5-hydroxy-3-methyl-5-phenyl-1-(2-thiophenecarboxylic)-pyrazoline | 915917-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-hydroxy-3-methyl-5-phenyl-1-(2-thiophenecarboxylic)-pyrazoline
• 英文别名: 1-(thiophen-2-ylcarbonyl)-3-methyl-5-phenyl-5-hydroxypyrazoline；[(5S)-5-hydroxy-3-methyl-5-phenyl-4H-pyrazol-1-yl]-thiophen-2-ylmethanone
• CAS: 915917-55-4
• 化学式: C₁₅H₁₄N₂O₂S
• 分子量: 286.354
• InChiKey: CTWOMUGDGGQCRJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-methyl-5-phenyl-1-(2-thiophenecarboxylic)-pyrazoline 、 二苯基二氯化锡 以78%的产率得到Ph2Sn(5-hydroxy-3-methyl-5-phenyl-1-(2-thiophenecarboxylic)pyrazoline(2-))
  参考文献：
  名称：

  含有 5-羟基吡唑啉衍生物作为配体的五配位二有机锡 (IV) 配合物的合成、光谱表征和 X 射线结构

  摘要：

  摘要 由 R 2 SnCl 2 (R = Me, Ph) 与配体 5-hydroxy-3-metyl-5-phenyl-1-( S-benzildithiocarbazate)-pyrazoline (H 2 L 1 )和5-羟基-3-甲基-5-苯基-1-(2-噻吩羧酸)-吡唑啉(H 2 L 2 )。通过元素分析、IR、 1 H、 13 C、 119 Sn NMR 和 Mossbauer 光谱对配合物进行表征。还对配合物[Me 2 SnL 1 ]、[Ph 2 SnL 1 ] 和[Me 2 SnL 2 ] 进行了单晶X 射线衍射研究，结果表明配合物的Sn(IV)中心原子采用畸变三角双锥 (TBP) 几何结构，具有 ONX-三齿 (X = O 和 S) 配体的 N 原子和两个占据赤道位点的有机基团。[Me 2 Sn(L 1 )] 和 [Ph 2 Sn(L 1 )] 的 C-Sn-C 角是使用基于点电荷模型的

  DOI：

  10.1016/j.molstruc.2010.07.023
• 作为产物：
  描述：

  2-噻吩甲酰肼 、 1-苯基-1,3-丁二酮 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到5-hydroxy-3-methyl-5-phenyl-1-(2-thiophenecarboxylic)-pyrazoline
  参考文献：
  名称：

  Synthesis, Spectroscopic Studies and X-ray Crystal Structures of New Pyrazoline and Pyrazole Derivatives

  摘要：

  一些 1,3-二酮与肼衍生物的吡唑啉化合物的合成与表征，即 1-(S-苄基二硫代卡巴肼)-3-甲基-5-苯基-5-羟基吡唑啉 (1)；1-(2-噻吩羧基)-3-甲基-5-苯基-5-羟基吡唑啉 (2)；1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6).通过红外光谱、(1H, 13C)-NMR光谱和单晶X射线衍射研究发现，化合物(1)、(2)和(3)是以吡唑啉的形式形成的，而(4)和(5)只有在酸性条件下才形成吡唑衍生物。化合物（1）以正交 P212121 结晶，a = 6.38960(10) 埃，b = 12.9176(3) Å, c = 21.2552(5) Å, (2) 结晶为单斜晶系，P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) 结晶为单斜晶系，C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) 结晶为单斜晶系，P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å.(3)衍生物是第一个由 2,4-戊二酮制备并具有晶体学特征的吡唑啉化合物。一些 1,3-二酮与肼衍生物的吡唑啉化合物的合成和表征，即 1-(S-苄基二硫代氨基甲酸酯)-3-甲基-5-苯基-5-羟基吡唑啉 (1)；1-(2-噻吩羧基)-3-甲基-5-苯基-5-羟基吡唑啉 (2)；1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6).通过红外光谱、(1H, 13C)-NMR光谱和单晶X射线衍射研究发现，化合物(1)、(2)和(3)是以吡唑啉的形式形成的，而(4)和(5)只有在酸性条件下才形成吡唑衍生物。化合物（1）以正交 P212121 结晶，a = 6.38960(10) 埃，b = 12.9176(3) Å, c = 21.2552(5) Å, (2) 结晶为单斜晶系，P21/n, a = 11.3617(2) 埃，b = 8.4988(2) 埃，c = 92.8900(10) 埃和β = 92.8900(5)°，（3）结晶为单斜晶系，C2/c，a = 15.9500(5) 埃，b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) 结晶为单斜晶系，P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å.(3)衍生物是第一个由 2,4-戊二酮制备并具有晶体学特征的吡唑啉化合物。

