(3aS,5aR,8bS)-2,2-Di-tert-butyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one | 216103-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,5aR,8bS)-2,2-Di-tert-butyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one
• 英文别名: (3aS,5aR,8bS)-2,2-ditert-butyl-3a,4,5,5a,6,8b-hexahydroindeno[4,5-d][1,3,2]dioxasilol-7-one
• CAS: 216103-14-9
• 化学式: C₁₇H₂₈O₃Si
• 分子量: 308.493
• InChiKey: GGDSOKXPVKZVCD-UGFHNGPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,5aR,8bS)-2,2-Di-tert-butyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one 在 四丁基氟化铵 作用下， 生成 (2S,3S,6R)-2,3-dihydroxybicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  Diastereocomplementary construction of optically active bicyclo[4.3.0]nonenone skeleton based on Pauson-Khand reaction

  摘要：

  The Pauson-Khand reaction of the (3S,4S)-3,4-bis(tert-butyldimethylsilyloxy)-7-octene-1-yne derivatives, derived from (+)-diethyl tartrate, exclusively gave the (2S,3S,6S)-2,3-bis(tert-butyldimethylsilyloxy)bicyclo[4.3.0]non-derivatives, while the (3S,4S)-3,4-dihydroxy-7-octen-1-yne congeners diastereocomplementarily afforded the corresponding (2S,3S,6R)-2,3-dihydroxy-bicyclo[4.3.0]non-1(9)-en-8-one in a highly selective manner. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01754-7
• 作为产物：
  描述：

  (5S,6S)-5,6-bis(tert-butyldimethylsilylenedioxy)oct-1-en-7-yne 、 alkaline earth salt of/the/ methylsulfuric acid 在 十二/十四烷基二甲基氧化胺 作用下， 生成 (3aS,5aR,8bS)-2,2-Di-tert-butyl-3a,4,5,5a,6,8b-hexahydro-1,3-dioxa-2-sila-as-indacen-7-one
  参考文献：
  名称：

  Diastereocomplementary construction of optically active bicyclo[4.3.0]nonenone skeleton based on Pauson-Khand reaction

  摘要：

  The Pauson-Khand reaction of the (3S,4S)-3,4-bis(tert-butyldimethylsilyloxy)-7-octene-1-yne derivatives, derived from (+)-diethyl tartrate, exclusively gave the (2S,3S,6S)-2,3-bis(tert-butyldimethylsilyloxy)bicyclo[4.3.0]non-derivatives, while the (3S,4S)-3,4-dihydroxy-7-octen-1-yne congeners diastereocomplementarily afforded the corresponding (2S,3S,6R)-2,3-dihydroxy-bicyclo[4.3.0]non-1(9)-en-8-one in a highly selective manner. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01754-7

文献信息

• Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives
  作者：Chisato Mukai、Jin Sung Kim、Hiroshi Sonobe、Miyoji Hanaoka

  DOI：10.1021/jo990819z

  日期：1999.9.1

  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.