1-benzyl-3,5-pyrazoledicarbaldehyde | 244217-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyl-3,5-pyrazoledicarbaldehyde
• 英文别名: N-benzyl-3,5-diformylpyrazole；1-Benzylpyrazole-3,5-dicarbaldehyde
• CAS: 244217-84-3
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: LDDNHZOEKAEDFG-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C(Solv: hexane (110-54-3))
• 沸点：
  426.8±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3,5-pyrazoledicarbaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1^11,14]-octacosa-1(27),11,14(28),24-tetraene
  参考文献：
  名称：

  In Vitro and in Vivo Trypanosomicidal Activity of Pyrazole-Containing Macrocyclic and Macrobicyclic Polyamines: Their Action on Acute and Chronic Phases of Chagas Disease

  摘要：

  The in vitro and in vivo anti-Trypanosoma cruzi activity of the pyrazole-containing macrobicyclic polyamine 1 and N-methyl- and N-benzyl-substituted monocyclic polyamines 2 and 3 was studied. Activity against both the acute and chronic phases of Chagas disease was considered. The compounds were more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, but 1 and 2 were especially effective, where cryptand 1 was the most active, particularly in the chronic phase. The activity results found for these compounds were complemented and discussed by considering their inhibitory effect on the iron superoxide dismutase enzyme of the parasite, the nature of the metabolites excreted after treatment, and the ultrastructural alterations produced. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug and that 1 and 2 exhibited lower levels of damage than 3.

  DOI：

  10.1021/jm2017144
• 作为产物：
  描述：

  1-benzyl-3,5-bis(hydroxymethyl)pyrazole 在 manganese(IV) oxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 以90%的产率得到1-benzyl-3,5-pyrazoledicarbaldehyde
  参考文献：
  名称：

  Synthesis and Protonation Behavior of 26-Membered Oxaaza and Polyaza Macrocycles Containing Two Heteroaromatic Units of 3,5-Disubstituted Pyrazole or 1-Benzylpyrazole. A Potentiometric and ¹H and ¹³C NMR Study

  摘要：

  The synthesis and acid-base behavior of two series of 26-membered dioxatetraamine and hexaamine heterocyclophanes containing two nuclei of either pyrazole (4a and 6a) or 1-benzylpyrazole (4b and 6b), respectively, are reported. Dipodal (2 + 2) condensations of 3,5-pyrazoledicarbaldehyde 2a or its 1-benzyl derivative 2b with 1,5-diamino-3-oxapentane afford in both cases the stable Schiff bases 3a,b in 90% yield, which after reduction with NaBH4 gave 4a;b in 75% and 84% yield, respectively. Condensation of 2a with diethylenetriamine leads to a complex mixture containing imidazolidine isomers, which was reduced in situ to afford 6a in 30% yield. Condensation of 2b with the same amine gave the stable diimidazolidine derivative 5b, which after crystallization was isolated as a pure compound in 80% yield and fully identified from analytical and H-1 and C-13 NMR data as a constitutional isomer with both imidazolidine rings located at the side of the pyrazole closer to the benzylic substituents. Reduction of 5b with NaBH4 afforded the polyamine 6b in 86% yield. Protonation constants of 4a,b and 6a,b have been determined by potentiometric methods in the pH 2-11 range, and their protonation sequences were established by a H-1 and C-13 NMR study in D2O at variable pH. For each compound, the number of protonation constants equals the number of nitrogens in the side chains. In the pH range studied, the pyrazole rings are not involved in protonation or deprotonation processes.

  DOI：

  10.1021/jo981699i

文献信息

• Supramolecular dimeric structures of pyrazole-containing <i>meso</i>-oxo carbaphlorin analogues
  作者：Masatoshi Ishida、Hiroyuki Fujimoto、Tatsuki Morimoto、Shigeki Mori、Motoki Toganoh、Soji Shimizu、Hiroyuki Furuta

