4-碘-1-甲基-1H-吡唑-3-羧酸 | 6647-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-碘-1-甲基-1H-吡唑-3-羧酸
• 中文别名: 4-碘代-1-甲基-吡唑-3-羧酸；4-碘-1-甲基吡唑-3-羧酸
• 英文名称: 4-iodo-1-methylpyrazole-3-carboxylic acid
• 英文别名: 4-iodo-1-methyl-1H-pyrazole-3-carboxylic acid
• CAS: 6647-98-9
• 化学式: C₅H₅IN₂O₂
• mdl: MFCD00465278
• 分子量: 252.011
• InChiKey: UQPXGRAYQOWZOD-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C
• 沸点：
  362.2±27.0 °C(Predicted)
• 密度：
  2.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-碘-1-甲基-1H-吡唑-3-羧酸 在 硫酸 、 硝酸 作用下， 反应 6.0h， 以58.3%的产率得到1-甲基-4-硝基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  Nitrodeiodination of 4-iodo-l-methylpyrazoles

  摘要：

  4-Iodo-1-methylpyrazoles react with a nitrating mixture at 55 degrees C to give the corresponding 4-nitro-1-methylpyrazoles. The qualitative dependence of the nitrodeiodination rate on the structure of the heterocycles and the reaction conditions was considered.

  DOI：

  10.1007/bf01431120
• 作为产物：
  描述：

  4-碘-1,3-二甲基吡唑 在 potassium permanganate 作用下， 以 水 为溶剂， 以26.6%的产率得到4-碘-1-甲基-1H-吡唑-3-羧酸
  参考文献：
  名称：

  Manaev, Yu. A.; Andreeva, M. A.; Perevalov, V. P., Journal of general chemistry of the USSR, 1982, vol. 52, # 11, p. 2291 - 2296

  摘要：

  DOI：

文献信息

• New approach to electrochemical iodination of arenes exemplified by the synthesis of 4-iodopyrazoles of different structures
  作者：B. V. Lyalin、V. A. Petrosyan

  DOI：10.1007/s11172-014-0438-5

  日期：2014.2

  The two-stage electrosynthesis of 4-iodosubstituted pyrazole derivatives was performed. At the first stage, KIO3 was obtained at the Ni anode under the undivided galvanostatic conditions of electrolysis of an aqueous alkaline solution of KI (or I2) at the Ni anode. At the second stage, pyrazole and its derivatives were iodinated in the heterophase (H2O-CHCl3 (CCl4)) medium by the KIO3-KI (or KIO3-I2) system in the presence of H2SO4. The yields of iodopyrazoles were 74–92%. The electrochemical iodination of anisole, 2-methylpyrazole, and thiophene was carried out to form 4-iodoanisole (88% yield), 4,5-diiodo-2-methylimidazole (54% yield), and a mixture of 2-iodothiophene (60% yield) and 2,5-diiodothiophene (4% yield).

  进行了4-碘代吡唑衍生物的两阶段电合成。在第一阶段，在镍阳极上通过镍阳极在水溶液碱性KI（或I2）溶液的未分隔恒电流电解条件下获得KIO3。在第二阶段，在硫酸存在下，通过KIO3-KI（或KIO3-I2）体系在异相（H2O-CHCl3（CCl4））介质中碘化吡唑及其衍生物。碘吡唑的产率为74-92%。进行了茴香醚、2-甲基吡唑和噻吩的电化学碘化反应，合成了4-碘茴香醚（产率88%）、4,5-二碘-2-甲基咪唑（产率54%）以及2-碘噻吩（产率60%）和2,5-二碘噻吩（产率4%）的混合物。
• Efficient iodination of structurally varying pyrazoles in heterophase medium
  作者：B. V. Lyalin、V. A. Petrosyan

  DOI：10.1007/s11172-013-0140-z

  日期：2013.4

  A synthesis of 4-iodo-substituted pyrazoles by iodination of pyrazole and its derivatives in the heterophase (H2O/CHCl3 (CCl4)) medium with the system KI-KIO3 in the presence of H2SO4 additives was accomplished. The yields of 4-iodo-substituted pyrazoles in the iodination of pyrazole, 3,5-dimethylpyrazole, pyrazole-3(5)-carboxylic acid, 1-methylpyrazole-3-carboxylic acid, 1-methylpyrazole-5-carboxylic acid, 3-nitropyrazole, 1-methyl-3-nitropyrazole, 1-methylpyrazole, 1-ethylpyrazole, and 1-isopropylpyrazole were within 80–97%, whereas in the case of 3-nitropyrazole-5-carboxylic acid it was 32%.

