1-甲基吡唑-3,5-二甲醛 | 353245-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-甲基吡唑-3,5-二甲醛
• 英文名称: 1-methylpyrazole-3,5-dicarbaldehyde
• 英文别名: 1-Methyl-1H-pyrazole-3,5-dicarbaldehyde
• CAS: 353245-45-1
• 化学式: C₆H₆N₂O₂
• 分子量: 138.126
• InChiKey: RZUDDGKTFLHJDG-UHFFFAOYSA-N

物化性质

• 沸点：
  305.0±27.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-甲基吡唑-3,5-二甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 13,26-dimethyl-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：

  吡唑-3,5-二羧酸二甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 丁酮 为溶剂， 生成 1-甲基吡唑-3,5-二甲醛
  参考文献：
  名称：

  卟啉和氧卟啉的吡唑类似物† ‡

  摘要：

  一系列 卟啉已经合成了具有吡唑环取代了通常的吡咯亚基之一的类似物。这是通过在TFA存在下使1-苯基，1-甲基和1-乙基吡唑-1,3-二甲醛与三吡喃反应，然后进行氧化步骤来实现的。最初形成phlorin产物对于分离和表征N-苯基体系足够稳定，尽管相关的N-烷基菲林类似物稳定性较差。尝试用DDQ脱除中间的卟啉导致分解，但是N-烷基卟啉可以用0.2％的氯化铁水溶液氧化。尽管在这些条件下不能取代苯基取代的发氯林，但经氯仿处理后确实提供了吡唑并卟啉醋酸银在酸性条件下。与氧化醋酸银 也有 氧绿蛋白在5-位选择性地形成氧键的类似物。含吡唑卟啉类似物是交叉共轭的，仅表现出少量的变径性。观察到内部CH共振在5.27和5.87 ppm之间，而外部中观质子在6.84–7.88 ppm范围内。总体芳香特性的临界点归因于偶极共振的贡献者。质子化极大地增加了变质性，并由此形成了双质子化的指示。卟啉类似物在2.65–3

  DOI：

  10.1039/c1ob05603d

文献信息

• Adding to the confusion! Synthesis and metalation of pyrazole analogues of the porphyrins
  作者：Timothy D. Lash、Alexandra M. Young、Amber L. Von Ruden、Gregory M. Ferrence

  DOI：10.1039/b816057k

  日期：——

  N-substituted pyrazole dialdehydes are shown to react with a tripyrrane under '3 + 1' conditions to give aza-analogues of the N-confused porphyrins; these novel porphyrinoids show borderline aromatic properties and readily afford organometallic derivatives with Ni(OAc)2 and Pd(OAc)2.

  N-取代的吡唑二醛在“ 3 + 1”条件下与三吡喃发生反应，生成氮稠合的卟啉的氮杂类似物。这些新颖的卟啉类化合物显示出临界的芳族性质，并容易获得具有Ni（OAc）2和Pd（OAc）2的有机金属衍生物。
• 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.
• Pyrazole analogues of porphyrins and oxophlorins
  作者：Alexandra M. Young、Amber L. Von Ruden、Timothy D. Lash

  DOI：10.1039/c1ob05603d

  日期：——

  acetate under acidic conditions. Oxidations with silver acetate also afforded oxophlorin analogues where the oxo-linkage was selectively formed at the 5-position. The pyrazole-containing porphyrin analogues are cross-conjugated and exhibit only a small degree of diatropic character. The internal CH resonances were observed between 5.27 and 5.87 ppm, while the external meso-protons fell into a range of 6

  一系列 卟啉已经合成了具有吡唑环取代了通常的吡咯亚基之一的类似物。这是通过在TFA存在下使1-苯基，1-甲基和1-乙基吡唑-1,3-二甲醛与三吡喃反应，然后进行氧化步骤来实现的。最初形成phlorin产物对于分离和表征N-苯基体系足够稳定，尽管相关的N-烷基菲林类似物稳定性较差。尝试用DDQ脱除中间的卟啉导致分解，但是N-烷基卟啉可以用0.2％的氯化铁水溶液氧化。尽管在这些条件下不能取代苯基取代的发氯林，但经氯仿处理后确实提供了吡唑并卟啉醋酸银在酸性条件下。与氧化醋酸银 也有 氧绿蛋白在5-位选择性地形成氧键的类似物。含吡唑卟啉类似物是交叉共轭的，仅表现出少量的变径性。观察到内部CH共振在5.27和5.87 ppm之间，而外部中观质子在6.84–7.88 ppm范围内。总体芳香特性的临界点归因于偶极共振的贡献者。质子化极大地增加了变质性，并由此形成了双质子化的指示。卟啉类似物在2.65–3
• 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.