3,5-dimethyl-4-[(4-methylphenyl)diazenyl]-1H-pyrazole | 3656-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dimethyl-4-[(4-methylphenyl)diazenyl]-1H-pyrazole
• 英文别名: 3,5-dimethyl-4-(p-tolylazo)pyrazole；(3,5-dimethyl-1H-pyrazol-4-yl)-(4-methylphenyl)diazene
• CAS: 3656-06-2
• 化学式: C₁₂H₁₄N₄
• 分子量: 214.27
• InChiKey: UDGHOTLHRKJELE-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  419.9±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-4-[(4-methylphenyl)diazenyl]-1H-pyrazole 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 4-{3,5-dimethyl-4-[(4-methylphenyl)diazenyl]-1H-pyrazol-1-yl}butan-1-ol
  参考文献：
  名称：

  Synthesis of mycostatics based on 4-aryldiazenyl-3,5-dimethylpyrazoles

  摘要：

  3-芳基肼叉戊二酮与水合肼、2-羟基乙基肼、苄基肼盐酸盐和4-肼基苯磺酰胺盐酸盐缩合生成4-芳基偶氮-3,5-二甲基吡唑。合成N-取代的4-芳基偶氮吡唑的另一种途径是基于NH-吡唑与卤代烷的烷基化反应。合成的化合物对八种致病性皮肤真菌、念珠菌属酵母样真菌和淋病奈瑟菌进行了抗菌活性测试。结构-活性关系分析表明，在N(1)原子上带有H、AcO(CH2)4或HO(CH2)4取代基的4-甲苯基偶氮吡唑对所有研究中的皮肤真菌菌株具有最高的抑菌活性。然而，4-芳基偶氮-3,5-二甲基吡唑对McCoy B细胞系表现出相当大的细胞毒性。

  DOI：

  10.1007/s11172-021-3193-4
• 作为产物：
  描述：

  3-[(4-甲基苯基)二氮烯基]戊烷-2,4-二酮 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3,5-dimethyl-4-[(4-methylphenyl)diazenyl]-1H-pyrazole
  参考文献：
  名称：

  Non-natural nucleosides bearing 4-aryldiazenylpyrazole aglycone

  摘要：

  Ribosylation of 4-aryldiazenyl-3-R-5-R'-pyrazoles with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose in the presence of tin(IV) chloride gives alpha- and beta-anomeric N-(2,3,5-tri-O-acetylribofuranosyl)-substituted derivatives. Their HPLC separation and deacetylation (MeOH, MeONa) affords 1-(beta-D-ribofuranosyl)-3-R-5-R'-4-(aryldiazenyl)-1H-pyrazoles.

  DOI：

  10.1016/j.mencom.2016.03.006

文献信息

• Studies with Polyfunctionally Substituted Heterocycles: New Synthesis of Pyrido[5′, 4′:2,3][1,3,4]oxadiazolo[3,2-a]pyridine; Pyridazine; 1,3,4-Oxadiazote; and Pyrazolo[1,5-a]Pyrimidine Derivatives
  作者：Magda A. Barsy、Mohammed A. Elmaghraby、Salwa M. Ahmed

  DOI：10.1002/jccs.199800099

  日期：1998.10

  AbstractCyanoacetohydrazide 1a reacts with 2‐arylhydrazoketons 2a,b and 3a,b in refluxing ethanol to yield pyrido[5′,4′:2,3][1,3,4]oxadiazolo[3,2‐a]pyridine and pyridazine derivatives; in the absence of solvent pyrazolo[1,5‐a]pyrimidine derivatives were obtained. The reaction of 2a,b and 3a,b will) benzoylhydrazine afforded 1,3,4‐oxadiazole and pyrazole derivatives.
• Banditelli, Guido; Bandini, Anna Laura; Minghetti, Giovanni, Canadian Journal of Chemistry, 1981, vol. 59, p. 1241 - 1246
  作者：Banditelli, Guido、Bandini, Anna Laura、Minghetti, Giovanni、Bonati, Flavio

  DOI：——

  日期：——
• [EN] LIGHT-RESPONSIVE TEMPORARY ADHESIVES AND USE THEREOF<br/>[FR] ADHÉSIFS TEMPORAIRES SENSIBLES À LA LUMIÈRE ET LEUR UTILISATION
  申请人：UNIV BRANDEIS

  公开号：WO2020227226A1

  公开（公告）日：2020-11-12

  The invention relates to a device that includes a substrate and a thin film of a photo-switchable adhesive layer applied to at least one surface of the substrate. A method of releasably supporting a product that includes adhering a product onto the thin film of the device and exposing the thin film to light sufficient to cause a change in the adhesive strength of the thin film. A method of making the device is also disclosed.
• Synthesis of mycostatics based on 4-aryldiazenyl-3,5-dimethylpyrazoles
  作者：O. G. Khudina、A. E. Ivanova、Ya. V. Burgart、N. A. Gerasimova、N. P. Evstigneeva、V. I. Saloutin

  DOI：10.1007/s11172-021-3193-4

  日期：2021.6

  The condensation of 3-arylhydrazinylidenepentane-2,4-diones with hydrazine hydrate, 2-hydroxyethylhydrazine, benzylhydrazine hydrochloride, and 4-hydrazinylbenzenesulfonamide hydrochloride gave 4-aryldiazenyl-3,5-dimethylpyrazoles. An alternative route to the synthesis of N-substituted 4-aryldiazenylpyrazoles is based on the alkylation of NH-pyrazoles with haloalkanes. The synthesized compounds were tested for antimicrobial activity against eight pathogenic dermatophytes, yeast-like fungi of the Candida genus and the bacteria Neisseria gonorrhoeae. The structure—activity relationship analysis showed that 4-tolyldiazenylpyrazoles bearing H, AcO(CH2)4, or HO(CH2)4 substituents at the N(1) atom have the highest mycostatic activity against all the dermatophyte strains under study. However, 4-aryldiazenyl-3,5-dimethylpyrazoles proved to be quite cytotoxic against the McCoy B cell line.

  3-芳基肼叉戊二酮与水合肼、2-羟基乙基肼、苄基肼盐酸盐和4-肼基苯磺酰胺盐酸盐缩合生成4-芳基偶氮-3,5-二甲基吡唑。合成N-取代的4-芳基偶氮吡唑的另一种途径是基于NH-吡唑与卤代烷的烷基化反应。合成的化合物对八种致病性皮肤真菌、念珠菌属酵母样真菌和淋病奈瑟菌进行了抗菌活性测试。结构-活性关系分析表明，在N(1)原子上带有H、AcO(CH2)4或HO(CH2)4取代基的4-甲苯基偶氮吡唑对所有研究中的皮肤真菌菌株具有最高的抑菌活性。然而，4-芳基偶氮-3,5-二甲基吡唑对McCoy B细胞系表现出相当大的细胞毒性。
• Non-natural nucleosides bearing 4-aryldiazenylpyrazole aglycone
  作者：Anna E. Ivanova、Yanina V. Burgart、Viktor I. Saloutin

  DOI：10.1016/j.mencom.2016.03.006

  日期：2016.3

  Ribosylation of 4-aryldiazenyl-3-R-5-R'-pyrazoles with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose in the presence of tin(IV) chloride gives alpha- and beta-anomeric N-(2,3,5-tri-O-acetylribofuranosyl)-substituted derivatives. Their HPLC separation and deacetylation (MeOH, MeONa) affords 1-(beta-D-ribofuranosyl)-3-R-5-R'-4-(aryldiazenyl)-1H-pyrazoles.