6-chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde | 1227809-87-1

• 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: 6-chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde
• 英文别名: 6-Chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde
• CAS: 1227809-87-1
• 化学式: C₂₀H₁₃Cl₂N₃O
• 分子量: 382.249
• InChiKey: WURWHXZYUJTSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.25h， 以70%的产率得到4-(4-chlorophenyl)-3-methyl-1-phenyl-1H,7H-dipyrazolo[3,4-b:4',3'-e]pyridine
  参考文献：
  名称：

  Preparation of 6-chloropyrazolo[3,4-b]pyridine-5-carbaldehydes by Vilsmeier–Haack reaction and its use in the synthesis of heterocyclic chalcones and dipyrazolopyridines

  摘要：

  Novel 6-chloropyrazolo[3,4-b]pyridine-5-carbaldehydes 5 have been synthesized from the 4,5-dihydropyrazolo[3,4-b]pyridine-6-ones 4 via Vilsmeier-Haack reaction. Further treatment of carbaldehydes 5 with acetophenones 6 and hydrazine hydrate afforded chalcone analogues 7 and dipyrazolo[3,4-6:4',3'e]pyridines 8, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.117
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 4-(4-chlorophenyl)-3-methyl-1-phenyl-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one 在 三氯氧磷 作用下， 反应 5.5h， 生成 6-chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde
  参考文献：
  名称：

  Hydrogen-bonded assembly in six closely related pyrazolo[3,4-b]pyridine derivatives; a simple chain, three types of chains of rings and a complex sheet structure

  摘要：

  六种密切相关的吡唑并[3,4-b]吡啶衍生物，即 6-氯-3-甲基-1,4-二苯基吡唑并[3,4-b]吡啶-5-甲醛，C20H14ClN3O，(I)，6-氯-3-甲基-4-(4-甲基苯基)-1-苯基吡唑并[3、(II), 6-氯-4-(4-氯苯基)-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛, C20H13Cl2N3O, (III), 4-(4-溴苯基)-6-氯-3-甲基-1-苯基吡唑并[3、4-(4-溴苯基)-6-氯-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛，C20H13BrClN3O，(IV)，6-氯-4-(4-甲氧基苯基)-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛，C21H16ClN3O2，(V)，和 6-氯-3-甲基-4-(4-硝基苯基)-1-苯基吡唑并[3、4-b]吡啶-5-甲醛，C20H13ClN4O3，(VI)，它们的区别仅在于其中一个芳基环上的一个小取代基，在四个不同的空间群中结晶，跨越三个晶系。(I)的分子通过 C-H...N和C-H...π（arene）氢键组合连接成环链；(II)、(IV)和(V)的分子都在空间群P/overline{1}中结晶，每个分子都通过两个独立的C-H...O氢键连接成边缘链。O氢键连接，形成沿不同方向贯穿三个单元格的边缘融合环链；(III)的分子通过两个C-H...O氢键和一个C-H...π（arene）氢键组合连接成复杂的薄片；最后，(VI)的分子通过一个C-H...O氢键连接成简单的链。

  DOI：

  10.1107/s0108270111050207

文献信息

• Preparation of 6-chloropyrazolo[3,4-b]pyridine-5-carbaldehydes by Vilsmeier–Haack reaction and its use in the synthesis of heterocyclic chalcones and dipyrazolopyridines
  作者：Jairo Quiroga、Yurina Diaz、Braulio Insuasty、Rodrigo Abonıa、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.tetlet.2010.03.117

  日期：2010.5

  Novel 6-chloropyrazolo[3,4-b]pyridine-5-carbaldehydes 5 have been synthesized from the 4,5-dihydropyrazolo[3,4-b]pyridine-6-ones 4 via Vilsmeier-Haack reaction. Further treatment of carbaldehydes 5 with acetophenones 6 and hydrazine hydrate afforded chalcone analogues 7 and dipyrazolo[3,4-6:4',3'e]pyridines 8, respectively. (C) 2010 Elsevier Ltd. All rights reserved.
• Hydrogen-bonded assembly in six closely related pyrazolo[3,4-<i>b</i>]pyridine derivatives; a simple chain, three types of chains of rings and a complex sheet structure
  作者：Jairo Quiroga、Yurina Díaz、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270111050207

  日期：2012.1.15

  Six closely related pyrazolo[3,4-b]pyridine derivatives, namely 6-chloro-3-methyl-1,4-diphenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₀H₁₄ClN₃O, (I), 6-chloro-3-methyl-4-(4-methylphenyl)-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₁H₁₆ClN₃O, (II), 6-chloro-4-(4-chlorophenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₀H₁₃Cl₂N₃O, (III), 4-(4-bromophenyl)-6-chloro-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₀H₁₃BrClN₃O, (IV), 6-chloro-4-(4-methoxyphenyl)-3-methyl-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₁H₁₆ClN₃O₂, (V), and 6-chloro-3-methyl-4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-b]pyridine-5-carbaldehyde, C₂₀H₁₃ClN₄O₃, (VI), which differ only in the identity of a single small substituent on one of the aryl rings, crystallize in four different space groups spanning three crystal systems. The molecules of (I) are linked into a chain of rings by a combination of C—H...N and C—H...π(arene) hydrogen bonds; those of (II), (IV) and (V), which all crystallize in the space groupP\overline1}, are each linked by two independent C—H...O hydrogen bonds to form chains of edge-fused rings running in different directions through the three unit cells; the molecules of (III) are linked into complex sheets by a combination of two C—H...O hydrogen bonds and one C—H...π(arene) hydrogen bond; finally, the molecules of (VI) are linked by a single C—H...O hydrogen bond to form a simple chain.

  六种密切相关的吡唑并[3,4-b]吡啶衍生物，即 6-氯-3-甲基-1,4-二苯基吡唑并[3,4-b]吡啶-5-甲醛，C20H14ClN3O，(I)，6-氯-3-甲基-4-(4-甲基苯基)-1-苯基吡唑并[3、(II), 6-氯-4-(4-氯苯基)-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛, C20H13Cl2N3O, (III), 4-(4-溴苯基)-6-氯-3-甲基-1-苯基吡唑并[3、4-(4-溴苯基)-6-氯-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛，C20H13BrClN3O，(IV)，6-氯-4-(4-甲氧基苯基)-3-甲基-1-苯基吡唑并[3,4-b]吡啶-5-甲醛，C21H16ClN3O2，(V)，和 6-氯-3-甲基-4-(4-硝基苯基)-1-苯基吡唑并[3、4-b]吡啶-5-甲醛，C20H13ClN4O3，(VI)，它们的区别仅在于其中一个芳基环上的一个小取代基，在四个不同的空间群中结晶，跨越三个晶系。(I)的分子通过 C-H...N和C-H...π（arene）氢键组合连接成环链；(II)、(IV)和(V)的分子都在空间群P/overline1}中结晶，每个分子都通过两个独立的C-H...O氢键连接成边缘链。O氢键连接，形成沿不同方向贯穿三个单元格的边缘融合环链；(III)的分子通过两个C-H...O氢键和一个C-H...π（arene）氢键组合连接成复杂的薄片；最后，(VI)的分子通过一个C-H...O氢键连接成简单的链。