N-(1-cyano-1-phenylethyl)-4-methylbenzenesulfonamide | 5537-48-4

• 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: N-(1-cyano-1-phenylethyl)-4-methylbenzenesulfonamide
• CAS: 5537-48-4
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: RQJXSEGDVRFHFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  470.6±55.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[cyano(phenyl)methyl]-4-methylbenzenesulfonamide 以85%的产率得到
  参考文献：
  名称：

  77-1780 GLA; SS R. S.H, ZH0148 77TETRANEDRON LETT. , 1976, NO 21, 17

  摘要：

  DOI：

文献信息

• Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C–H Cyanation
  作者：Shasha Shi、Xianyu Yang、Man Tang、Jiefeng Hu、Teck-Peng Loh

  DOI：10.1021/acs.orglett.1c01232

  日期：2021.5.21

  Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C–H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification

  在这里，我们公开了一种无过渡金属的反应体系，该体系可使磺酰胺通过C–H键断裂进行α-氰化，以制备α-氨基腈，包括难以接近的全烷基α-叔骨架。超过50个底物实例证明了广泛的官能团耐受性。另外，其合成实用性通过克可缩放性和天然化合物的后期修饰得到突出。机理实验表明，该过程涉及通过碱促进的HF的消除而原位形成亚胺中间体。
• Asymmetric Strecker Reaction of Ketoimines Catalyzed by a Novel Chiral BifunctionalN,N′-Dioxide
  作者：Xiao Huang、Jinglun Huang、Yuehong Wen、Xiaoming Feng

  DOI：10.1002/adsc.200600238

  日期：2006.12

  A novel bifunctional N,N′-dioxide derived from L-prolinamide was employed to catalyze the enantioselective Strecker reaction of a range of N-tosyl ketoimines, and an effective additive was used to improve the reactivity (up to 99 % yield) as well as the enantioselectivity (up to 91 % ee). In addition, a rational transition state was proposed to elucidate the origin of chiral induction in which an S-adduct

  衍生自L-脯氨酰胺的新型双官能N，N'-二氧化物被用于催化一系列N-甲苯磺酰基酮亚胺的对映选择性Strecker反应，并且还使用有效的添加剂来提高反应性（产率高达99％）。作为对映选择性（高达91％ee）。另外，提出了一种合理的过渡态以阐明其中产生S-加合物的手性诱导的起源。
• Construction of Tetrasubstituted Carbon by an Organocatalyst: Cyanation Reaction of Ketones and Ketimines Catalyzed by a Nucleophilic N-Heterocyclic Carbene
  作者：Kazuhiro Kondo、Toyohiko Aoyama、Yoshimasa Fukuda

  DOI：10.1055/s-2006-942483

  日期：2006.8

  cyanation reaction of ketones and ketimines having lower reactivity than aldehydes and aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and potassium tert-butoxide, as a nucleophilic organocatalyst, is described. These cyanations of ketones and ketimines afford the corresponding products in good yields under mild reaction conditions

  一种在由1,3-双(2,4,6-三甲基苯基)咪唑氯化物和叔丁醇钾制备的N-杂环卡宾存在下使反应性低于醛和醛亚胺的酮和酮亚胺与TMSCN进行氰化反应的方法，描述了作为亲核有机催化剂。酮和酮亚胺的这些氰化反应在温和的反应条件下以良好的收率提供相应的产物。
• Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene
  作者：Taichi Kano、Kouji Sasaki、Teppei Konishi、Haruka Mii、Keiji Maruoka

  DOI：10.1016/j.tetlet.2006.04.141

  日期：2006.7

  The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields.

  N-杂环卡宾的合成用途通过醛，酮和亚胺的三烷基甲硅烷基氰化来证明。在催化量3a的存在下，与Me 3 SiCN的反应平稳进行，以良好的产率获得了相应的氰醇三甲基甲硅烷基醚或氨基腈衍生物。
• Lewis Base-catalyzed Strecker-type Reaction between Trimethylsilyl Cyanide and<i>N</i>-Tosylimines in Water-containing DMF
  作者：Eiki Takahashi、Hidehiko Fujisawa、Toshiharu Yanai、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.318

  日期：2005.3

  Lewis base-catalyzed Strecker-type reaction between trimethylsilyl cyanide and N-tosylimines proceeded smoothly in dry DMF or water-containing DMF and the corresponding α-amino compounds were obtained in good to high yields.

  路易斯碱催化的斯特雷克反应在干燥的DMF或含水的DMF中顺利进行，三甲基硅基氰和N-托希氨基之间反应得到了相应的α-氨基化合物，其收率良好到很高。