N-allyl-2-chloro-4-cyanoacetanilide | 207992-38-9

• 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-allyl-2-chloro-4-cyanoacetanilide
• 英文别名: N-Allyl-n-(4-cyano-2-chlorophenyl)acetamide；N-(2-chloro-4-cyanophenyl)-N-prop-2-enylacetamide
• CAS: 207992-38-9
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: MLWIDMSZKIMZLY-UHFFFAOYSA-N

物化性质

• 沸点：
  391.4±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-2-chloro-4-cyanoacetanilide 在 N,N,N,N-tetraethylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以25 mg的产率得到1-acetyl-5-cyano-3-methylindoline
  参考文献：
  名称：

  Formation of N-Acetyl-2,3-dihydroindoles by the Electrochemical Cleavage of the Carbon-Chlorine Bond in N-Allyl-2-chloroacetanilides.

  摘要：

  The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.

  DOI：

  10.3891/acta.chem.scand.52-0549
• 作为产物：
  描述：

  N-(2-氯-4-甲基苯基)乙酰胺 在 potassium permanganate 、 磷酸单乙基酯 、 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 63.0h， 生成 N-allyl-2-chloro-4-cyanoacetanilide
  参考文献：
  名称：

  Formation of N-Acetyl-2,3-dihydroindoles by the Electrochemical Cleavage of the Carbon-Chlorine Bond in N-Allyl-2-chloroacetanilides.

  摘要：

  The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.

  DOI：

  10.3891/acta.chem.scand.52-0549

文献信息

• Formation of N-Acetyl-2,3-dihydroindoles by the Electrochemical Cleavage of the Carbon-Chlorine Bond in N-Allyl-2-chloroacetanilides.
  作者：Marylène Dias、Mandy Gibson、James Grimshaw、Ian Hill、Jadwiga Trocha-Grimshaw、Ole Hammerich、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0549

  日期：——

  The electrochemically induced radical cyclization of N-alkyl-2-chloroacetanilides to form N-acetyl-2,3-dihydroindoles has been demonstrated where the phenyl ring contains an electron withdrawing substituent such as cyano. Cyclization of N-alkyl-2-chloroacetanilide was successful in the presence of (E)-stilbene as electron transfer agent yielding 1-acetyl-3-methyl-213-dihydroindole. Indirect electrochemical reduction of N-cinnamyl-2-chloroacetanilide leads mainly to cleavage of the cinnamyl group and only a low yield of N-acetyl-3-benzyl-2,3-dihydroindole was obtained.