  通过在异相（H2O/CHCl3 (CCl4)）介质中，使用KI-KIO3体系和H2SO4添加剂对吡唑及其衍生物进行碘化，成功合成了4-碘取代的吡唑。吡唑、3,5-二甲基吡唑、吡唑-3(5)-羧酸、1-甲基吡唑-3-羧酸、1-甲基吡唑-5-羧酸、3-硝基吡唑、1-甲基-3-硝基吡唑、1-甲基吡唑、1-乙基吡唑和1-异丙基吡唑的4-碘取代吡唑的产率在80%至97%之间，而3-硝基吡唑-5-羧酸的产率为32%。
• [EN] HALO-SUBSTITUTED PIPERIDINES AS OREXIN RECEPTOR MODULATORS<br/>[FR] PIPÉRIDINES HALOSUBSTITUÉES EN TANT QUE MODULATEURS DE RÉCEPTEUR DES OREXINES
  申请人：ASTRAZENECA AB

  公开号：WO2017139603A1

  公开（公告）日：2017-08-17

  The present application relates to certain halo-substituted piperidine compounds, pharmaceutical compositions containing them, and methods of using them, including methods for treating substance addiction, panic disorder, anxiety, post-traumatic stress disorder, pain, depression, seasonal affective disorder, an eating disorder, or hypertension.

  本申请涉及某些含卤代哌啶化合物、含有它们的药物组合物，以及使用它们的方法，包括用于治疗物质成瘾、恐慌障碍、焦虑、创伤后应激障碍、疼痛、抑郁、季节性情感障碍、进食障碍或高血压的方法。
• Oxidative iodination of substituted N-methylpyrazoles
  作者：S. F. Vasilevskii、M. S. Shvartsberg

  DOI：10.1007/bf00949685

  日期：1980.5
• Synthesis, SAR study, and biological evaluation of novel quinoline derivatives as phosphodiesterase 10A inhibitors with reduced CYP3A4 inhibition
  作者：Wataru Hamaguchi、Naoyuki Masuda、Satoshi Miyamoto、Yasuhiro Shiina、Shigetoshi Kikuchi、Takuma Mihara、Hiroyuki Moriguchi、Hiroshi Fushiki、Yoshihiro Murakami、Yasushi Amano、Kazuya Honbou、Kouji Hattori

  DOI：10.1016/j.bmc.2014.11.039

  日期：2015.1

  A novel class of phosphodiesterase 10A inhibitors with potent PDE10A inhibitory activity and reduced CYP3A4 inhibition was designed and synthesized starting from 2-[4-([1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl] oxy} methyl) phenyl] quinoline (1). Replacement of pyridine ring of 1 with N-methyl pyridone ring drastically improved CYP3A4 inhibition, and further optimization of these quinoline analogues identified 1-methyl-5-(1-methyl-3-[4-(quinolin-2-yl) phenoxy] methyl}-1H-pyrazol-4-yl) pyridin-2(1H)-one (42b), which showed potent PDE10A inhibitory activity and a good CYP3A4 inhibition profile. A PET study with C-11-labeled 42b indicated that 42b exhibited good brain penetration and specifically accumulated in the rodent striatum. Further, oral administration of 42b dose-dependently attenuated phencyclidine-induced hyperlocomotion in mice with an ED50 value of 2.0 mg/kg and improved visual-recognition memory impairment at 0.1 and 0.3 mg/kg in mice novel object recognition test. (C) 2014 Elsevier Ltd. All rights reserved.