2-amino-5-cyano-6-ethoxy-3-formyl-4-phenylpyridine | 97125-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-5-cyano-6-ethoxy-3-formyl-4-phenylpyridine
• 英文别名: 2-ethoxy-6-amino-3-cyano-5-formyl-4-phenylpyridine；6-amino-3-cyano-2-ethoxy-5-formyl-4-phenylpyridine；2-amino-5-cyano-6-ethoxy-4-phenylpyridine-3-carbaldehyde；6-Amino-2-ethoxy-5-formyl-4-phenylnicotinonitrile；6-amino-2-ethoxy-5-formyl-4-phenylpyridine-3-carbonitrile
• CAS: 97125-17-2
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: IEMPEJJXRNFGEN-UHFFFAOYSA-N

物化性质

• 沸点：
  475.9±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5-cyano-6-ethoxy-3-formyl-4-phenylpyridine 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3-cyano-2-ethoxy-6-ethoxycarbonyl-7-<2-(N,N-dimethylamino)ethenyl>-4-phenyl-1,8-naphthyridine
  参考文献：
  名称：

  Vilar, Juan; Quintela, Jose M.; Peinador, Carlos, Heterocycles, 1993, vol. 36, # 12, p. 2697 - 2706

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-6-乙氧基-4-苯基吡啶-3,5-二腈 在 lithium aluminium tetrahydride 作用下， 生成 2-amino-5-cyano-6-ethoxy-3-formyl-4-phenylpyridine
  参考文献：
  名称：

  Synthesis of new bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites

  摘要：

  A series of new 2-[1,8]naphthyridinyl and bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites were prepared using 2-amino-5-cyano-6-ethoxy-4-phenyl-3-carbaldehyde pyridine as excellent Friedlander synthon. Condensation with a series of acetyl(heteroaryl)-aromatics provides the corresponding 2-aryl(heteroaryl)-1,8-naphthyridines. Reaction with 1,3-diacetylbenzene, 2,6-diacetylpyridine or 4-tertbutyl-2.6-diacetylpyridine provides the expected Friedlander product. Similar 2:1 condensation with 1,4-diacetylbenzene, 4,4'-diacetylbiphenyl, 1,4- and 1,6-diacetylpyrene, 2,6-diacetylpyrazine or 2,3-butanedione leads to a family of six new bis-1,8-nap ligands. The reaction with cyclic 1.2- or 1.3-diketones affords 3,3'-annelated derivatives of all-syn or all-trans planar 2,2'-nap, respectively. Examination of the electronic absorption and emission spectra of the bridging ligands was realized. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.017

文献信息

• Piperazine N-substituted naphthyridines, pyridothienopyrimidines and pyridothienotriazines: new antiprotozoals active against Philasterides dicentrarchi
  作者：José M Quintela、Carlos Peinador、Liliana González、Raúl Iglesias、Anabel Paramá、Francisca Álvarez、Manuel L Sanmartı́n、Ricardo Riguera

  DOI：10.1016/s0223-5234(03)00032-1

  日期：2003.3

  New antiprotozoals active against Philasterides dicentrarchi, the causative agent of scuticociliatosis in farmed turbot and Black Sea bass-bream, have been synthesised and tested. The most active compounds posses a piperazine ring, generally N-bonded to the heterocycle, and are the 1,8-naphthyridines, 2f and 5o, the pyridothienopyrimidine (7), and the pyridothienotriazines, 8, 9, 12d, 12f, 12h, 12m

  合成和测试了新的抗原生动物动物，它们对养殖费氏鱼和黑海鲈鱼中的刀oci病的致病因子Philasterides dicentrarchi具有活性。活性最高的化合物通常具有N键合至杂环的哌嗪环，分别为1,8-萘啶2f和5o，吡啶并吡啶并嘧啶（7）和吡啶并噻吩并三嗪8、9、12d，12f，12h， 12m和12k。吡啶并三嗪（12k）具有与众所周知的抗寄生虫药niclosamide和oxyclozanide相同的活性（致死剂量，LD = 0.8 / 1.5 mg L（-1））。
• Synthesis of New Heterotricyclic Compounds Containing the [1,8]Naphthyridine Group by Thermal Isomerization of 2-Dialkylamino-3-vinylpyridines
  作者：Vicente Ojea、Carlos Peinador、José M. Quintela

