(4R,5R)-4-[(1R)-1-fluoroprop-2-en-1-yl]-5-[(1S)-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane | 1063610-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-[(1R)-1-fluoroprop-2-en-1-yl]-5-[(1S)-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4R,5R)-5-[(1S)-1-fluoroprop-2-enyl]-4-[(1R)-1-fluoroprop-2-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1063610-86-5
• 化学式: C₁₁H₁₆F₂O₂
• 分子量: 218.244
• InChiKey: QJHGWDQHNNKHFJ-JXUBOQSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [[(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di-prop-1-ene-1,3-diyl]bis(trimethylsilane) 在 碳酸氢钠 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 90.0h， 生成 (4R,5R)-4,5-bis[(1R)-1-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane 、 (4R,5R)-4-[(1R)-1-fluoroprop-2-en-1-yl]-5-[(1S)-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane 、 (4R,5R)-4,5-bis[(1S)-1-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane
  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