(E)-2-(N-methylanilino)penta-2,4-dienenitrile | 132431-20-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-2-(N-methylanilino)penta-2,4-dienenitrile
• 英文别名: (E)-2-(methyl(phenyl)amino)penta-2,4-dienenitrile；(2E)-2-(N-methylanilino)penta-2,4-dienenitrile
• CAS: 132431-20-0
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: FMTDJEZIAYUXIL-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 (E)-2-(N-methylanilino)penta-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

• Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement
  作者：Meng-Guang Zhou、Rui-Han Dai、Shi-Kai Tian

  DOI：10.1039/c8cc02176g

  日期：——

  In the presence of 2-(trimethylsilyl)aryl triflates as aryne precursors under mild conditions, a range of tertiary propargylic amines bearing electron-withdrawing groups were converted to quaternary propargylic ammonium ylides followed by a [2,3]-sigmatropic rearrangement to afford structurally diverse amino-substituted allenes or conjugated dienes, depending on their structure, in moderate to good

  在2-（三甲基甲硅烷基）芳基三氟甲磺酸酯作为芳烃前体的条件下，在温和条件下，将一系列带有吸电子基团的叔炔丙基胺转化为季炔丙基戊基铵，然后进行[2,3]-σ重排，从而结构上得到取决于它们的结构，以中等到良好的收率得到各种氨基取代的烯或共轭二烯。
• 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：——
• 2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions
  作者：Chih-Cheng Chen、Same-Ting Chen、Tsung-Hsun Chuang、Jim-Min Fang

  DOI：10.1039/p19940002217

  日期：——

  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.