4-chloro-3(5)-phenyl-1H-pyrazole | 59843-36-6

• 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-chloro-3(5)-phenyl-1H-pyrazole
• 英文别名: 4-chloro-3-phenyl-1H-pyrazole；3-Phenyl-4-chlor-pyrazol；3-phenyl-4-chloro-1H-pyrazole；4-chloro-3-phenyl-1(2)H-pyrazole；4-Chlor-3-phenyl-1(2)H-pyrazol；4-chloro-3-phenyl-pyrazole；4-chloro-5-phenyl-1H-pyrazole
• CAS: 59843-36-6
• 化学式: C₉H₇ClN₂
• 分子量: 178.621
• InChiKey: IOUPHQSPQSPNIO-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  329.4±22.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-3(5)-phenyl-1H-pyrazole 、 氯甲酸甲酯 生成 4-chloro-3-phenyl-pyrazole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  v. Auwers; Breyhan, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 143, p. 259,273

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基吡唑 在 Oxone 、 sodium chloride 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 以77%的产率得到4-chloro-3(5)-phenyl-1H-pyrazole
  参考文献：
  名称：

  使用卤化钠盐和Oxone对吡唑进行温和卤化

  摘要：

  报道了一种温和，廉价且操作简单的吡唑卤化方法，该方法利用了Oxone和卤化钠盐。这项工作记录了烷基，芳基，烯丙基和苄基取代的4-氯和4-溴吡唑的17个实例，收率高达93％。反应在环境条件下在水中进行，避免了有机副产物的产生。

  DOI：

  10.1016/j.tetlet.2017.09.042

文献信息

• Oxidative Photochlorination of Electron‐Rich Arenes via in situ Bromination
  作者：Simon Josef Siegfried Düsel、Burkhard König

  DOI：10.1002/ejoc.201900411

  日期：2020.3.15

  Electron rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible‐light and 4CzIPN as organic photoredox catalyst. The substrates are in situ brominated in a first photoredox‐catalyzed oxidation step, followed by a photocatalyzed ipso‐chlorination yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient

  在催化量的溴离子、可见光和 4CzIPN 作为有机光氧化还原催化剂的存在下，富电子芳烃被氧化光氯化。底物在第一个光氧化还原催化氧化步骤中原位溴化，然后进行光催化同氯化，产生具有高邻位/对位区域选择性的目标化合物。双氧是一种绿色方便的末端氧化剂。盐酸水溶液作为氯化物源，减少了含盐副产品的数量。
• Pyrazole amides
  申请人：The Upjohn Company

  公开号：US04072498A1

  公开（公告）日：1978-02-07

  The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.

  本发明公开了取代吡唑基的酰胺和硫代酰胺，其在α或β位置上取代，可用作除草剂。
• CARBOXAMIDE COMPOUNDS AND THEIR USE AS CALPAIN INHIBITORS V
  申请人：Kling Andreas

  公开号：US20110152265A1

  公开（公告）日：2011-06-23

  The present invention relates to novel carboxamide compounds and their use for the manufacture of a medicament. The carboxamide compounds are inhibitors of calpain (calcium dependant cysteine proteases). The invention therefore also relates to the use of these carboxamide compounds for treating a disorder associated with an elevated calpain activity. The carboxamide compounds are compounds of the general formula I in which R 1 , R 2 , R 3 R 4 , R 5 , m and n have the meanings mentioned in the claims and the description, the tautomers thereof, the hydrates thereof and the pharmaceutically suitable salts thereof. Of these compounds those are preferred wherein R 1 is optionally substituted phenyl-C 1 -C 2 -alkyl or hetaryl-C 1 -C 2 -alkyl, R 2 is optionally substituted aryl, hetaryl, aryl-C 1 -C 6 -alkyl, aryl-C 2 -C 6 -alkenyl or hetaryl-C 1 -C 4 -alkyl, R 3 is C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl, or phenyl-C 1 -C 3 -alkyl, R 4 and R 5 independently of one another are halogen, CF 3 , CHF 2 , CH 2 F, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy, and m and n independently of one another are 0 or 1.

