1-phenyl-5-(p-tolyl)-1H-pyrazole | 91869-68-0

• 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-phenyl-5-(p-tolyl)-1H-pyrazole
• 英文别名: 1-phenyl-5-p-tolylpyrazole；1-phenyl-5-p-tolyl-1H-pyrazole；1-Phenyl-5-p-tolyl-1H-pyrazol；5-(4-Methylphenyl)-1-phenylpyrazole
• CAS: 91869-68-0
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: WSWFQWDFHHVPTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1-phenyl-5-(p-tolyl)-1H-pyrazole
  参考文献：
  名称：

  v. Auwers; Mauss, Journal fur praktische Chemie (Leipzig 1954), 1927, vol. <2> 117, p. 331

  摘要：

  DOI：

文献信息

• Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles
  作者：J C JEYAVEERAN、CHANDRASEKAR PRAVEEN、Y ARUN、A A M PRINCE、P T PERUMAL

  DOI：10.1007/s12039-015-0993-9

  日期：2016.1

  The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, β-acetylenic oximes and α, β-acetylenic hydrazones is the centrepiece of the strategy. A range of acetylenic precursors were investigated to afford 28 examples of the products with good to excellent chemical yields. Selected compounds were screened for their cytotoxic potential towards COLO320 cancer cell lines. The IC50 values of the tested compounds were in the micromolar range, with the best compound, 5-(6-Methoxy-naphthalen-2-yl)-3-phenyl-isoxazole (3h) displaying an IC50 of 38.9 μM. For this compound, the crystal structure in complex with Aurora-A kinase was obtained which revealed details of its binding mode within the active site with a free energy of binding -9.54 kcal/mol.

  通过一种通用的环异构化方法，已经报道了取代异恶唑和吡唑的合成。金(III)氯化物促进α,β-炔基肟和α,β-炔基脒的环异构化的能力是该策略的核心。研究了一系列炔基前体，以良好的至优秀的化学收率得到了28个产物实例。选定的化合物对COLO320癌细胞系的细胞毒性潜力进行了筛选。测试化合物的IC50值在微摩尔范围内，其中最佳化合物5-(6-甲氧基萘-2-基)-3-苯基异恶唑(3h)的IC50值为38.9 μM。对于该化合物，获得了与Aurora-A激酶复合的晶体结构，揭示了其在活性位点内的结合模式，结合自由能为-9.54 kcal/mol。
• Novel crown ether functionalized imidazolium-based acidic ionic liquid catalyzed synthesis of pyrazole derivatives under solvent-free conditions
  作者：Dayanand Patil、Dattatraya Chandam、Abhijeet Mulik、Suryabala Jagdale、Prasad Patil、Madhukar Deshmukh

  DOI：10.1007/s11164-014-1782-7

  日期：2015.9

  [crown ether MIm] [HSO4] has been efficiently implemented for the synthesis of pyrazole derivatives using various substituted enaminones, hydrazine hydrate and phenyl hydrazine under solvent-free conditions. Structural novelty and task efficiency of the catalyst, high yields of desired products, greener approach attributing high atom economy and solvent-free conditions render this protocol suitable to

  摘要有效 设计了一种新颖设计的新型冠醚官能化咪唑基可重复使用的酸性离子液体[冠醚MIm] [HSO 4 ]，该方法可在无溶剂条件下使用各种取代的烯胺酮，水合肼和苯基肼合成吡唑衍生物。催化剂的结构新颖性和工作效率，所需产物的高收率，归因于高原子经济性和无溶剂条件的更绿色方法使该方案适合于应对当代有机化学的当前需求。在该方案中首次证明了使用冠醚官能化的离子液体作为催化剂的发明思想。 图形概要
• Ultrasound Assisted Synthesis of 1,5-Disubstituted Pyrazole using Cu(I) Catalyst
  作者：Ashok S. Pise、Arvind S. Burungale、Santosh S. Devkate

  DOI：10.14233/ajchem.2020.22432

  日期：2020.2.10

  A new efficient and convenient approach towards the synthesis of pyrazole is described. The α,β-unsaturated cyanoesters were obtained from substituted benzaldehyde and ethyl cyanoacetate by reported methods. 1,5-Disubstituted pyrazoles were synthesized from α,β-unsaturated cyanoester and phenyl hydrazine using sodium ethoxide as a base in the presence of 10 mol % Cu(I) catalyst in high yields within

  描述了一种新的有效且方便的合成吡唑的方法。采用已报道的方法由取代苯甲醛和氰基乙酸乙酯合成α,β-不饱和氰基酯。以乙醇钠为碱，在 10 mol% Cu(I) 催化剂存在下，在 60 ℃ 超声波照射下，75-90 分钟内以高产率合成 1,5-二取代吡唑，由 α,β-不饱和氰酯和苯肼合成。与传统方法相比，在超声波照射下反应速率大大提高，并且产率有所提高。
• BENZISOXAZOLES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150259334A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of general formula wherein Ar 1 /Ar 2 are phenyl or a 5 or 6-membered heteroaryl; R 1 /R 2 is hydrogen, halogen, lower alkyl, CF 3 or lower alkoxy; n,m are 1 or 2; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof, with the exception of the compound 2,1-benzisoxazole, 3-(4-chlorophenyl)-5-(1-phenyl-1H-pyrazol-5 -yl)-. The compounds may be used for the treatment of schizophrenia, obsessive-compulsive personality disorder, major depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction, Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of neuro-active drugs, such as alcohol, opiates, methamphetamine, phencyclidine and cocaine.

  本发明涉及一般式为的化合物 其中Ar1/Ar2是苯基或5或6成员杂环基；R1/R2是氢、卤素、低碳基、CF3或低烷氧基；n，m为1或2；或其药学上可接受的酸盐、外消旋体混合物或其相应的对映异构体，但不包括化合物2,1-苯并异噁唑，3-(4-氯苯基)-5-(1-苯基-1H-吡唑-5-基)-。这些化合物可用于治疗精神分裂症、强迫性人格障碍、重度抑郁症、双相情感障碍、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、惊恐障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗引起的认知功能障碍、唐氏综合症、自闭症谱系障碍、听力损失、耳鸣、脊髓小脑性共济失调、肌萎缩性侧索硬化症、多发性硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用，如酒精、鸦片类、甲基苯丙胺、邻-二氯苯基环已酮和可卡因。
• Hickson, Clare L.; McNab, Hamish, Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1569 - 1572
  作者：Hickson, Clare L.、McNab, Hamish

  DOI：——

  日期：——