4-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine | 62538-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine
• 英文别名: 4-(3-chlorophenyl)-5-methyl-1H-pyrazol-3-amine
• CAS: 62538-18-5
• 化学式: C₁₀H₁₀ClN₃
• mdl: MFCD09438994
• 分子量: 207.662
• InChiKey: HOORSUWNFBFXET-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±42.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-Benzyl-4-chloro-2,2-dioxo-2lambda6,1-benzothiazine-3-carbaldehyde 、 4-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以60%的产率得到8-Benzyl-15-(3-chlorophenyl)-14-methyl-9lambda6-thia-8,12,13,17-tetrazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),2,4,6,10,13,15-heptaene 9,9-dioxide
  参考文献：
  名称：

  β-氯醛与ncn双亲核试剂的反应选择性合成嘧啶并[5,4-c] [2,1]苯并噻嗪

  摘要：

  描述了基于苯并噻嗪的氯醛衍生物与am的反应在嘧啶环的[ c ]侧进行嘧啶环稠合的方法。研究了反应产物的结构异构体的形成，并显示了杂环化反应的区域选择性。合成了许多新颖的嘧啶并苯并噻嗪。J.杂环化​​学.2010。

  DOI：

  10.1002/jhet.271
• 作为产物：
  描述：

  间氯氰苄 在 盐酸肼 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 0.08h， 生成 4-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine
  参考文献：
  名称：

  N-Acetyl-3-aminopyrazoles block the non-canonical NF-kB cascade by selectively inhibiting NIK

  摘要：

  由于击中导向优化，氨基吡唑3a是一种选择性超过44种激酶的NIK抑制剂。

  DOI：

  10.1039/c8md00068a

文献信息

• Pyrazole-3(5)-diazonium salts in the synthesis of novel pyrazolo[5,1-c][1,2,4]triazines
  作者：Kh. S. Shikhaliev、V. V. Didenko、V. A. Voronkova、D. V. Kryl’skii

  DOI：10.1007/s11172-009-0132-1

  日期：2009.5

  Coupling of pyrazole-3(5)-diazonium salts with cyclic 1,3-dicarbonyl (active methylene) compounds followed by cyclocondensation of the resulting hetarylhydrazones gave novel pyrazolo[5,1-c][1,2,4]triazines.

  将吡唑-3(5)-重氮盐与环状1,3-二羰基（活性亚甲基）化合物偶联，然后将所得杂芳基腙环缩合，得到新型吡唑并[5,1-c][1,2,4]三嗪。
• Chemospecific reactions of as-triazine ring reduction in sulfonyl derivatives of pyrazolo[5,1-c][1,2,4]triazines
  作者：Irina V. Ledenyova、Pavel A. Kartavtsev、Khidmet S. Shikhaliev、Alevtina Yu. Egorova

  DOI：10.1007/s10593-017-2183-9

  日期：2017.10

  describes the reduction of 4-methyl- and 4-phenyl-3-(methylsulfonyl)pyrazolo[5,1-c][1,2,4]triazines and 3-[(4-methylphenyl)sulfonyl]pyrazolo[5,1-c][1,2,4]triazines, which were obtained by reactions of pyrazole-3(5)-diazonium salts with the appropriate β-ketosulfones. The interaction of sulfonyl derivatives of pyrazolo[5,1-c][1,2,4]triazines with sodium dithionite or thiourea 1,1-dioxide under mild conditions

  这项研究描述了4-甲基和4-苯基-3-（甲基磺酰基）吡唑并[5,1- c ] [1,2,4]三嗪和3-[（4-甲基苯基）磺酰基]吡唑并[5]的还原，1- c ] [1,2,4]三嗪，是通过吡唑-3（5）-重氮盐与适当的β-酮砜反应制得的。吡唑并衍生物磺酰的相互作用[5,1- c ^ ] [1,2,4]用连二亚硫酸钠或温和的条件下的硫脲1,1-二氧化物三嗪导致的chemospecific部分还原为三嗪环。通过X射线结构分析建立了所获得的吡唑并[5，1- c ] [1,2,4]三嗪二氢衍生物的构型。
• 10.1007/s11172-024-4257-z
  作者：Sukhanova、Prezent、Fakhrutdinov、Zavarzin

  DOI：10.1007/s11172-024-4257-z

  日期：——

  An efficient synthetic approach based on the chelate methodology and difluoroboron complexes was developed for estrone derivatives containing pyrazolo[1,5-a]pyrimidine substituents at the side chain of ring A.

  开发了一种基于螯合方法和二氟硼络合物的有效合成方法，用于合成 A 环侧链含有吡唑并[1,5-a]嘧啶取代基的雌酮衍生物。
• Structure and tautomerism of 4-substituted 3(5)-aminopyrazoles in solution and in the solid state: NMR study and Ab initio calculations
  作者：E. E. Emelina、A. A. Petrov、D. V. Filyukov

  DOI：10.1134/s1070428014030191

  日期：2014.3

  Annular tautomerism of 3(5)-aminopyrazoles containing a cyano, thiocyanato, or aryl substituent in the 4-position has been studied by H-1 and C-13 NMR in solution, cross-polarization and magic-angle spinning C-13 NMR in the solid state, and ab initio quantum chemical calculations (B3LYP/6-31G**). The title compounds in the solid state exist as 3-amino tautomers. A rare case of slow (on the NMR time scale) annular prototropic tautomerism has been observed in DMSO-d (6): signals of particular tautomers (3- and 5-aminopyrazoles) have been detected in the NMR spectra. 4-Cyano and 4-thiocyanato derivatives exist preferentially as 5-amino tautomers, whereas 4-methoxy analog is represented mainly by the 3-amino tautomers. Ab initio calculations (B3LYP/6-31G**) for the gas phase and DMSO solution (in terms of the polarizable continuum model) have shown increase of the relative stability of more polar 5-amino tautomer in going to DMSO.
• Regioselective synthesis of pyrimido[5,4-c][2,1]benzothiazines by reactions of β-chloroaldehydes with n-c-n binucleophiles
  作者：Kirill Popov、Tatyana Volovnenko、Alexander Turov、Yulian Volovenko

  DOI：10.1002/jhet.271

  日期：——

  The method of pyrimidine ring fusion at the [c] side of benzothiazines based on the reaction of their chloroaldehyde derivatives with amidines is described. Formation of the structural isomers of reaction products was investigated, and regioselectivity of heterocyclization reactions was shown. A number of novel pyrimidobenzothiazines were synthesized. J. Heterocyclic Chem., 2010.

  描述了基于苯并噻嗪的氯醛衍生物与am的反应在嘧啶环的[ c ]侧进行嘧啶环稠合的方法。研究了反应产物的结构异构体的形成，并显示了杂环化反应的区域选择性。合成了许多新颖的嘧啶并苯并噻嗪。J.杂环化​​学.2010。