  本发明涉及新型羧酰胺化合物及其用于制备药物的用途。这些羧酰胺化合物是钙依赖性半胱氨酸蛋白酶（calpain）的抑制剂。因此，本发明还涉及使用这些羧酰胺化合物用于治疗与升高的calpain活性相关的疾病。这些羧酰胺化合物是通式I的化合物，其中R1、R2、R3、R4、R5、m和n在权利要求书和说明书中提到了它们的含义，它们的互变异构体，水合物和药学上适宜的盐。其中，偏好使用R1为可选取代的苯基-C1-C2-烷基或杂环基-C1-C2-烷基，R2为可选取代的芳基，杂环基，芳基-C1-C6-烷基，芳基-C2-C6-烯基或杂环基-C1-C4-烷基，R3为C1-C3-烷基，C1-C3-卤代烷基，C2-C4-烯基，C3-C6-环烷基，C3-C6-环烷基-C1-C2-烷基或苯基-C1-C3-烷基，R4和R5各自独立地是卤素，CF3，CHF2，CH2F，C1-C2-烷基或C1-C2-烷氧基，而m和n各自独立地为0或1。
• Carboxamide compounds and their use as calpain inhibitors V
  申请人：Kling Andreas

  公开号：US09051304B2

  公开（公告）日：2015-06-09

  The present invention relates to novel carboxamide compounds and their use for the manufacture of a medicament. The carboxamide compounds are inhibitors of calpain (calcium dependant cysteine proteases). The invention therefore also relates to the use of these carboxamide compounds for treating a disorder associated with an elevated calpain activity. The carboxamide compounds are compounds of the general formula I in which R1, R2, R3 R4, R5, m and n have the meanings mentioned in the claims and the description, the tautomers thereof, the hydrates thereof and the pharmaceutically suitable salts thereof. Of these compounds those are preferred wherein R1 is optionally substituted phenyl-C1-C2-alkyl or hetaryl-C1-C2-alkyl, R2 is optionally substituted aryl, hetaryl, aryl-C1-C6-alkyl, aryl-C2-C6-alkenyl or hetaryl-C1-C4-alkyl, R3 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, or phenyl-C1-C3-alkyl, R4 and R5 independently of one another are halogen, CF3, CHF2, CH2F, C1-C2-alkyl or C1-C2-alkoxy, and m and n independently of one another are 0 or 1.

  本发明涉及新型羧酰胺化合物及其用于制备药物的用途。这些羧酰胺化合物是钙依赖性半胱氨酸蛋白酶(calpain)的抑制剂。因此，本发明还涉及使用这些羧酰胺化合物治疗与升高的calpain活性有关的疾病。这些羧酰胺化合物是通式I的化合物，在其中R1、R2、R3、R4、R5、m和n具有所述权利要求和描述中提到的含义，它们的互变异构体、水合物和药学上适宜的盐也属于本发明的保护范围。其中，偏好使用R1为可选取代的苯基-C1-C2-烷基或杂环基-C1-C2-烷基，R2为可选取代的芳基、杂环基、芳基-C1-C6-烷基、芳基-C2-C6-烯基或杂环基-C1-C4-烷基，R3为C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C3-C6-环烷基、C3-C6-环烷基-C1-C2-烷基或苯基-C1-C3-烷基，R4和R5各自独立地为卤素、CF3、CHF2、CH2F、C1-C2-烷基或C1-C2-烷氧基，m和n各自独立地为0或1。
• The interplay of hydrogen bonds and halogen bonds in the structure of NH-pyrazoles bearing C-aryl and C-halogen substituents
  作者：M. Ángeles García、Pilar Cabildo、Rosa M. Claramunt、Elena Pinilla、M. Rosario Torres、Ibon Alkorta、José Elguero

  DOI：10.1016/j.ica.2009.12.059

  日期：2010.4

  The behavior in solution and in the solid state of 3(5)-phenyl-1H-pyrazole (7), 3(5)-phenyl-4-chloro-1H-pyrazole (6), 3(5)-phenyl-4-bromo-1H-pyrazole (1), and 3(5)-p-chlorophenyl-4-bromo-1H-pyrazole (8) is discussed in relation to their 3-phenyl (a)/5-phenyl (b) annular tautomerism. Two new X-ray structures are reported: a new polymorph of 1 and the structure of 6. The new polymorph is a 3-phenyl-1H-pyrazole 1a' trimer while the new structure is a 5-phenyl-1H-pyrazole 6b trimer. The combined use of NMR at low temperature and DFT calculations allows to discuss the tautomerism of the first three pyrazoles and to predict that the fourth one should be a tetramer formed by both tautomers, 8a and 8b. (C) 2010 Elsevier B. V. All rights reserved.