(2E,4S,5S,6E)-1,8-bis(trimethylsilyl)octa-2,6-diene-4,5-diol | 1063610-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E,4S,5S,6E)-1,8-bis(trimethylsilyl)octa-2,6-diene-4,5-diol
• CAS: 1063610-83-2
• 化学式: C₁₄H₃₀O₂Si₂
• 分子量: 286.562
• InChiKey: FEFOJKGXOHQTSH-FETIZUMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2E,4S,5S,6E)-1,8-bis(trimethylsilyl)octa-2,6-diene-4,5-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 [[(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di-prop-1-ene-1,3-diyl]bis(trimethylsilane) 、 [[(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di-(1E)-prop-1-ene-1,3-diyl]bis(trimethylsilane)
  参考文献：
  名称：

  A Two-Directional Approach to Enantiopure 1,4-Difluoro-cyclohexenes: Synthesis of Difluorinated Cyclitol Analogues

  摘要：

  Enantiopure 1,4-difluoro-cyclohexenes were prepared from readily available acetonide-protected (3S,4S)-hexa-1,5-diene-3,4-diol. In a two-directional mode, a double cross-metathesis reaction using allyltrimethylsilane as the olefinic partner, followed by electrophilic fluorination, afforded diastereomeric acetonide-protected 3,6-difluoro-octa-1,7-diene-4,5-diols. These dienes were found to be suitable substrates for ring-closing metathesis, delivering cyclohexenes featuring fluorine atoms on the two allylic positions flanking the double bond. Upon dihydroxylation, novel difluorinated cyclitol analogues were formed.

  DOI：

  10.1021/ol8017402
• 作为产物：
  描述：

  (3S,4S)-hexa-1,5-diene-3,4-diol 、 烯丙基三甲基硅烷 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到(2E,4S,5S,6E)-1,8-bis(trimethylsilyl)octa-2,6-diene-4,5-diol
  参考文献：
  名称：

  A Two-Directional Approach to Enantiopure 1,4-Difluoro-cyclohexenes: Synthesis of Difluorinated Cyclitol Analogues

  摘要：

  Enantiopure 1,4-difluoro-cyclohexenes were prepared from readily available acetonide-protected (3S,4S)-hexa-1,5-diene-3,4-diol. In a two-directional mode, a double cross-metathesis reaction using allyltrimethylsilane as the olefinic partner, followed by electrophilic fluorination, afforded diastereomeric acetonide-protected 3,6-difluoro-octa-1,7-diene-4,5-diols. These dienes were found to be suitable substrates for ring-closing metathesis, delivering cyclohexenes featuring fluorine atoms on the two allylic positions flanking the double bond. Upon dihydroxylation, novel difluorinated cyclitol analogues were formed.

  DOI：

  10.1021/ol8017402