(3aR,4R,7S,7aR)-4,7-difluoro-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole | 1063610-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,7S,7aR)-4,7-difluoro-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole
• CAS: 1063610-90-1
• 化学式: C₉H₁₂F₂O₂
• 分子量: 190.19
• InChiKey: GGQINVBSRSXQHH-YWIQKCBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7S,7aR)-4,7-difluoro-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 、 sodium sulfite 作用下， 以 丙酮 为溶剂， 反应 240.25h， 以59%的产率得到(3aR,4R,5S,6R,7S,7aR)-4,7-difluoro-2,2-dimethylhexahydro-1,3-benzodioxole-5,6-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
• 作为产物：
  描述：

  (4R,5R)-4-[1-fluoroprop-2-en-1-yl]-5-[(1S)-fluoroprop-2-en-1-yl]-2,2-dimethyl-1,3-dioxolane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以53%的产率得到(3aR,4R,7S,7aR)-4,7-difluoro-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole
  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