2-(2-羟乙基)-5-甲基-4H-吡唑-3-酮 | 56226-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-(2-羟乙基)-5-甲基-4H-吡唑-3-酮
• 英文名称: 2-(2-hydroxyethyl)-5-methyl-2,4-dihydropyrazol-3-one
• 英文别名: 1-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5(4H)-one；1-(2-hydroxyethyl)-3-methyl-5-pyrazolone；1-(2-hydroxyethyl)-3-methyl-4H-pyrazolin-5-one；1-(2-Hydroxyethyl)-3-methyl-2-pyrazolin-5-one；2-(2-hydroxyethyl)-5-methyl-4H-pyrazol-3-one
• CAS: 56226-25-6
• 化学式: C₆H₁₀N₂O₂
• mdl: MFCD10485965
• 分子量: 142.158
• InChiKey: NKEKJMZYHSVIAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  255.1±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H315,H318,H335

反应信息

• 作为反应物：
  描述：

  2-(2-羟乙基)-5-甲基-4H-吡唑-3-酮 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 1-(2-hydroxyethyl)-4-hydroximino-3-methylpyrazolin-5-one
  参考文献：
  名称：

  Pesticidal substituted 4-heterocyclyloximino-pyrazolin-5-ones,

  摘要：

  公式为##STR1##的杀真菌取代的4-杂环氧亚氧基吡唑啉-5-酮，其中R.sup.1和R.sup.2分别独立地代表氢、烷基、烯基、炔基、氰基烷基、羟基烷基、烷氧基烷基、烷硫基烷基、烷氧羰基、羟基羰基烷基、烷氧羰基烷基、氨基羰基烷基、烷基氨基羰基烷基或二烷基氨基羰基烷基，或者分别代表未取代或取代的环氧丙基、芳基、杂环烷基或芳基，Het代表未取代或取代的杂环。

  公开号：

  US04988718A1
• 作为产物：
  描述：

  乙酰乙酸乙酯 以83%的产率得到
  参考文献：
  名称：

  SATO Y.; SHIMOJI Y.; ENDO K.; NISHINO H.; KOIKE H.; KUMAKURA S., YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR., 1978, 98, NO 3, 33+

  摘要：

  DOI：

文献信息

• p-Toluenesulphonic acid-promoted, I₂-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides
  作者：Xia Zhao、Lipeng Zhang、Tianjiao Li、Guiyan Liu、Haomeng Wang、Kui Lu

  DOI：10.1039/c4cc05237d

  日期：——

  Aryl pyrazolone thioethers were synthesized via the I2-catalysed cross-coupling of pyrazolones with aryl sulphonyl hydrazides in the presence of p-toluenesulphonic acid, which has been proposed to promote the reaction by facilitating the decomposition of sulphonyl hydrazides.

  芳基吡唑酮硫醚通过I2催化的吡唑酮与芳基磺酰肼在邻甲苯磺酸存在下的交叉耦合反应合成，该工艺已提议通过促进磺酰肼的分解来促进反应。
• Simple zwitterionic merocyanines as potential NLO chromophores
  作者：A. J. Kay、A. D. Woolhouse、G. J. Gainsford、T. G. Haskell、C. P. Wyss、S. M. Giffin、I. T. McKinnie、T. H. Barnes

