1,1,1-trifluoro-3-phenyl-2-butanol | 167907-23-5

• 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: 1,1,1-trifluoro-3-phenyl-2-butanol
• 英文别名: 1,1,1-trifluoro-3-phenylbutan-2-ol
• CAS: 167907-23-5
• 化学式: C₁₀H₁₁F₃O
• 分子量: 204.192
• InChiKey: VNJIRHGMWKPGOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-3-phenyl-2-butanol 在 Oxone 、 2-碘苯磺酸钠 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 以92%的产率得到1,1,1-trifluoro-3-phenylbutan-2-one
  参考文献：
  名称：

  氟代烷基取代的甲醇衍生物氧化的新条目：有机碘（V）试剂催化氧化的范围和限制

  摘要：

  钠2-碘和过硫酸氢钾的催化量的影响下的各种氟烷基取代甲醇衍生物的氧化®在CH 3 CN或CH 3 NO 2详细进行了研究。通过与其他氧化方法（如Dess-Martin，PDC和Swern氧化方法）进行比较，还评估了新开发的氧化方法的效率。

  DOI：

  10.1016/j.jfluchem.2012.03.002
• 作为产物：
  描述：

  1,1,1-trifluoro-3-phenylbutan-2-one 在 lithium aluminium tetrahydride 作用下， 以84%的产率得到1,1,1-trifluoro-3-phenyl-2-butanol
  参考文献：
  名称：

  1,1,1-Trifluoro-3-phenyl-2-butylp-Nitrobenzoate

  摘要：

  The reduction of the trifluoromethylated ketone, 1,1,1-trifluoro-3-phenyl-2-butanone, (1), or its hydrogenated homologue, 3-phenyl-2-butanone, (2), with lithium aluminium hydride (LAH) gave 1,1,1-trifluoro-3-phenyl-2-butanol, (4), or 3-phenyl-2-butanol, (3), respectively, as a mixture of the (R*R*)/(R*S*) isomers. The title compound, C17H14F3NO4, (5), was obtained by a benzoylation reaction of the major diastereoisomer of (4). The threo-(R*R*) configuration is clearly evidenced in the crystal structure of (5). So, in the reduction of (1) or (2), the three isomer is the major product. It is note-worthy that the presence of the CF3 group enhances the diastereoselectivity of the reduction reaction.

  DOI：

  10.1107/s0108270197008822

文献信息

• Trifluoromethanesulfinamide from Ephedrine: A More Efficient Trifluoro-methylating Reagent
  作者：Thierry Billard、Bernard R. Langlois、Solveig Roussel、Laurent Saint-Jalmes

  DOI：10.1055/s-2004-831322

  日期：——

  Nucleophilic trifluoromethylation of non-enolizable and enolizable carbonyl compounds was achieved with the trifluoromethanesulfinamide derived from O-silylated ephedrine. In contrast to the trifluoroacetamide analog, previously described, this reagent is able to trifluoromethylate more acidic enolizable compounds.

  非烯醇化和烯醇化羰基化合物的亲核三氟甲基化是用衍生自 O-硅烷化麻黄碱的三氟甲亚磺酰胺实现的。与之前描述的三氟乙酰胺类似物相比，该试剂能够使酸性更强的可烯醇化化合物三氟甲基化。
• Mise en évidence d'une réactivité spécifique des trifluorométhylcétones vis-à-vis du bromure d'allylmagnésium
  作者：Caroline Felix、André Laurent、Pierre Mison

  DOI：10.1016/0022-1139(94)03097-j

  日期：1995.1

  report on an unusual reactivity of allylmagnesium bromide. This Grignard reagent acts as a reducing agent towards trifluoromethylated ketones. A single electron transfer is suggested to explain the reductive process. By using an excess of allylmagnesium bromide, an exclusive addition reaction is obtained. The stereochemistry of both addition and reduction reactions is discussed.

  我们希望报告烯丙基溴化镁的异常反应性。该格氏试剂用作三氟甲基化酮的还原剂。建议单次电子转移来解释还原过程。通过使用过量的烯丙基溴化镁，获得排他的加成反应。讨论了加成和还原反应的立体化学。
• A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation
  作者：Yusuke Tanaka、Takashi Ishihara、Tsutomu Konno

  DOI：10.1016/j.jfluchem.2012.03.002

  日期：2012.5

  Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone® in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess–Martin, PDC, and Swern oxidation.

  钠2-碘和过硫酸氢钾的催化量的影响下的各种氟烷基取代甲醇衍生物的氧化®在CH 3 CN或CH 3 NO 2详细进行了研究。通过与其他氧化方法（如Dess-Martin，PDC和Swern氧化方法）进行比较，还评估了新开发的氧化方法的效率。
• 1,1,1-Trifluoro-3-phenyl-2-butyl<i>p</i>-Nitrobenzoate
  作者：R. Faure、C. Félix、A. Laurent、P. Mison

  DOI：10.1107/s0108270197008822

  日期：1997.12.15

  The reduction of the trifluoromethylated ketone, 1,1,1-trifluoro-3-phenyl-2-butanone, (1), or its hydrogenated homologue, 3-phenyl-2-butanone, (2), with lithium aluminium hydride (LAH) gave 1,1,1-trifluoro-3-phenyl-2-butanol, (4), or 3-phenyl-2-butanol, (3), respectively, as a mixture of the (R*R*)/(R*S*) isomers. The title compound, C17H14F3NO4, (5), was obtained by a benzoylation reaction of the major diastereoisomer of (4). The threo-(R*R*) configuration is clearly evidenced in the crystal structure of (5). So, in the reduction of (1) or (2), the three isomer is the major product. It is note-worthy that the presence of the CF3 group enhances the diastereoselectivity of the reduction reaction.