(S)-N-(4-cyanobenzylidene)-4-methylbenzenesulfinamide | 919492-00-5

• 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: (S)-N-(4-cyanobenzylidene)-4-methylbenzenesulfinamide
• 英文别名: (S)-N-4-cyanobenzylidene-4-methylbenzenesulfinamide；(S)-(+)-N-(p-cyanobenzylidene)-p-toluensulfinamide
• CAS: 919492-00-5
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: NTKYAQWLSDVLLQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.22
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-cyanobenzylidene)-4-methylbenzenesulfinamide 、 (S)-1-methyl-2-(p-tolylsulfinyl)benzene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以88%的产率得到[1S,(S)S]-N-{1-(4-cyanophenyl)-2-[(S)-2-(p-toluenesulfinyl)phenyl]ethyl}-p-toluensulfinamide
  参考文献：
  名称：

  Facile Synthesis of Optically Pure 1,2-Diaryl (and 1-Alkyl-2-aryl) Ethyl and Propylamines

  摘要：

  [GRAPHICS]A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).

  DOI：

  10.1021/ol027464h
• 作为产物：
  描述：

  (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 、 4-氰基苯甲醛 在 lithium hexamethyldisilazane 作用下， 以60%的产率得到(S)-N-(4-cyanobenzylidene)-4-methylbenzenesulfinamide
  参考文献：
  名称：

  Facile Synthesis of Optically Pure 1,2-Diaryl (and 1-Alkyl-2-aryl) Ethyl and Propylamines

  摘要：

  [GRAPHICS]A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).

  DOI：

  10.1021/ol027464h

文献信息

• 1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of <i>N</i>-sulfinyl imines
  作者：Manjunatha M Ramaiah、Priya Babu Shubha、Pavan Kumar Prabhala、Nanjunda Swamy Shivananju

  DOI：10.1177/1747519819884146

  日期：2020.1

  A facile and efficient method was developed for the preparation of a variety of aryl, heteroaryl, and alkyl N-sulfinyl imines using 1,8-diazabicyclo[5.4.0]undec-7-ene. In addition to tert-butanesulfinamide, the condensation is also effective with p-toluenesulfinamide. The reaction was performed at room temperature and produces the corresponding N-sulfinyl imines in excellent yields in the absence of

  开发了一种使用 1,8-二氮杂双环 [5.4.0] undec-7-ene 制备各种芳基、杂芳基和烷基 N-亚磺酰基亚胺的简便有效的方法。除叔丁烷亚磺酰胺外，缩合对甲苯亚磺酰胺也有效。该反应在室温下进行，并在不存在酸、金属和添加剂的情况下以极好的收率产生相应的 N-亚磺酰基亚胺。该方法也可用于以克规模制备 N-亚磺酰基亚胺。使用芳基和杂芳基醇与叔丁烷亚磺酰胺和对甲苯亚磺酰胺在室温下进行一锅合成，得到相应的 N-亚磺酰亚胺，收率良好。
• Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions. Synthesis of Optically Pure <i>trans</i>-Aziridines
  作者：Yolanda Arroyo、Ángela Meana、J. Félix Rodríguez、M. Ascensión Sanz-Tejedor、Inés Alonso、José L. García Ruano

  DOI：10.1021/jo900381b

  日期：2009.6.5

  (R)-N-Sulfinylimine and (S)-N-sulfinylimine react with the ylide derived from (S)-dimethyl-[2-(p-toluenesulfinyl)phenyl]sulfonium salt, affording trans-2,3-disubstituted aziridines. A complete trans selectivity in low facial diastereoselectivity is observed when the configuration at the sulfur atoms of the reagents is the same. Otherwise, when their configurations are different, the reaction evolved

  （R）-N-亚磺酰亚胺和（S）-N-亚磺酰亚胺与衍生自（S）-二甲基-[2-（对甲苯亚磺酰基）苯基] ulf盐的叶立德反应，得到反式-2,3-二取代的氮丙啶。当试剂的硫原子处的构型相同时，可以观察到低的非对映选择性的完全反式选择性。否则，当它们的构型不同时，反应会随着面部总非对映选择性和顺/反式而发展。比率介于1 / 4.2和1/9之间。理论计算表明反应主要是通过平面自由碳负离子的演化而进行的。过渡态的相对稳定性预测反式/顺式比与实验结果非常吻合。
• Stereocontrolled Addition of Scrambling <i>ortho</i>-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines
  作者：Balú Cruz-Delgado、Ricardo I. Rodríguez、Anielka Rosado-Abón、Rubén Sánchez-Obregón、Francisco Yuste、José Alemán

  DOI：10.1021/acs.orglett.0c00625

  日期：2020.3.20

  An unprecedented behavior of ortho-sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: this peculiar chemodivergency is importantly affected by the nature of the employed base, and assisted by the configuration of the electrophile, displaying no alteration in the stereocontrol of both reactions. alpha-Allenylamines are formed exclusively, using R-sulfinyl aldimines as electrophiles, while homopropargylamines result when S-sulfinyl aldimines are employed.
• Synthesis of Optically Pure 1,2-Diaryl- and 1,2-Alkylaryl-1,2-amino Sulfides
  作者：Yolanda Arroyo、Ángela Meana、J. Félix Rodríguez、Mercedes Santos、M. Ascensión Sanz-Tejedor、José. L. García Ruano

  DOI：10.1021/jo050129x

  日期：2005.5.1

  The reactions of the lithium (S)-alpha-(methylthio)-2-(p-toluenesulfinyl)benzyl carbanion with (S)-N-p-tolylsulfinyl aldimines evolve in a completely stereoselective manner providing a one-step synthesis of enantiomerically pure anti-1,2-disubstituted 1,2-amino sulfide derivatives.
• Synthesis of Enantiomerically Pure <i>anti</i>-1,2-Diaryl and <i>syn</i>-1,2-Alkylaryl <i>vic</i>-Selenoamines
  作者：José L. García Ruano、Esther Torrente、Inés Alonso、Mercedes Rodriguez、Ana M. Martín-Castro、Alessandro Degl’Innocenti、Lucrezia Frateschi、Antonella Capperucci

  DOI：10.1021/jo202611v

  日期：2012.2.17

  Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.