1-[4-(methylthio)phenyl]pyrazole | 572912-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-(methylthio)phenyl]pyrazole
• 英文别名: 1-(4-methylsulfanylphenyl)pyrazole
• CAS: 572912-93-7
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: BMBOBAYGFJUELG-UHFFFAOYSA-N

物化性质

• 沸点：
  306.8±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(methylthio)phenyl]pyrazole 在 Oxone 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 9.0h， 生成 1-[4-(methylsulfonyl)phenyl]pyrazole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring

  摘要：

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01448-4
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 、 4-甲硫基苯肼盐酸盐 以 乙醇 为溶剂， 反应 2.0h， 以54%的产率得到1-[4-(methylthio)phenyl]pyrazole
  参考文献：
  名称：

  Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring

  摘要：

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01448-4

文献信息

• Palladium-Catalyzed <i>ipso</i>-Borylation of Aryl Sulfides with Diborons
  作者：M. Bhanuchandra、Alexandre Baralle、Shinya Otsuka、Keisuke Nogi、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1021/acs.orglett.6b01305

  日期：2016.6.17

  ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C–S bonds into C–B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation

  一种催化宫浦型本位与二硼试剂芳基硫化物的-borylation已经实现，从而提供合成的使用arylboronate酯。将本来就不愿意的C–S键转换为C–B键的关键条件包括钯-NHC（N-杂环卡宾）预催化剂，双（频哪醇）二硼和六甲基二硅叠氮化锂。该协议适用于合理范围的芳基烷基硫化物。在二苯硫醚的反应中观察到双重硼化。
• Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring
  作者：Aldo Balsamo、Isabella Coletta、Angelo Guglielmotti、Carla Landolfi、Francesca Mancini、Adriano Martinelli、Claudio Milanese、Filippo Minutolo、Susanna Nencetti、Elisabetta Orlandini、Mario Pinza、Simona Rapposelli、Armando Rossello

  DOI：10.1016/s0223-5234(02)01448-4

  日期：2003.2

  Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory properties of these kinds of molecules. Among the compounds tested, only the 3-(p-methylsulfonylphenyl) substituted thiophene derivatives 17 and 22, showed a certain COX-2 inhibitory activity, accompanied by an appreciable COX-2 versus COX-1 selectivity. Only one of the 1-(p-methylsulfonylphenyl)pyrazole compounds (16) displayed a modest inhibitory activity towards both type of isoenzymes. while the pyrazole 1-(p-aminosulfonylphenyl) substituted 12 proved to be significantly active only towards COX-1. All the isoxazole derivatives were inactive on both COX isoforms. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.