1-(4-chlorophenyl)-2,2-difluoroethan-1-ol

• 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-(4-chlorophenyl)-2,2-difluoroethan-1-ol
• 英文别名: 1-(4-Chlorophenyl)-2,2-difluoroethanol
• 化学式: C₈H₇ClF₂O
• 分子量: 192.593
• InChiKey: JGZVFDXSUANZDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethan-1-ol 在 sodium acetate 、 magnesium 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到1-(4-chlorophenyl)-2,2-difluoroethan-1-ol
  参考文献：
  名称：

  Nucleophilic difluoromethylation of carbonyl compounds using TMSCF2SO2Ph and Mg0-mediated desulfonylation

  摘要：

  A new nucleophilic difluoromethylation chemistry using fluoride-induced (phenylsulfonyl)difluoromethylation with TMSCF2SO2Ph followed by the magnesium-metal-mediated desulfonylation has been achieved. This methodology is compatible with both enolizable and non-enolizable aldehydes and ketones and has special advantage in the case of enolizable aldehydes. The new efficient desulfonylation method is considered to be environmentally benign due to the absence of mercury. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.162

文献信息

• Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF₂H
  作者：Guang-Fen Du、Ying Wang、Cheng-Zhi Gu、Bin Dai、Lin He

  DOI：10.1039/c5ra04472c

  日期：——

  Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF₂H.

  有机催化剂直接用TMSCF2H对醛和酮进行二氟甲基化。
• Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate
  作者：Petr Beier、Anastasia V. Alexandrova、Mikhail Zibinsky、G.K. Surya Prakash

  DOI：10.1016/j.tet.2008.10.006

  日期：2008.12

  New methodology for difluoromethylation and difluoromethylenation of aldehydes and ketones based on nucleophilic fluorination using diethyl difluoromethylphosphonate (1) was developed.

  开发了基于使用二氟甲基膦酸二乙酯 (1) 进行亲核氟化的醛和酮的二氟甲基化和二氟甲基化的新方法。
• Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl(trifluoromethyl)silane (TMSCF 3 )
  作者：Sankarganesh Krishnamoorthy、Sayan Kar、Jotheeswari Kothandaraman、G.K. Surya Prakash

  DOI：10.1016/j.jfluchem.2018.01.009

  日期：2018.4

  Reaction of the Ruppert–Prakash reagent (Me3SiCF3) with aromatic aldehydes in the presence of triphenylphosphine, lithium iodide and lithium tetrafluoroborate selectively furnishes gem-difluorinated phosphonium salts. Simple alkaline hydrolysis of these salts results in difluoromethylated products. Thus, one-pot nucleophilic difluoromethylation of aromatic aldehydes using Me3SiCF3 has been accomplished

  在三苯基膦，碘化锂和四氟硼酸锂的存在下，Ruppert-Prakash试剂（Me 3 SiCF 3）与芳族醛的反应选择性地提供了宝石二氟化phospho盐。这些盐的简单碱性水解产生二氟甲基化产物。因此，已经实现了使用Me 3 SiCF 3一锅法芳香族醛的亲核二氟甲基化。该方案容许吸电子以及给电子取代基。
• Facile Preparation of Fluorine-containing Alkenes, Amides and Alcohols <i>via</i> the Electrophilic Fluorination of Alkenyl Boronic Acids and Trifluoroborates
  作者：Nicos Petasis、Andrei Yudin、Ilia Zavialov、G. Prakash、George Olah

  DOI：10.1055/s-1997-3228

  日期：1997.5

  Reaction of alkenyl boronic acids, or preferably alkenyl trifluoroborates, with one equivalent of SelectfluorTM gives the corresponding alkenyl fluorides. A similar reaction with two equivalents of SelectfluorTM in water or a nitrile solvent gives difluoromethyl-substituted alcohols and amides respectively.

  烯基硼酸（或更优选的烯基三氟硼酸盐）与一当量的Selectfluor™反应，生成相应的烯基氟化物。与两当量的Selectfluor™在水或氰类溶剂中进行类似反应，分别生成二氟甲基取代的醇和酰胺。
• Trapping of Difluorocarbene by Frustrated Lewis Pairs
  作者：Vladimir O. Smirnov、Alexander D. Volodin、Alexander A. Korlyukov、Alexander D. Dilman

  DOI：10.1002/anie.202001354

  日期：2020.7.20

  Frustrated Lewis pairs consisting of diphenylphosphino and boryl groups located at the ortho‐position can trap difluorocarbene affording stable zwitterionic adducts. The reaction can be reversed to release difluorocarbene at elevated temperatures.

  由位于邻位的二苯基膦基和硼基组成的沮丧的Lewis对可以捕获二氟卡宾，提供稳定的两性离子加合物。该反应可以在升高的温度下逆转以释放出二氟卡宾。