5-methyl-2-(2-methylphenyl)-2,4-dihydropyrazol-3-one | 29211-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methyl-2-(2-methylphenyl)-2,4-dihydropyrazol-3-one
• 英文别名: 3-methyl-1-(2-methylphenyl)-2-pyrazolin-5-one；5-methyl-2-(o-tolyl)-2,4-dihydropyrazol-3-one；3-methyl-1-(o-tolyl)-1H-pyrazol-5(4H)-one；5-methyl-2-o-tolyl-1,2-dihydro-pyrazol-3-one；3-Methyl-1--pyrazolon-(5)；3-methyl-1-(2-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one；5-methyl-2-(2-methylphenyl)-4H-pyrazol-3-one
• CAS: 29211-55-0
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00461405
• 分子量: 188.229
• InChiKey: GENSTRUCMIZOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(2-methylphenyl)-2,4-dihydropyrazol-3-one 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(3,3-dimethyl-1-(piperidin-1-yl)butan-2-yl)thiourea 、 sodium acetate 、 溶剂黄146 作用下， 反应 121.0h， 生成 3-methyl-4-((S)-2-nitro-1-phenylethyl)-1-o-tolyl-1H-pyrazol-5-yl benzoate
  参考文献：
  名称：

  α-硝基酮与不饱和吡唑啉酮的有机催化不对称迈克尔/半缩酮化/复古-羟醛反应：3-酰氧基吡唑的合成

  摘要：

  描述了不饱和吡唑啉酮和α-硝基酮之间的有机催化不对称级联迈克尔/半缩醛化/复古-醛醇反应。发现双官能硫脲催化剂对于该反应是有效的。使用10 mol％的催化剂，在温和的反应条件下，各种3-酰氧基吡唑的收率高，对映选择性也好。

  DOI：

  10.1021/acs.orglett.6b03823
• 作为产物：
  描述：

  2-氯甲苯 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 N-[2-二(1-金刚烷)磷苯基]吗啉 、 一水合肼 、 溶剂黄146 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 5-methyl-2-(2-methylphenyl)-2,4-dihydropyrazol-3-one
  参考文献：
  名称：

  Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid

  摘要：

  N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.022

文献信息

• Catalytic System‐Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones
  作者：Feifei Fang、Shulei Hu、Chunpu Li、Qian Wang、Run Wang、Xu Han、Yu Zhou、Hong Liu

  DOI：10.1002/anie.202105857

  日期：2021.9.20

  system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N−N bond activation/[n+1] annulation cascade, a C(sp2)-H

  本文报道了一种催化系统控制的发散反应策略，通过精确的化学键活化/[ n +1] 环化级联，从简单易得的起始材料构建四种有趣的螺杂环骨架。四氮杂螺杂环和三氮杂螺杂环支架可以通过选择性 NN 键激活/[ n +1] 环化级联、C(sp 2 )-H 激活/[4+1] 环化和新型串联 C(sp 2 )-H/C(sp 3)−H 键活化/[4+1] 环化策略，以及广泛的底物、中等至优异的产率和有价值的转化。更重要的是，在这些转化中，我们首次捕捉到了不同催化体系下吡唑烷酮的 NN键活化和 C(sp 3 )-H 键活化。
• Rhodium‐Catalyzed [4+2] Annulation of N‐Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone‐Fused Cinnolines
  作者：Chih‐Yu Lin、Wan‐Wen Huang、Ying‐Ti Huang、Sandip Dhole、Chung‐Ming Sun

  DOI：10.1002/ejoc.202101005

  日期：2021.9.21

  An efficient synthesis of novel dinitrogen-fused heterocycles, such as pyrazolo[1,2-a]cinnoline derivatives, has been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with diazo compounds. This reaction proceeds through a cascade C−H activation/intramolecular cyclization under mild reaction conditions and features a broad substrate scope.