  DOI：10.1080/10610278.2016.1158408

  日期：2017.1.2

  Abstract Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin

  摘要 描述了嵌入无 N 吡唑部分的新型内消旋氧代卡夫林类似物的合成和性质。N-苄基前体通过 N-苄基吡唑二醛和 β-烷基取代的三吡喃二羧酸的 [3 + 1]-MacDonald 缩合反应和随后的氯化铁氧化制备。在苄基脱保护后，所得的无 N 氧叶绿素类似物通过吡唑 NH 和内羰基之间的相互氢键相互作用形成独特的超分子二聚体。组装行为的特征在于各种光谱学、X 射线晶体学分析和蒸汽压渗透法。在相似的反应条件下，中间苯基取代的三吡喃衍生物缩合得到前所未有的四吡咯大环与 2,3-二氯-5 稠合，6-二氰基-1,4-苯醌单元在其α-吡咯位置。大环的 X 射线晶体学分析揭示了扭曲的核心结构，并阐明了非芳香性。
• Synthesis and binding studies of new bis-calix[4]arenes containing aromatic and heteroaromatic units
  作者：Manoj Kumar、Vandana Sharma nee Bhalla、J Nagendra Babu

  DOI：10.1016/s0040-4020(03)00409-5

  日期：2003.4

  A series of new bis-calix[4]arenes containing different aromatic and heteroaromatic moieties have been synthesized. The complexing behavior of these bis-calix[4]arenes have been studied towards different metal ions and it has been found that these bis-calix[4]arenes bind silver ions selectively over other metal ions. The complexation has been studied by liquid-liquid extraction and by NMR and IR spectroscopy. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and Protonation Behavior of 26-Membered Oxaaza and Polyaza Macrocycles Containing Two Heteroaromatic Units of 3,5-Disubstituted Pyrazole or 1-Benzylpyrazole. A Potentiometric and ¹H and ¹³C NMR Study
  作者：Vicente J. Arán、Manoj Kumar、José Molina、Laurent Lamarque、Pilar Navarro、Enrique García-España、José A. Ramírez、Santiago V. Luis、Beatriz Escuder

  DOI：10.1021/jo981699i

  日期：1999.8.1

  The synthesis and acid-base behavior of two series of 26-membered dioxatetraamine and hexaamine heterocyclophanes containing two nuclei of either pyrazole (4a and 6a) or 1-benzylpyrazole (4b and 6b), respectively, are reported. Dipodal (2 + 2) condensations of 3,5-pyrazoledicarbaldehyde 2a or its 1-benzyl derivative 2b with 1,5-diamino-3-oxapentane afford in both cases the stable Schiff bases 3a,b in 90% yield, which after reduction with NaBH4 gave 4a;b in 75% and 84% yield, respectively. Condensation of 2a with diethylenetriamine leads to a complex mixture containing imidazolidine isomers, which was reduced in situ to afford 6a in 30% yield. Condensation of 2b with the same amine gave the stable diimidazolidine derivative 5b, which after crystallization was isolated as a pure compound in 80% yield and fully identified from analytical and H-1 and C-13 NMR data as a constitutional isomer with both imidazolidine rings located at the side of the pyrazole closer to the benzylic substituents. Reduction of 5b with NaBH4 afforded the polyamine 6b in 86% yield. Protonation constants of 4a,b and 6a,b have been determined by potentiometric methods in the pH 2-11 range, and their protonation sequences were established by a H-1 and C-13 NMR study in D2O at variable pH. For each compound, the number of protonation constants equals the number of nitrogens in the side chains. In the pH range studied, the pyrazole rings are not involved in protonation or deprotonation processes.
• In Vitro and in Vivo Trypanosomicidal Activity of Pyrazole-Containing Macrocyclic and Macrobicyclic Polyamines: Their Action on Acute and Chronic Phases of Chagas Disease
  作者：Manuel Sánchez-Moreno、Clotilde Marín、Pilar Navarro、Laurent Lamarque、Enrique García-España、Carlos Miranda、Oscar Huertas、Francisco Olmo、Fernando Gómez-Contreras、Javier Pitarch、Francisco Arrebola

  DOI：10.1021/jm2017144

  日期：2012.5.10

  The in vitro and in vivo anti-Trypanosoma cruzi activity of the pyrazole-containing macrobicyclic polyamine 1 and N-methyl- and N-benzyl-substituted monocyclic polyamines 2 and 3 was studied. Activity against both the acute and chronic phases of Chagas disease was considered. The compounds were more active against the parasite and less toxic against Vero cells than the reference drug benznidazole, but 1 and 2 were especially effective, where cryptand 1 was the most active, particularly in the chronic phase. The activity results found for these compounds were complemented and discussed by considering their inhibitory effect on the iron superoxide dismutase enzyme of the parasite, the nature of the metabolites excreted after treatment, and the ultrastructural alterations produced. A complementary histopathological analysis confirmed that the compounds tested were significantly less toxic to mammals than the reference drug and that 1 and 2 exhibited lower levels of damage than 3.