4-methyl-N-[2,2,2-trifluoro-1-(4-chlorophenyl)ethyl]benzenesulfonamide

• 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: 4-methyl-N-[2,2,2-trifluoro-1-(4-chlorophenyl)ethyl]benzenesulfonamide
• 英文别名: N-(1-(4-chlorophenyl)-2,2,2-trifluoroethyl)-4-methylbenzenesulfonamide；N-[1-(4-chlorophenyl)-2,2,2-trifluoroethyl]-4-methylbenzenesulfonamide
• 化学式: C₁₅H₁₃ClF₃NO₂S
• 分子量: 363.788
• InChiKey: KBYDJDQVDFUUFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三氟碘甲烷 、 N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到4-methyl-N-[2,2,2-trifluoro-1-(4-chlorophenyl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  Nucleophilic Trifluoromethylation of Imines Using the CF₃I/TDAE Reagent

  摘要：

  The nucleophilic trifluoromethylation reagent derived from CF3I and tetrakis(dimethylamino)ethylene (TDAE) was found to be effective in addition to both N-tosyl aldimines and N-tolyl sulfinimines, the latter reaction exhibiting very good diastereoselectivity.

  DOI：

  10.1021/jo050483v

文献信息

• Tri-<i>tert</i>-butylphosphine is an Efficient Promoter for the Trifluoromethylation Reactions of Aldehydes, Ketones, Imides and Imines
  作者：Norio Shibata、Takeshi Toru、Satoshi Mizuta、Takayuki Sato、Hiroyuki Fujimoto、Shuichi Nakamura

  DOI：10.1055/s-2006-926223

  日期：——

  A truly catalytic nucleophilic trifluoromethylation reaction of carbonyl compounds with Ruppert’s reagent, Me3SiCF3, has been shown to be efficiently promoted by a P(t-Bu)3-DMF system. Imines were also converted to the desired α-trifluoromethyl amines under similar reaction conditions.

  卡宾结合物与卢普尔特试剂（Me3SiCF3）的真正催化亲核三氟甲基化反应已被证明可通过P(t-Bu)3-DMF系统高效促进。在类似的反应条件下，亚胺也被转化为所需的α-三氟甲基胺。
• Lewis Base-Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)trimethylsilane
  作者：Yoshikazu Kawano、Nobuya Kaneko、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.1133

  日期：2006.7

  Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and aldimines with (perfluoroalkyl)trimethylsilanes (TMSCF3, TMSC2F5, and TMSC3F7) is described. The nitrogen- or oxygen-containing an...

  描述了路易斯碱催化羰基化合物和醛亚胺与（全氟烷基）三甲基硅烷（TMSCF3、TMSC2F5 和 TMSC3F7）的全氟烷基化。含氮或含氧...
• TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane
  作者：Satoru Matsukawa、Marina Saijo

  DOI：10.1016/j.tetlet.2008.05.053

  日期：2008.7

  A highly basic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes trifluoromethylation using trifluoromethyltrimethylsilane to give the corresponding trifluoromethylated products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦，三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三氟甲基三甲基硅烷催化三氟甲基化，以羰基化合物和亚胺的高至高收率得到相应的三氟甲基化产物。
• Organocatalytic trifluoromethylation of imines using phase-transfer catalysis with phenoxides. A general platform for catalytic additions of organosilanes to imines
  作者：Luca Bernardi、Eugenio Indrigo、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1039/c0cc05777k

  日期：——

  A new approach to additions of silicon nucleophiles to imines was developed. The method is based on the phase-transfer of phenoxides by ammonium catalysts, overcoming the inability of amide adducts in promoting the reactions.

  一种新的硅亲核试剂与亚胺加成的方法被开发出来。该方法基于铵催化剂对酚氧化物的相转移，克服了酰胺加成物促进反应的局限性。
• Nucleophilic Trifluoromethylation of <i>N</i>-Tosyl Aldimines
  作者：G. K. Surya Prakash、Mihirbaran Mandal、George A. Olah

  DOI：10.1055/s-2001-9724

  日期：——

  TMSCF3 and tetrabutylammonium (triphenylsilyl) difluorosilicate (TBAT) were used for efficient nucleophilic trifluoromethylation to N-tosyl aldimines. Aromatic, aliphatic and α,β-unsaturated sulfonaldimines were efficiently trifluoromethylated to obtain the corresponding sulfonamide adducts in good to excellent yields.

  TMSCF3 和四丁基（三苯基硅基）二氟硅酸铵（TBAT）被用于高效亲核三氟甲基化 N-对甲基苯磺酰亚胺。芳香族、脂肪族和δ,δ-不饱和磺醛亚胺被有效地三氟甲基化，得到相应的磺酰胺加合物，收率良好至极佳。