4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile | 1220912-65-1

• 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: 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
• 英文别名: 4-[2-(2-Chlorophenyl)-vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile；4-[(E)-2-(2-chlorophenyl)ethenyl]-2,2-dimethyl-6-oxo-1,3-dihydropyridine-5-carbonitrile
• CAS: 1220912-65-1
• 化学式: C₁₆H₁₅ClN₂O
• 分子量: 286.761
• InChiKey: IJBHMMGUHHMOIK-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile 以 乙醇 为溶剂， 反应 1.0h， 生成 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  Quantum-chemical investigation of the mechanism of trans-cis photoisomerization of 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

  摘要：

  A quantum-chemical investigation has been carried out by the semiempirical AM1 method of the trans-cis photoisomerization mechanism of 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetra- hydropyridine-3-carbonitrile. It was shown that the isomerization process proceeds in the excited singlet state S-1 by rotation of the 2-chlorophenyl substituent around the C(2)-C(3) bond. Electronic absorption spectra of the isomers were calculated by the INDO/S method Transitions caused by exitation of an electron from HOMO to LUMO were characterized by the greatest intensity.

  DOI：

  10.1007/s10593-012-0944-z
• 作为产物：
  描述：

  二丙酮醇 在 ammonium acetate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-[2-(2-chlorophenyl)vinyl]-6,6-dimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis and cytotoxicity of phenyl-vinyl derivatives of 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

  摘要：

  A series of phenylvinyl derivatives of 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitriles has been synthesized and their cytotoxic activity towards HT-1080 (human fibrosarcoma) and MG 22A (mouse hepatoma) tumor cells studied. It was found that the 2-nitro-, 2- and 3-chloro, 2-fluoro, and 2-bromophenyl derivatives showed high cytotoxic activity towards both cell lines. The toxicity towards NIH 3T3 normal mouse embryonic fibroblasts depends on the nature and position of the substituent in the phenyl ring. The greatest selectivity of cytotoxic effect was seen in the 2-bromophenyl derivative.

  DOI：

  10.1007/s10593-010-0411-7