  DOI：10.1055/s-1992-26229

  日期：——

  2-N,N-Dialkylamino-3-(2,2-dicyanovinyl)pyridines react thermally in polar solvents via [1,5] hydrogen transfer followed by carbon-carbon bond formation to yield heterotricyclic compounds containing the [1,8]naphthyridine group. The reaction time is markedly dependent on the solvent used and the stereoelectronic effects of the amino moiety. The presence of thiazolidinyl group results in the thermal isomerization taking place regiospecifically.

  2-N,N-二烷基氨基-3-(2,2-二氰乙烯基)吡啶在极性溶剂中通过[1,5]氢转移反应，随后形成碳-碳键，生成含有[1,8]萘啶结构的异杂环化合物。反应时间显著依赖于所用溶剂和氨基部分的立体电子效应。噻唑烷基团的存在导致热异构化以区域选择性发生。
• Novel naphthyridine-based compounds in small molecular non-doped OLEDs: synthesis, properties and their versatile applications for organic light-emitting diodes
  作者：Antonio Fernández-Mato、José M. Quintela、Carlos Peinador

  DOI：10.1039/c2nj40279c

  日期：——

  A series of six new n-type conjugated 1,8-naphthyridine oligomers were examined in organic light emitting diodes (OLEDs). The compounds show a high fluorescence in both solution (10−8 M) and the solid state. The naphthyridines have high glass-transition (Tg = 65–105 °C) and decomposition (Td = 380–400 °C) temperatures, reversible electrochemical reduction, and high electron affinities (2.79–3.00 eV). Systematic variation of the spacer linkage can modulate and fine-tune their properties. They emit high blue, green and yellow photoluminescence with 0.70–1.0 quantum yields. Good-performance, single-layer emitter OLEDs with yellow to white-pink emission have also been demonstrated using these materials. White-pink emitter give a performance with a high brightness (400 cd m−2 at 4 V), and 0.6 cd A−1. Yellow emitters give the best performance with maximum brightness of 250 cd m−2 with a maximum current efficiency of 1.2 cd A−1. These results demonstrate the potential of this new class of n-type conjugated oligomers as emitters and electron-transport materials for developing high-performance yellow to white-pink OLEDs.

  在有机发光二极管（OLED）中研究了一系列六种新型 n 型共轭 1,8-萘啶低聚物。这些化合物在溶液（10-8 M）和固态下都显示出较高的荧光。萘啶类化合物具有较高的玻璃转化温度（Tg = 65-105 ℃）和分解温度（Td = 380-400 ℃）、可逆的电化学还原性和较高的电子亲和力（2.79-3.00 eV）。间隔连接的系统变化可以调节和微调它们的特性。它们能发出蓝色、绿色和黄色的高光致发光，量子产率为 0.70-1.0。利用这些材料还展示了性能良好的单层发射器有机发光二极管，可发出黄色至白粉色的光。白粉色发光体具有高亮度（4 V 时为 400 cd m-2）和 0.6 cd A-1 的性能。黄色发光体的性能最好，最大亮度为 250 cd m-2，最大电流效率为 1.2 cd A-1。这些结果证明了这一新型 n 型共轭低聚物作为发光体和电子传输材料在开发高性能黄色至白色粉红色有机发光二极管方面的潜力。
• A Friedländer Approach to Polycondensed 1,8-Naphthyridine Derivatives
  作者：José Ma. Quintela、Rosa Ma Arcas、Carmen Veiga、Carlos Peinador、Juan Vilar、Vicente Ojea

  DOI：10.3987/com-95-7206

  日期：——
• Quintela, Jose M; Vilar, Juan; Peinador, Carlos, Heterocycles, 1995, vol. 41, # 5, p. 1001 - 1012
  作者：Quintela, Jose M、Vilar, Juan、Peinador, Carlos、Veiga, Carmen、Ojea, Vicente

  DOI：——

  日期：——