N-Methyl-2-cyano-3-phenylpropenamide | 25695-85-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-Methyl-2-cyano-3-phenylpropenamide
• 英文别名: N-methyl-3-phenyl-2-cyanoacrylamide；Benzyliden-cyan-methylacetamid；N-Methyl-α-cyan-zimtsaeureamid；2-Cyan-3-phenyl-N-methyl-acrylsaeureamid；(E)-2-cyano-N-methyl-3-phenylprop-2-enamide
• CAS: 25695-85-6
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: NSYFWCIFXIOERH-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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-溴-2-甲基苯丙酮 、 N-Methyl-2-cyano-3-phenylpropenamide 在 锌 作用下， 以 六甲基磷酰三胺 、 乙醚 为溶剂， 以59%的产率得到6-hydroxy-1,5,5-trimethyl-2-oxo-4,6-diphenylpiperidine-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 4,6-diaryl-1-benzyl-6-hydroxy-5,5-dimethyl-2-oxopiperidine-3-carbonitriles and their analogs via a modified Reformatsky reaction

  摘要：

  Organozinc compounds obtained from 1-aryl-2-bromo-2-methylpropanone and zinc react with N-benzyl-3-aryl-2-cyanoacrylamides or N-[6-(2-cyano-1-oxo-3-phenylprop-2-enylamino)hexyl]-2-cyano-3-phenylacrylamide to give 4,6-diaryl-1-benzyl-6-hydroxy-5,5-dimethyl-2-oxopiperidine-3-carbonitriles or 1,6-bis(6-aryl-3-cyano-6-hydroxy-5,5-dimethyl-2-oxo-4-phenylpiperidyl)hexanes as a single isomer with translocated piperidine hydrogen atoms.

  DOI：

  10.1134/s1070363206110247

文献信息

• A Simple Synthesis of 4-Amino-6-aryl-2-thioxotetra-and -hexahydropyrimidines
  作者：Antonio Lorente、José L. Garacia Navio、José C. Lopez Perez、José L. Soto

  DOI：10.1055/s-1985-31121

  日期：——
• LORENTE, A.;GARCIA, NAVIO, J. L.;LOPEZ, PEREZ, J. C.;SOTO, J. L., SYNTHESIS, BRD, 1985, N 1, 89-92
  作者：LORENTE, A.、GARCIA, NAVIO, J. L.、LOPEZ, PEREZ, J. C.、SOTO, J. L.

  DOI：——

  日期：——
• LORENTE A.; SOTO J. L., AFINIDAD, 1978, 35, NO 354, 138-140
  作者：LORENTE A.、 SOTO J. L.

  DOI：——

  日期：——
• Synthesis of 4,6-diaryl-1-benzyl-6-hydroxy-5,5-dimethyl-2-oxopiperidine-3-carbonitriles and their analogs via a modified Reformatsky reaction
  作者：V. V. Shchepin、Yu. G. Stepanyan、P. S. Silaichev、N. U. Russkikh、S. N. Shnurov、A. R. Rakitin

  DOI：10.1134/s1070363206110247

  日期：2006.11

  Organozinc compounds obtained from 1-aryl-2-bromo-2-methylpropanone and zinc react with N-benzyl-3-aryl-2-cyanoacrylamides or N-[6-(2-cyano-1-oxo-3-phenylprop-2-enylamino)hexyl]-2-cyano-3-phenylacrylamide to give 4,6-diaryl-1-benzyl-6-hydroxy-5,5-dimethyl-2-oxopiperidine-3-carbonitriles or 1,6-bis(6-aryl-3-cyano-6-hydroxy-5,5-dimethyl-2-oxo-4-phenylpiperidyl)hexanes as a single isomer with translocated piperidine hydrogen atoms.