enyl-2,2-ditert-butyl-5-(2-phenylethynyl)-1,3,2-dioxasilolane
• CAS: 249603-85-8
• 化学式: C₂₂H₃₂O₂Si
• 分子量: 356.58
• InChiKey: MERWBNNFJHQDTH-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  dicobalt octacarbonyl 、 (5S,6S)-5,6-bis(tert-butyldimethylsilylenedioxy)-8-phenyloct-1-en-7-yne 在 dicobalt octacarbonyl 作用下， 以 乙腈 为溶剂， 生成 (3aS,5aS,8bS)-2,2-Di-tert-butyl-8-phenyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one 、 (3aS,5aR,8bS)-2,2-Di-tert-butyl-8-phenyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one
  参考文献：
  名称：

  Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives

  摘要：

  Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co-2(CO)(8) afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimetbylsiloxy)-9-(substituted)bicyclo[4.3.0]non-1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6R)-2,3-dihydroxy-9-(substituted) bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.

  DOI：

  10.1021/jo990819z
• 作为产物：
  描述：

  (2R,3R)-2,3-isopropylidendioxy-6-hepten-1-ol 在 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 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 为溶剂， 反应 34.67h， 生成 (5S,6S)-5,6-bis(tert-butyldimethylsilylenedioxy)-8-phenyloct-1-en-7-yne
  参考文献：
  名称：

  Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives

  摘要：

  Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co-2(CO)(8) afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimetbylsiloxy)-9-(substituted)bicyclo[4.3.0]non-1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6R)-2,3-dihydroxy-9-(substituted) bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.

  DOI：

  10.1021/jo990819z