(2E,4E)-2-(N-methylanilino)-5-phenylsulfanylpenta-2,4-dienenitrile | 132431-26-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E,4E)-2-(N-methylanilino)-5-phenylsulfanylpenta-2,4-dienenitrile
• CAS: 132431-26-6
• 化学式: C₁₈H₁₆N₂S
• 分子量: 292.404
• InChiKey: JDMVWPDUHRJAIE-GAXWWZFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 、 2-(N-methylanilino)-2-phenylthioacetonitrile 在 potassium tert-butylate 作用下， 生成 (2E,4E)-2-(N-methylanilino)-5-phenylsulfanylpenta-2,4-dienenitrile 、 (2Z,4E)-2-(N-methylanilino)-5-phenylsulfanylpenta-2,4-dienenitrile
  参考文献：
  名称：

  2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions

  摘要：

  2-(N-Methylanilino) -2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide. Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates. Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by Cul or Lewis acids to give varied alpha-amino nitriles. The 4-oxo-2-amino nitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung. When 1 was treated with tributylstannane, the corresponding amino nitrile alpha-radical was formed and the self-coupling product was isolated.

  DOI：

  10.1039/p19940002217

文献信息

• 2-(N-Methylanilino)-2-phenylthioacetonitrile: a useful reagent for preparation of conjugated α-amino alkenenitriles via tandem alkylation and dehydrosulphenylation
  作者：Jim-Min Fang、Chin-Cheng Chen

  DOI：10.1039/p19900003365

  日期：——

  Alkylation of the anion of 2-(N-methylanilino)-2-phenylthioacetonitrile 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Counterattack by bromide and benzenethiolate ions was observed in the prolonged reactions of 1 with 1,4-dibromobut-2-ene and 3-bromo-1-(trimethylsilyl)prop-1-yne.
• FANG, JIM-MIN;CHEN, CHIH-CHENG, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N2, C. 3365-3367
  作者：FANG, JIM-MIN、CHEN, CHIH-CHENG

  DOI：——

  日期：——