4-methyl-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfonamide | 235418-61-8

• 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: 4-methyl-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfonamide
• 英文别名: N-(2,2,2-trifluoro-1-phenylethyl)tosylamide；N-tosyl-1-trifluoromethyl-benzylamine
• CAS: 235418-61-8
• 化学式: C₁₅H₁₄F₃NO₂S
• 分子量: 329.343
• InChiKey: MWJPYKVXXYXYJY-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  398.1±52.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 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

• 作为反应物：
  描述：

  4-methyl-N-(2,2,2-trifluoro-1-phenylethyl)benzenesulfonamide 在 氢溴酸 、 苯酚 作用下， 以90%的产率得到
  参考文献：
  名称：

  Nucleophilic Trifluoromethylation of N-Tosyl Aldimines

  摘要：

  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。

  DOI：

  10.1055/s-2001-9724
• 作为产物：
  描述：

  三氟碘甲烷 、 N-tosylbenzaldimine 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到4-methyl-N-(2,2,2-trifluoro-1-phenylethyl)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...
• Synthesis of Organofluorine Compounds Using the Ene Reaction of N-(p-Toluenesulfonyl)trifluoroacetaldehyde Imine.
  作者：Shuichi JONOSHITA、Atsuhiro HARADA、Masaaki OMOTE、Akira ANDO、Itsumaro KUMADAKI

  DOI：10.1248/cpb.47.656

  日期：——

  N-Tosyltrifluoroacetaldehyde imine (4) reacted with terminal olefins by only heating together to give the ene reactin products. This means the imine is much more reactive than trifluoroacetaldehyde (2) itself as an enophile. However, 4 was very sensitive to moisture and the yields were low even if it was used without isolation. Further, it did not react with non-terminal olefins. In the course on study of the mechanism of this reaction, we found that N-(2, 2, 2-trifluoro-1-ethoxyethyl)tosylamide (12), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of titanium(IV) chloride followed by addition of ethanol, reacted in the presence of sodium hydride and titanium(IV) chloride to give the same products from the ene reaction of 4 in much better yields. Interestingly, this reaction proceeded with non-terminal olefins.

  N-Tosyltrifluoroacetaldehyde亚胺（4）仅通过加热即可与末端烯烃反应，生成烯反应产物。这意味着作为亲电试剂，该亚胺比三氟乙醛（2）本身更具反应活性。然而，4对湿气非常敏感，即使不经分离使用，产率也很低。此外，它不与非末端烯烃反应。在研究该反应机理的过程中，我们发现，通过三氟乙醛乙基半缩醛（1）与甲苯磺酰胺（3）在四氯化钛存在下反应，随后加入乙醇得到的N-(2,2,2-三氟-1-乙氧基乙基)甲苯磺酰胺（12），在氢化钠和四氯化钛存在下反应，以更高产率得到与4进行烯反应相同的产物。有趣的是，此反应还能与非末端烯烃进行反应。
• [EN] COMPLEXES FOR NUCLEOPHILIC, RADICAL, AND ELECTROPHILIC POLYFLUOROALKYLATION<br/>[FR] COMPLEXES POUR POLYFLUOROALKYLATION NUCLÉOPHILE, RADICALAIRE ET ÉLECTROPHILE
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2017223406A1

  公开（公告）日：2017-12-28

  Disclosed herein are borazine complexes and use of the same in perfluoroalkylation reactions.

  本文披露了硼氮烷配合物及其在全氟烷基化反应中的应用。
• Borazine‐CF ₃ ⁻ Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation
  作者：Jacob B. Geri、Michael M. Wade Wolfe、Nathaniel K. Szymczak

  DOI：10.1002/anie.201711316

  日期：2018.1.26

  A fluoroform‐derived borazine CF3− transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C−H and C−X

  甲三氟甲烷衍生的环硼氮烷CF 3 -转移试剂在25用来快速作用的亲核反应在不存在添加剂时，在几分钟内℃。可以高产率地将跨越周期表的七个基团的无机亲电试剂三氟甲基化，包括用于催化三氟甲基化的过渡金属。有机亲电试剂包括（杂）芳烃，可实现CH和CX三氟甲基化反应。机理分析支持CF解离机构3 -转移，和阳离子改性，得到具有增强的稳定性的试剂。