2-(4-benzonitrile)-1,1,1-trifluorobutan-2-ol | 1050445-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-benzonitrile)-1,1,1-trifluorobutan-2-ol
• 英文别名: 4-(1,1,1-Trifluoro-2-hydroxybutan-2-yl)benzonitrile；4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)benzonitrile
• CAS: 1050445-57-2
• 化学式: C₁₁H₁₀F₃NO
• 分子量: 229.202
• InChiKey: ITDFEVAAXSTYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(三氟乙酰基)苯甲腈 、 diethylzinc 在 (S,S)-(-)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 作用下， 以 正己烷 、 甲苯 为溶剂， 以71%的产率得到2-(4-benzonitrile)-1,1,1-trifluorobutan-2-ol
  参考文献：
  名称：

  Catalytic Enantioselective Addition of Diethylzinc to Trifluoromethyl Ketones

  摘要：

  A procedure for nucleophilic addition of diethylzinc to trifluoromethyl ketones was developed. The TMEDA-catalyzed method converts aromatic substrates to the corresponding 2-aryl-1,1,1-trifluorobutan-2-ols in up to 99% yield, and it is also applicable to less reactive aliphatic ketones if stoichiometric ligand amounts are employed. The first asymmetric variant producing tertiary alcohols with up to 61% ee when TBOX is used as catalyst is described.

  DOI：

  10.1021/ol8015012

文献信息

• Catalytic Enantioselective Addition of Diethylzinc to Trifluoromethyl Ketones
  作者：Kimberly Yearick、Christian Wolf

  DOI：10.1021/ol8015012

  日期：2008.9.1

  A procedure for nucleophilic addition of diethylzinc to trifluoromethyl ketones was developed. The TMEDA-catalyzed method converts aromatic substrates to the corresponding 2-aryl-1,1,1-trifluorobutan-2-ols in up to 99% yield, and it is also applicable to less reactive aliphatic ketones if stoichiometric ligand amounts are employed. The first asymmetric variant producing tertiary alcohols with up to 61% ee when TBOX is used as catalyst is described.