(3S,4S)-oct-7-en-1-yne-3,4-diol | 216102-96-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4S)-oct-7-en-1-yne-3,4-diol
• CAS: 216102-96-4
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: KLQXJKZAGMCJDU-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (3S,4S)-oct-7-en-1-yne-3,4-diol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以99%的产率得到(5S,6S)-5,6-bis(tert-butyldimethylsiloxy)oct-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
• 作为产物：
  描述：

  (2R,3R)-2,3-isopropylidendioxy-6-hepten-1-ol 在 正丁基锂 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 27.17h， 生成 (3S,4S)-oct-7-en-1-yne-3,4-diol
  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

文献信息

• Diastereocomplementary construction of optically active bicyclo[4.3.0]nonenone skeleton based on Pauson-Khand reaction
  作者：Chisato Mukai、Jin Sung Kim、Masahiko Uchiyama、Miyoji Hanaoka

  DOI：10.1016/s0040-4039(98)01754-7

  日期：1998.10

  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.