N-4-methylphenyl-C-methoxycarbonylnitrilimine | 492459-29-7

• 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-4-methylphenyl-C-methoxycarbonylnitrilimine
• CAS: 492459-29-7
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: PBDLLNPRDVQXAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-dimethyl-2-thiooxy-1,3-thiazolinyl-5-carboxylate 、 N-4-methylphenyl-C-methoxycarbonylnitrilimine 在 三乙胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 以80%的产率得到8,9-dimethyl-1-(4-methylphenyl)-3-methoxycarbonyl-7-ethoxycarbonyl-4,6-dithia-1,2,9-triazaspiro[4.4]nona-2,7-diene
  参考文献：
  名称：

  1，3-偶极环加成中的杂环硫酮及其类似物：VII。4-甲基-1,3-噻唑-2（3H）-硫酮与腈亚胺的反应

  摘要：

  Reactions of 4-methyl-1,3-thiazole-2(3H)-thiones with various C,N-disubstituted nitrile imines occurred by the common [3+2]-cycloaddition scheme leading to the formation in general of stable spiro compounds. In reactions of o-nitrophenylnitrile imines acyclic compounds were the main products.

  DOI：

  10.1134/s1070428007100193
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-4-methylphenyl-C-methoxycarbonylnitrilimine
  参考文献：
  名称：

  New Routes to Fused Isoquinolines

  摘要：

  Treatment of 6.7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides, 10 in the presence of Et3N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13. respectively, in high yield (Schemes 2 and 3.). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline C=N bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl alpha-cyanocinnamates 15 in the presence of piperidine m refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4), Under the same conditions. 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme5). Instead of 15 and 19, mixtures of an aromatic aldehyde. and ethyl cyanoacetate or malononitrile. respectively can be used in a one-pot reaction.

  DOI：

  10.1002/1522-2675(200201)85:1<320::aid-hlca320>3.0.co;2-x

文献信息

• The diastereoisomers methyl 5-(<i>S</i>)-[2-(<i>R</i>)/(<i>S</i>)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate
  作者：Tullio Pilati、Gianluigi Casalone

  DOI：10.1107/s0108270101021552

  日期：2002.3.15

  The title diastereoisomers, methyl 5-(S)-[2-(S)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methyl- phenyl)-4,5-dihydropyrazole-3-carboxylate and methyl 5-(S)[2-(R)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcar- bonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxyl- ate, both C19H23N3O5, have been studied in two crystalline forms. The first form, methyl 5-(S)-[2-(S)-methoxycarbonyl)2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)- 4,5-dihydropyrazole-3-carboxylate-methyl 5-(S)-[2-(R)-methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]-1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate (1/1), 2(S),5(S)-C19H23N3O5.2(R),5(S)-C19H23N3O5, contains both S,S and S,R isomers, while the second, methyl 5-(S)-[2-(S)methoxycarbonyl)-2,3,4,5-tetrahydropyrrol-1-ylcarbonyl]- 1-(4-methylphenyl)-4,5-dihydropyrazole-3-carboxylate, 2(S),5(S)-C19H23N3O5, is the pure S,S isomer. The S,S isomers in the two structures show very similar geometries, the maximum difference being about 15degrees on one torsion angle. The differences between the S,S and S,R isomers, apart from those due to the inversion of one chiral centre, are more remarkable, and are partially due to a possible rotational disorder of the 2-(methoxycarbonyl)tetrahydropyrrole group.