N,N-dicyclohexyltrifluoromethanesulfenamide

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: N,N-dicyclohexyltrifluoromethanesulfenamide
• 英文别名: N-cyclohexyl-N-[(trifluoromethyl)sulfanyl]cyclohexanamine；N-cyclohexyl-N-(trifluoromethylsulfanyl)cyclohexanamine
• 化学式: C₁₃H₂₂F₃NS
• 分子量: 281.386
• InChiKey: CIBKBFLYWOOGLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dicyclohexyltrifluoromethanesulfenamide 、 N,N-dichlorotrifluoromethylsulfonamide 以 二氯甲烷 为溶剂， 以51%的产率得到N,N-dicyclohexyl-N'-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamide
  参考文献：
  名称：

  Unusual reactions of N-(trifluoromethylsulfonylimino)di-and-trifluoromethanesulfinimidoyl chlorides

  摘要：

  N-(Trifluoromethylsulfonylimino)di- and -trifluoromethanesulfinimidoyl chlorides RS(=NSO2CF3)Cl (R = CF3, CHF2) react with potassium fluoride in 1,2-dimethoxyethane with formation of the corresponding N,N'-bis(trifluoromethylsulfonyl)fluoromethanesulfinimidamide potassium salts RS(=NSO2CF3)NSO2CF3-K+. Analogous methanesulfinimidoyl and fluoromethanesulfinimidoyl chlorides (R = CH3, CH2F) fail to react with KF under similar conditions. Treatment of trifluoromethanesulfenamides CF3SNR2 with N,N-dichlorotrifluoro-methanesulfonamide CF3SO2NCl2 leads to N,N-disubstituted N'-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamides CF3S(=NSO2CF3)NR2. The reaction of N,N-dimethyl-N'-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamide (R = CH3) with gaseous hydrogen chloride in diethyl ether gives sulfinimidoyl chloride CF3S(=NSO2CF3)Cl which could not be obtained by imination of CF3SCl.

  DOI：

  10.1134/s1070428006090041
• 作为产物：
  描述：

  N-甲基-N-苯基-S-(三氟甲基)硫代羟胺 、 二环己胺 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以79%的产率得到N,N-dicyclohexyltrifluoromethanesulfenamide
  参考文献：
  名称：

  Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide

  摘要：

  CF₃SN基团是一个具有有趣性质的取代基。然而，目前还没有简便的合成方法来获得带有这个基团的分子。三氟甲硫酰氟化铵是一种新的试剂，用于进行亲电三氟甲硫基化反应，它可以容易地与胺类化合物反应，以良好的产率获得三氟甲硫基胺。

  DOI：

  10.3762/bjoc.9.270

文献信息

• Direct electrophilic <i>N</i>-trifluoromethylthiolation of amines with trifluoromethanesulfenamide
  作者：Sébastien Alazet、Kevin Ollivier、Thierry Billard

  DOI：10.3762/bjoc.9.270

  日期：——

  The CF₃SN moiety is a substituent with interesting properties. However, there is no easy synthetic access to molecules bearing this group. The trifluoromethanesulfenamide is a new reagent for the electrophilic trifluoromethylthiolation which reacts easily with amines to obtain trifluoromethylsulfanylamines with good yields.

  CF₃SN基团是一个具有有趣性质的取代基。然而，目前还没有简便的合成方法来获得带有这个基团的分子。三氟甲硫酰氟化铵是一种新的试剂，用于进行亲电三氟甲硫基化反应，它可以容易地与胺类化合物反应，以良好的产率获得三氟甲硫基胺。

• Unusual reactions of N-(trifluoromethylsulfonylimino)di-and-trifluoromethanesulfinimidoyl chlorides
  作者：L. M. Yagupol’skii、A. V. Bezdudnyi、Yu. L. Yagupol’skii

  DOI：10.1134/s1070428006090041

  日期：2006.9

  N-(Trifluoromethylsulfonylimino)di- and -trifluoromethanesulfinimidoyl chlorides RS(=NSO2CF3)Cl (R = CF3, CHF2) react with potassium fluoride in 1,2-dimethoxyethane with formation of the corresponding N,N'-bis(trifluoromethylsulfonyl)fluoromethanesulfinimidamide potassium salts RS(=NSO2CF3)NSO2CF3-K+. Analogous methanesulfinimidoyl and fluoromethanesulfinimidoyl chlorides (R = CH3, CH2F) fail to react with KF under similar conditions. Treatment of trifluoromethanesulfenamides CF3SNR2 with N,N-dichlorotrifluoro-methanesulfonamide CF3SO2NCl2 leads to N,N-disubstituted N'-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamides CF3S(=NSO2CF3)NR2. The reaction of N,N-dimethyl-N'-(trifluoromethylsulfonyl)trifluoromethanesulfinimidamide (R = CH3) with gaseous hydrogen chloride in diethyl ether gives sulfinimidoyl chloride CF3S(=NSO2CF3)Cl which could not be obtained by imination of CF3SCl.