2,5-bis(trifluoromethyl)hexane-2,5-diol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(trifluoromethyl)hexane-2,5-diol
• 英文别名: 1,1,1,6,6,6-Hexafluoro-2,5-dimethylhexane-2,5-diol
• 化学式: C₈H₁₂F₆O₂
• 分子量: 254.172
• InChiKey: QHGNOXDDLDFIGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,1,1,6,6,6-Hexafluoro-2,5-dimethyl-2,5-bis-trimethylsilanyloxy-hexane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到2,5-bis(trifluoromethyl)hexane-2,5-diol
  参考文献：
  名称：

  Diketo Compounds with (Trifluoromethyl)trimethylsilane:  Double Nucleophilic Trifluoromethylation Reactions

  摘要：

  Reactions of various diketo compounds with (trifluoromethyl)trimethylsilane (Me3SiCF3) in the presence of catalytic amounts of cesium fluoride have been studied. gamma -Ketoesters, CH3COCH2CH2CH2R (R = Et, Bu), were reacted with 2 equiv of Me3SiCF3 at room temperature to give CH3C(OH)(CF3)CH2CH2COCF3 in good yield after hydrolysis. alpha -Diketones, R1COCOR2 (R-1 = R-2 = Ph; R-1 = Ph, R-2 = Me; R-1 = R-2 = Me; R-1 = Me, R-2 = Et), when reacted with Me3SiCF3, formed 1:1 or 1:2 addition products depending on the reaction conditions and stoichiometry used. Reactions of diones CH3COXCOCH3 (X = -CH2CH2-, -C6H4C6H4-, -CH2-) with Me3SiCF3 also led to the formation of the mono- or diaddition products depending on reaction conditions. With various kinds of substituted arylglyoxals, 2 equiv of Me3SiCF3 produced monoaddition products in 70-75% yield and diaddition products in 5-10% yield. One of the monoalcohols and two of the diols have been characterized by single-crystal X-ray analysis, and the presence of inter- and intramolecular hydrogen bonding has been confirmed.

  DOI：

  10.1021/jo0057304

文献信息

• Diketo Compounds with (Trifluoromethyl)trimethylsilane:  Double Nucleophilic Trifluoromethylation Reactions
  作者：Rajendra P. Singh、Jeffry M. Leitch、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/jo0057304

  日期：2001.2.1

  Reactions of various diketo compounds with (trifluoromethyl)trimethylsilane (Me3SiCF3) in the presence of catalytic amounts of cesium fluoride have been studied. gamma -Ketoesters, CH3COCH2CH2CH2R (R = Et, Bu), were reacted with 2 equiv of Me3SiCF3 at room temperature to give CH3C(OH)(CF3)CH2CH2COCF3 in good yield after hydrolysis. alpha -Diketones, R1COCOR2 (R-1 = R-2 = Ph; R-1 = Ph, R-2 = Me; R-1 = R-2 = Me; R-1 = Me, R-2 = Et), when reacted with Me3SiCF3, formed 1:1 or 1:2 addition products depending on the reaction conditions and stoichiometry used. Reactions of diones CH3COXCOCH3 (X = -CH2CH2-, -C6H4C6H4-, -CH2-) with Me3SiCF3 also led to the formation of the mono- or diaddition products depending on reaction conditions. With various kinds of substituted arylglyoxals, 2 equiv of Me3SiCF3 produced monoaddition products in 70-75% yield and diaddition products in 5-10% yield. One of the monoalcohols and two of the diols have been characterized by single-crystal X-ray analysis, and the presence of inter- and intramolecular hydrogen bonding has been confirmed.