  新型二氮稠合杂环的有效合成，例如吡唑并[1,2- a ]肉啉衍生物，已通过铑(III)催化的N-芳基吡唑-5-酮与重氮化合物的反应完成。该反应在温和的反应条件下通过级联 CH 活化/分子内环化进行，具有广泛的底物范围。
• <i>N</i>-Triflination of pyrazolones: a new method for N–S bond formation
  作者：Ahwan Panigrahi、Nachimuthu Muniraj、Kandikere Ramaiah Prabhu

  DOI：10.1039/d1ob00862e

  日期：——

  developed for the N-triflination of pyrazolones using CF3SO2Na (Langlois reagent) and phenyliodine(III)bis(trifluoroacetate) (PIFA). This reaction takes place at the imine nitrogen centre instead of the more reactive C4-position, forming a new N–S bond. A variety of pyrazolone derivatives were subjected to the reaction. Unlike the previous reports on sulfenylation or sulfonylation of pyrazolone, wherein

  使用CF 3 SO 2 Na（朗格鲁瓦试剂）和苯碘（III）双（三氟乙酸）（PIFA）开发了一种在5分钟内快速完成的简单方法，用于吡唑啉酮的N-三氟化。该反应发生在亚胺氮中心而不是更具反应性的 C4 位，形成新的 N-S 键。多种吡唑啉酮衍生物进行反应。与之前关于吡唑啉酮磺酰化或磺酰化的报道不同，其中形成了相应的 C-S 键，这种新方法导致在室温下形成杂-杂原子键（N-S 键）。
• PREVENTIVE AND/OR THERAPEUTIC DRUGS FOR INFLAMMATORY INTESTINAL DISEASES
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1553087A1

  公开（公告）日：2005-07-13

  The object of the present invention is to provide a medicament useful for preventing and/or treating inflammatory bowel disease. The present invention provides a medicament for preventing and/or treating inflammatory bowel disease which comprises as an active ingredient a pyrazolone derivative represented by the following formula (I) or a physiologically acceptable salt thereof, or a hydrate thereof or a solvate thereof: wherein R1 represents a hydrogen atom, an aryl group, an alkyl group, or an alkoxycarbonylalkyl group; R2 represents a hydrogen atom, an aryloxy group, an arylmercapto group, an alkyl group or a hydroxyalkyl group; or R1 and R2 are combined with each other to represent an alkylene group; and R3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, a hydroxyalkyl group, a benzyl group, a naphthyl group, a phenyl group, or a phenyl group substituted with 1 to 3 substituents selected from the group consisting of an alkyl group, an alkoxy group, a hydroxyalkyl group, an alkoxycarbonyl group, an alkylmercapto group, an alkylamino group, a dialkylamino group, a halogen atom, a trifluoromethyl group, a carboxyl group, a cyano group, a hydroxyl group, a nitro group, an amino group and an acetamide group.

  本发明的目的是提供一种用于预防和/或治疗炎性肠病的药物。本发明提供了一种药物，用于预防和/或治疗炎性肠病，其包括以下式（I）所表示的吡唑酮衍生物作为活性成分，或其生理上可接受的盐，或其水合物或溶剂化合物：其中R1表示氢原子，芳基，烷基或烷氧羰基烷基；R2表示氢原子，芳氧基，芳硫基，烷基或羟基烷基；或R1和R2结合在一起表示烷基；R3表示氢原子，烷基，环烷基，羟基烷基，苄基，萘基，苯基或苯基，其被1至3个取代基所取代，所述取代基被选自羟基烷基，烷氧基，羟基烷氧基，烷氧羰基，烷硫基，烷基氨基，二烷基氨基，卤素原子，三氟甲基基团，羧基，氰基，羟基，硝基，氨基和乙酰胺基。
• AGENT FOR PREVENTING AND/OR TREATING OPHTHALMOLOGIC DISEASES
  申请人：MITSUBISHI TANABE PHARMA CORPORATION

  公开号：US20170273949A1

  公开（公告）日：2017-09-28

  It is an object of the present invention to provide a novel medicament for preventing and/or treating ophthalmologic diseases caused by ocular angiogenesis. According to the present invention, provided is a medicament for preventing and/or treating ophthalmologic diseases caused by ocular angiogenesis, which comprises, as an active ingredient, a pyrazolone derivative such as 3-methyl-1-phenyl-2-pyrazolin-5-one, or a physiologically acceptable salt thereof, or a hydrate thereof or a solvate thereof.

  本发明的目的是提供一种新型药物，用于预防和/或治疗由眼部血管生成引起的眼科疾病。根据本发明，提供了一种用于预防和/或治疗由眼部血管生成引起的眼科疾病的药物，其包括作为活性成分的吡唑酮衍生物，如3-甲基-1-苯基-2-吡唑啉-5-酮，或其生理上可接受的盐，或其水合物或溶剂化物。