2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide | 23530-19-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide
• 英文别名: 3,3-dichloro-2-(2-chloro-acetylamino)-acrylonitrile；α-<(Chloracetyl)-amino>-β,β-dichloracrylnitril；β,β-Dichlor-α-chloracetamido-acrylnitril；Acetamide, 2-chloro-N-(2,2-dichloro-1-cyanoethenyl)-；2-chloro-N-(2,2-dichloro-1-cyanoethenyl)acetamide
• CAS: 23530-19-0
• 化学式: C₅H₃Cl₃N₂O
• mdl: MFCD00466552
• 分子量: 213.451
• InChiKey: XLBHIDXDGGJQJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  330.6±42.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide 以 水 、 乙腈 为溶剂， 反应 12.0h， 生成 {[4-cyano-5-(dimethylamino)-1,3-oxazol-2-yl]methyl}trimethylammonium iodide
  参考文献：
  名称：

  Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles

  摘要：

  Reaction of 2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide with dimethylamine gave 5-(dimethylamino)-2-[(dimethylamino)methyl]-1,3-oxazole-4-carbonitrile, where aliphatic dimethylamino group was regioselectively alkylated with iodomethane. The resulting trimethylammonium salt reacted diastereoselectively with aromatic aldehydes to form new substituted 2-(oxiran-2-yl)-1,3-oxazoles.

  DOI：

  10.1134/s1070363218070307
• 作为产物：
  描述：

  N-(1,2,2,2-四氯乙基)氯乙酰胺 、 氰化钾 以74%的产率得到
  参考文献：
  名称：

  DRACH B. S.; MISKEVICH G. N., ZH. ORGAN. XIMII, 1978, 14, HO 3, 501-507

  摘要：

  DOI：

文献信息

• ——
  作者：S. G. Pil'o

  DOI：10.1023/a:1023333011230

  日期：——

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.
• Drach,B.S.; Mis'kevich,G.N., Journal of Organic Chemistry USSR (English Translation), 1978, vol. 14, p. 463 - 469
  作者：Drach,B.S.、Mis'kevich,G.N.

  DOI：——

  日期：——
• Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles
  作者：O. V. Shablykin、M. A. Volosheniuk、V. S. Brovarets

  DOI：10.1134/s1070363218070307

  日期：2018.7

  Reaction of 2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide with dimethylamine gave 5-(dimethylamino)-2-[(dimethylamino)methyl]-1,3-oxazole-4-carbonitrile, where aliphatic dimethylamino group was regioselectively alkylated with iodomethane. The resulting trimethylammonium salt reacted diastereoselectively with aromatic aldehydes to form new substituted 2-(oxiran-2-yl)-1,3-oxazoles.
• DRACH B. S.; MISKEVICH G. N., ZH. ORGAN. XIMII, 1978, 14, HO 3, 501-507
  作者：DRACH B. S.、 MISKEVICH G. N.

  DOI：——

  日期：——