2-[3-cyano-4,6-bis-(4-methoxyphenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile | 1228010-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3-cyano-4,6-bis-(4-methoxyphenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile
• 英文别名: 2-[5-Cyano-2,4-bis(4-methoxyphenyl)-2-methyl-1,3-dihydropyridin-6-ylidene]propanedinitrile
• CAS: 1228010-36-3
• 化学式: C₂₄H₂₀N₄O₂
• 分子量: 396.448
• InChiKey: LSYQZEYJYDFBDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[3-cyano-4,6-bis-(4-methoxyphenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile 、 苯硫酚 以 水 为溶剂， 反应 1.0h， 以461 mg的产率得到5-amino-1,2-dihydro-2,4-bis(4-methoxyphenyl)-2-methyl-7-(phenylthio)-1,6-naphthyridine-8-carbonitrile
  参考文献：
  名称：

  Pseudo-Five-Component Domino Strategy for the Combinatorial Library Synthesis of [1,6] Naphthyridines—An On-Water Approach

  摘要：

  This work features the base-promoted on-water synthesis of [1,6]-naphthyridines from methyl ketones, malononitrile and phenols or thiols. The reaction conditions were carefully tuned to drive the product selectivity from 3H-pyrroles to [1,6]-naphthyridines. The advantages of this method lie in its simplicity, cost effectiveness, and environmental friendliness, representing a new effort toward the on-water synthesis of [1,6]-naphthyridines without starting from a nitrogen-containing heterocycle and highlighting the versatility of the nitrile functional group.

  DOI：

  10.1021/co400162m
• 作为产物：
  描述：

  2-(1-(4-methoxyphenyl)ethylidene)malononitrile 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到2-[3-cyano-4,6-bis-(4-methoxyphenyl)-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]-malononitrile
  参考文献：
  名称：

  一些新型的聚氮杂稠合杂环化合物的合成

  摘要：

  2-（1-芳基-亚乙基）-丙二腈1a，1b，1c，1d在乙醇中由乙醇钠催化进行自二聚反应，得到2- [4,6-二芳基-3-氰基-6-甲基-5,6-二氢吡啶-2（1 H）-亚烷基]-丙二腈衍生物3a，3b，3c，3d。X射线晶体学阐明了二聚体的结构，并描述了其形成的合理机理。化合物3a与芳烃重氮盐4a，4b，4c，4d偶联，得到肼衍生物5a，5b，5c，5d并与水合肼和苯肼6a，6b反应，得到吡唑并[3,4-h] [1,6]萘啶衍生物7a，7b，并与尿素和硫脲8a，8b反应得到嘧啶基[4,5-h] [1,6]萘啶衍生物9a，9b。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.329

文献信息

• Pseudo-Five-Component Domino Strategy for the Combinatorial Library Synthesis of [1,6] Naphthyridines—An On-Water Approach
  作者：Paramita Das、Tandrima Chaudhuri、Chhanda Mukhopadhyay

  DOI：10.1021/co400162m

  日期：2014.11.10

  This work features the base-promoted on-water synthesis of [1,6]-naphthyridines from methyl ketones, malononitrile and phenols or thiols. The reaction conditions were carefully tuned to drive the product selectivity from 3H-pyrroles to [1,6]-naphthyridines. The advantages of this method lie in its simplicity, cost effectiveness, and environmental friendliness, representing a new effort toward the on-water synthesis of [1,6]-naphthyridines without starting from a nitrogen-containing heterocycle and highlighting the versatility of the nitrile functional group.
• Synthesis of some novel polyaza fused heterocyclic compounds
  作者：Fathy M. Abdelrazek、Nadia H. Metwally、Nazmi A. Kassab、Nehal A. Sobhy、Peter Metz、Anna Jaeger

  DOI：10.1002/jhet.329

  日期：——

  formation is depicted. Compound 3a couples with arene diazonium salts 4a, 4b, 4c, 4d to afford the hydrazo derivatives 5a, 5b, 5c, 5d and reacts with hydrazine hydrate and phenylhydrazine 6a, 6b to afford the pyrazolo[3,4‐h][1,6]naphthyridine derivatives7a, 7b and with urea and thiourea 8a, 8b to afford the pyrimido[4,5‐h][1,6]naphthyridine derivatives 9a, 9b, respectively. J. Heterocyclic Chem., (2010).

  2-（1-芳基-亚乙基）-丙二腈1a，1b，1c，1d在乙醇中由乙醇钠催化进行自二聚反应，得到2- [4,6-二芳基-3-氰基-6-甲基-5,6-二氢吡啶-2（1 H）-亚烷基]-丙二腈衍生物3a，3b，3c，3d。X射线晶体学阐明了二聚体的结构，并描述了其形成的合理机理。化合物3a与芳烃重氮盐4a，4b，4c，4d偶联，得到肼衍生物5a，5b，5c，5d并与水合肼和苯肼6a，6b反应，得到吡唑并[3,4-h] [1,6]萘啶衍生物7a，7b，并与尿素和硫脲8a，8b反应得到嘧啶基[4,5-h] [1,6]萘啶衍生物9a，9b。J.杂环化​​学。（2010）。