  DOI：

  10.1007/s10870-010-9896-2

文献信息

• Synthesis, Spectroscopic Studies and X-ray Crystal Structures of New Pyrazoline and Pyrazole Derivatives
  作者：Gerimário F. de Sousa、Claudia C. Gatto、Inês S. Resck、Victor M. Deflon

  DOI：10.1007/s10870-010-9896-2

  日期：2011.3

  The synthesis and characterization of some pyrazoline compounds of 1,3-diketones with hydrazine derivatives, namely, 1-(S-benzyldithiocarbazate)-3-methyl-5-phenyl-5-hydroxypyrazoline (1); 1-(2-thiophenecarboxylic)-3-methyl-5-phenyl-5-hydroxypyrazoline (2); 1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6) are reported. Studies by IR, (1H, 13C)-NMR spectroscopies and single crystal X-ray diffraction revealed that compounds (1), (2) and (3) are formed as pyrazoline, whereas (4) and (5) are formed as pyrazole derivatives only under acidic conditions. Compound (1) crystallizes in orthorhombic P212121, a = 6.38960(10) Å, b = 12.9176(3) Å, c = 21.2552(5) Å, (2) crystallizes in monoclinic, P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) crystallizes in monoclinic, C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) crystallizes in monoclinic, P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å. The (3) derivative represents the first pyrazoline compound prepared from 2,4-pentanedione and characterized crystallographically. The synthesis and characterization of some pyrazoline compounds of 1,3-diketones with hydrazine derivatives, namely, 1-(S-benzyldithiocarbazate)-3-methyl-5-phenyl-5-hydroxypyrazoline (1); 1-(2-thiophenecarboxylic)-3-methyl-5-phenyl-5-hydroxypyrazoline (2); 1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6) are reported. Studies by IR, (1H, 13C)-NMR spectroscopies and single crystal X-ray diffraction revealed that compounds (1), (2) and (3) are formed as pyrazoline, whereas (4) and (5) are formed as pyrazole derivatives only under acidic conditions. Compound (1) crystallizes in orthorhombic P212121, a = 6.38960(10) Å, b = 12.9176(3) Å, c = 21.2552(5) Å, (2) crystallizes in monoclinic, P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) crystallizes in monoclinic, C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) crystallizes in monoclinic, P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å. The (3) derivative represents the first pyrazoline compound prepared from 2,4-pentanedione and characterized crystallographically.

