1-(2-bromophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethanol | 1460342-58-8

• 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-(2-bromophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethanol
• 英文别名: 2-(Benzenesulfonyl)-1-(2-bromophenyl)-2,2-difluoroethanol；2-(benzenesulfonyl)-1-(2-bromophenyl)-2,2-difluoroethanol
• CAS: 1460342-58-8
• 化学式: C₁₄H₁₁BrF₂O₃S
• 分子量: 377.206
• InChiKey: XRTIZGWFJLEUGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-(2-bromophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethanol
  参考文献：
  名称：

  Nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls with PhSO2CF2H reagent in the presence of in situ generated substoichiometric amount of base

  摘要：

  The reactions between carbonyl compounds and PhSO2CF2H using substoichiometric amount of base in situ generated from N(TMS)(3) and catalytic amount of Me4NF have been investigated. It is found that both enolizable and non-enolizable aldehydes are suitable substrates to undergo nucleophilic difluoro(phenylsulfonyl)methylation. Compared to the previously reported trifluoromethylation of carbonyls with CF3H under the similar reaction conditions, the unique reactivity of PhSO2CF2H is attributed to its higher acidity than CF3H and the reversibility of its addition reaction with ketones under basic conditions. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.05.015

文献信息

• Nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls with PhSO2CF2H reagent in the presence of in situ generated substoichiometric amount of base
  作者：Mingyou Hu、Bing Gao、Chuanfa Ni、Laijun Zhang、Jinbo Hu

  DOI：10.1016/j.jfluchem.2013.05.015

  日期：2013.11

  The reactions between carbonyl compounds and PhSO2CF2H using substoichiometric amount of base in situ generated from N(TMS)(3) and catalytic amount of Me4NF have been investigated. It is found that both enolizable and non-enolizable aldehydes are suitable substrates to undergo nucleophilic difluoro(phenylsulfonyl)methylation. Compared to the previously reported trifluoromethylation of carbonyls with CF3H under the similar reaction conditions, the unique reactivity of PhSO2CF2H is attributed to its higher acidity than CF3H and the reversibility of its addition reaction with ketones under basic conditions. (C) 2013 Elsevier B.V. All rights reserved.