  DOI：10.1039/b103148c

  日期：——

  A suite of zwitterionic pyridylidene-based merocyanines that contain no interconnecting π-bridge between the donor and acceptor rings has been synthesised and their second-order NLO properties evaluated largely by semi-empirical computational methods (MOPAC 97/AM1). Contrary to expectation, increasing the degree of inter-ring twist (θ), at least up to 55°, in these new pyridylideneazolone chromophores is found to have little or no effect on the figure of merit [μβ(0)]. An X-ray crystallographic appraisal of one of these chromophores, 14, reveals however that the twist angle (albeit in the solid state) is greater than that predicted by computation and that all other features are consistent with the highly zwitterionic nature of these systems. In spite of this, a combination of factors—insufficient acceptor strength, insufficient extent of conjugation and perhaps insufficient twist angle, in particular—clearly leads to the low values of the quadratic hyperpolarisabilities. The trade-off between targeting a more modest β from a minimum of π-conjugating framework between D and A (and therefore synthetic expediency) and seeking a moderate-to-high dipole moment has therefore resulted in only low figures of merit for these systems.Calculations performed on a suite of readily accessible, isoelectronic cyanines, in which the acceptor is a stabilised cyclopentadienide carbocycle rather than a heterocycle, have revealed the potential that these systems, exemplified by 27, have as NLO chromophores. Representative polymer-tetherable derivatives of this system have been prepared as have the corresponding TDI-based polyurethanes.

  合成了一系列不含捐赠体与受体环之间相互连接π桥的氨基吡啶基美罗青（merocyanine），并主要通过半经验计算方法（MOPAC 97/AM1）评估了它们的二阶非线性光学（NLO）特性。与预期相反，在这些新的氨基吡啶基氮酮色素中，增加环间扭转角度（θ），至少到55°，对性能指标[μβ(0)]几乎没有影响。然而，对其中一种色素14进行的X射线晶体学评估显示，虽然在固态中，扭转角度超过了计算预测的值，并且所有其他特征与这些系统的高度双性离子特性一致。尽管如此，一系列因素——如受体强度不足、共轭程度不足以及可能的扭转角度不足——显然导致了二次超极化率的低值。因此，在以D和A之间的最小π共轭框架为目标来获得更适度的β（因此在合成上的便利性）和寻求适度至高偶极矩之间进行了权衡，结果导致了这些系统的性能指标仅为低值。对一组易于获得的等电子氰类色素进行的计算显示，以稳定的环戊二烯基碳环作为受体，而非杂环的这些系统（以27为例）作为NLO色素具有潜力。已经制备了该系统的代表性聚合物连接衍生物，以及相应的基于TDI的聚氨酯。
• Synthesis, crystal structures and tautomerism in novel oximes based on hydroxyalkylpyrazolones
  作者：Julio Belmar、José Quezada、Claudio A. Jiménez、Pau Díaz-Gallifa、Jorge Pasán、Catalina Ruiz-Pérez

  DOI：10.1039/c3nj00163f

  日期：——

  Two novel hydroxyethyl pyrazolones were obtained by condensation of 2-hydroxyethylhydrazine with ethyl acetoacetate or ethyl benzoylacetate, later nitrosation of the C4 carbon atom in the heterocyclic moiety, afforded two novel oxime-derivatives. The 1H and 13C NMR data show that 1-(2-hydroxyethyl)-3-methyl-5-pyrazolone (1) is largely present together with a very small amount of the 5-one tautomer

  通过缩合得到两个新的羟乙基吡唑啉酮。 2-羟乙基肼 和 乙酰乙酸乙酯 或者 苯甲酰乙酸乙酯后来，杂环部分中的C4碳原子进行亚硝化，得到了两种新颖的肟衍生物。的1 H和13个C NMR数据显示1-（2-羟乙基）-3-甲基-5-吡唑啉酮（1）与少量的5一互变异构体一起存在DMSO- d 6; 相比之下，1-（2-羟乙基）-3-苯基-5-吡唑啉酮（2）被发现为一个互变异构体CDCl 3。出现两个非对映异构体DMSO- d 6 在 1-（2-羟乙基）-3-甲基-4-羟基亚氨基-5-吡唑啉酮（3）在1-（2-羟乙基）-3-苯基-4-羟基亚氨基-5-吡唑啉酮（4）中存在一个物种CDCl 3。尽管所用溶剂的极性存在差异，但在两种情况下，肟互变异构体均被证明更稳定。DMSO- d 6仅允许E / Z非对映异构体之间达到平衡。的单晶X射线衍射数据1，3和4给出，它们表明1发生是由于酮-烯胺互变异构体，在与溶液中的情况形成鲜明对比;
• 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。