  一些 1,3-二酮与肼衍生物的吡唑啉化合物的合成与表征，即 1-(S-苄基二硫代卡巴肼)-3-甲基-5-苯基-5-羟基吡唑啉 (1)；1-(2-噻吩羧基)-3-甲基-5-苯基-5-羟基吡唑啉 (2)；1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6).通过红外光谱、(1H, 13C)-NMR光谱和单晶X射线衍射研究发现，化合物(1)、(2)和(3)是以吡唑啉的形式形成的，而(4)和(5)只有在酸性条件下才形成吡唑衍生物。化合物（1）以正交 P212121 结晶，a = 6.38960(10) 埃，b = 12.9176(3) Å, c = 21.2552(5) Å, (2) 结晶为单斜晶系，P21/n, a = 11.3617(2) Å, b = 8.4988(2) Å, c = 92.8900(10) Å and β = 92.8900(5)°, (3) 结晶为单斜晶系，C2/c, a = 15.9500(5) Å, b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) 结晶为单斜晶系，P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å.(3)衍生物是第一个由 2,4-戊二酮制备并具有晶体学特征的吡唑啉化合物。一些 1,3-二酮与肼衍生物的吡唑啉化合物的合成和表征，即 1-(S-苄基二硫代氨基甲酸酯)-3-甲基-5-苯基-5-羟基吡唑啉 (1)；1-(2-噻吩羧基)-3-甲基-5-苯基-5-羟基吡唑啉 (2)；1-(2-thiophenecarboxylic)-3,5-dimethyl-5-hydroxypyrazoline (3); 1-(S-benzyldithiocarbazato)-3-methyl-5-phenylpyrazole (4); 1-(2-thiophenecarboxylic)-3-methyl-5-phenylpyrazole (5) and 1-(S-benzyldithiocarbazate)-3,5-dimethylpyrazole (6).通过红外光谱、(1H, 13C)-NMR光谱和单晶X射线衍射研究发现，化合物(1)、(2)和(3)是以吡唑啉的形式形成的，而(4)和(5)只有在酸性条件下才形成吡唑衍生物。化合物（1）以正交 P212121 结晶，a = 6.38960(10) 埃，b = 12.9176(3) Å, c = 21.2552(5) Å, (2) 结晶为单斜晶系，P21/n, a = 11.3617(2) 埃，b = 8.4988(2) 埃，c = 92.8900(10) 埃和β = 92.8900(5)°，（3）结晶为单斜晶系，C2/c，a = 15.9500(5) 埃，b = 9.3766(3) Å, c = 16.6910(5) Å and β = 113.825(2)°, (4) 结晶为单斜晶系，P21/c, a = 15.228(4) Å, b = 5.5714(13) Å, c = 19.956(5) Å and β = 91.575(7)° and (6) crystallizes in orthorhombic, P212121, a = 5.3920(2) Å, b = 11.2074(5) Å, c = 21.885(1) Å.(3)衍生物是第一个由 2,4-戊二酮制备并具有晶体学特征的吡唑啉化合物。
• Synthesis, spectroscopic characterization and X-ray structures of five-coordinate diorganotin(IV) complexes containing 5-hydroxypyrazoline derivatives as ligands
  作者：Gerimário F. de Sousa、Edgardo Garcia、Claudia C. Gatto、Inês S. Resck、Victor M. Deflon、José D. Ardisson

  DOI：10.1016/j.molstruc.2010.07.023

  日期：2010.9

  2 SnL 1 ], [Ph 2 SnL 1 ] and [Me 2 SnL 2 ] were also studied by single crystal X-ray diffraction and the results showed that the Sn(IV) central atom of the complexes adopts a distorted trigonal bipyramidal (TBP) geometry with the N atom of the ONX-tridentate (X = O and S) ligand and two organic groups occupying equatorial sites. The C–Sn–C angles for [Me 2 Sn(L 1 )] and [Ph 2 Sn(L 1 )] were calculated

  摘要 由 R 2 SnCl 2 (R = Me, Ph) 与配体 5-hydroxy-3-metyl-5-phenyl-1-( S-benzildithiocarbazate)-pyrazoline (H 2 L 1 )和5-羟基-3-甲基-5-苯基-1-(2-噻吩羧酸)-吡唑啉(H 2 L 2 )。通过元素分析、IR、 1 H、 13 C、 119 Sn NMR 和 Mossbauer 光谱对配合物进行表征。还对配合物[Me 2 SnL 1 ]、[Ph 2 SnL 1 ] 和[Me 2 SnL 2 ] 进行了单晶X 射线衍射研究，结果表明配合物的Sn(IV)中心原子采用畸变三角双锥 (TBP) 几何结构，具有 ONX-三齿 (X = O 和 S) 配体的 N 原子和两个占据赤道位点的有机基团。[Me 2 Sn(L 1 )] 和 [Ph 2 Sn(L 1 )] 的 C-Sn-C 角是使用基于点电荷模型的