1,3,5,7-tetramethyl-4-phenyl-1,7-dihydropyrazolo[3,4-b:4′,3′-e]pyridine | 67985-59-5

• 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: 1,3,5,7-tetramethyl-4-phenyl-1,7-dihydropyrazolo[3,4-b:4′,3′-e]pyridine
• 英文别名: 1,3,5,7-tetramethyl-4-phenyl-1,7-dihydro-dipyrazolo[3,4-b;4',3'-e]pyridine；4,6,10,12-Tetramethyl-8-phenyl-2,4,5,11,12-pentazatricyclo[7.3.0.03,7]dodeca-1,3(7),5,8,10-pentaene
• CAS: 67985-59-5
• 化学式: C₁₇H₁₇N₅
• 分子量: 291.355
• InChiKey: YHDCSVBCNONNTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  bis[5-(benzylideneamino)-1,3-dimethyl-4-pyrazolyl]phenylmethane 以 乙醇 为溶剂， 反应 10.0h， 以67%的产率得到1,3,5,7-tetramethyl-4-phenyl-1,7-dihydropyrazolo[3,4-b:4′,3′-e]pyridine
  参考文献：
  名称：

  Unexpected formation of bis-pyrazolyl derivatives by solid support coupled with microwave irradiation

  摘要：

  Starting from 1,3-dimethyl-5-aminopyrazole 1 and p-substituted benzaldehydes 2 (R=H, CH3, NO2), four different compounds have been obtained: the Schiff bases 4, a bis-pyrazolyl Schiff base 6a (R=H), the expected bispyrazolo[3,4-b;4 ' ,3 ' -e]pyridine 7b (R=CH3) and the carbinol derived from the Schiff base 8c (R=NO2). The products have been characterised by MS, NMR (H-1 and C-13) and X-ray crystallography (in the case of 6a). A proposal for the relationships between the different compounds and a possible mechanism is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00604-4

文献信息

• A mild method for the synthesis of bis-pyrazolo[3,4-b:4′,3′-e]pyridine derivatives
  作者：Rui Qiu、Shujia Qiao、Boyu Peng、Jiajia Long、Guodong Yin

  DOI：10.1016/j.tetlet.2018.09.033

  日期：2018.10

  A mild and efficient method for the synthesis of bispyrazolo[3,4-b:4′,3′-e]pyridines from 5-aminopyrazoles and aromatic aldehydes using an inexpensive FeCl3 catalyst is reported. The reaction temperature was reduced from 220–250 °C to 130 °C compared to conventional methods. A large proportion of the products precipitated directly from the mixture at room temperature. Aliphatic and α,β-unsaturated

  报道了使用廉价的FeCl 3催化剂从5-氨基吡唑和芳族醛合成双吡唑并[3,4- b：4'，3'- e ]吡啶的温和而有效的方法。与传统方法相比，反应温度从220–250°C降至130°C。在室温下，很大一部分产物直接从混合物中沉淀出来。脂肪族和α，β-不饱和醛选择性地导致形成相应的1 H-吡唑并[3,4- b ]吡啶衍生物。还提出了可能的多米诺反应机制。经由Sonogashira偶联反应将几个芳基炔基引入这些三环分子。
• Blue electroluminescence of novel pyrazoloquinoline and bispyrazolopyridine derivatives in doped polymer matrices
  作者：Z. He、G. H. W. Milburn、A. Danel、A. Puchala、P. Tomasik、D. Rasala

  DOI：10.1039/a706561b

  日期：——

  Blue electroluminescence has been demonstrated using novel materials 1,3-diphenyl-4-methyl-1H-pyrazolo[3,4-b]quinoline (PAQ4) and 4-phenyl-1,3,5,7-tetramethyl-1,7-dihydrodipyrazolo[3,4-b;4′,3′-e]pyridine (PAP1) for the first time. The peak maxima of their electroluminescent spectra were at 442 nm (ca. 20 nm shift from its photoluminescent maximum) for PAQ4 and 425 nm (within the same spectral range as the photoluminescence) for PAP1.

  使用新型材料 1,3-二苯基-4-甲基-1H-吡唑并[3,4-b]喹啉 (PAQ4) 和 4-苯基-1,3,5,7-四甲基-1,7 演示了蓝色电致发光-二氢二吡唑并[3,4-b;4',3'-e]吡啶（PAP1）首次出现。 PAQ4 的电致发光光谱的峰值最大值为 442 nm（距其光致发光最大值约 20 nm），PAP1 的电致发光光谱的峰值为 425 nm（与光致发光的光谱范围相同）。
• Electrochemically Enabled Cascade Cyclization Reaction of Aromatic Aldehydes and Pyrazol-5-amines: Synthesis of Bis-pyrazolo[3,4-<i>b</i>:4′,3′-<i>e</i>]pyridines
  作者：Peng Qian、Shan Jiang、Hua Fan、Siqi Jiang、Longlong Xu、Jiaojiao Liu

  DOI：10.1021/acs.joc.2c00988

  日期：2022.7.15

  A facile method for the synthesis of bis-pyrazolo[3,4-b:4′,3′-e]pyridines from easily available aromatic aldehydes and pyrazol-5-amines was developed via electrochemistry. The reaction proceeded smoothly under metal and external chemical oxidant-free conditions, giving a variety of bis-pyrazolo[3,4-b:4′,3′-e]pyridines in moderate yields.

  通过电化学开发了一种从易得的芳香醛和 pyrazol-5- amines合成双吡唑并[3,4- b :4',3' -e ] 吡啶的简便方法。该反应在无金属和外部化学氧化剂的条件下顺利进行，以中等收率得到多种双吡唑并[3,4- b :4',3' -e ]吡啶。
• GONZALEZ E.; SARLIN R.; ELQUERO J., TETRAHEDRON, 1978, 34, NO 8, 1175-1178
  作者：GONZALEZ E.、 SARLIN R.、 ELQUERO J.

  DOI：——

  日期：——
• Unexpected formation of bis-pyrazolyl derivatives by solid support coupled with microwave irradiation
  作者：Andressa Esteves-Souza、Aurea Echevarrı́a、Ivo Vencato、Marı́a Luisa Jimeno、José Elguero

  DOI：10.1016/s0040-4020(01)00604-4

  日期：2001.7

  Starting from 1,3-dimethyl-5-aminopyrazole 1 and p-substituted benzaldehydes 2 (R=H, CH3, NO2), four different compounds have been obtained: the Schiff bases 4, a bis-pyrazolyl Schiff base 6a (R=H), the expected bispyrazolo[3,4-b;4 ' ,3 ' -e]pyridine 7b (R=CH3) and the carbinol derived from the Schiff base 8c (R=NO2). The products have been characterised by MS, NMR (H-1 and C-13) and X-ray crystallography (in the case of 6a). A proposal for the relationships between the different compounds and a possible mechanism is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.