methyl β-(3,5-dimethyl-1H-pyrazol-1-yl)propionate | 4819-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl β-(3,5-dimethyl-1H-pyrazol-1-yl)propionate
• 英文别名: methyl 3-(3,5-dimethyl-1H-pyrazol-1-yl)propionate；3-(3,5-dimethyl-pyrazol-1-yl)-propionic acid methyl ester；Methyl 3-(3,5-Dimethyl-1H-pyrazol-1-yl)propanoate；methyl 3-(3,5-dimethylpyrazol-1-yl)propanoate
• CAS: 4819-19-6
• 化学式: C₉H₁₄N₂O₂
• mdl: MFCD08701077
• 分子量: 182.222
• InChiKey: QFALMQGMKGACLP-UHFFFAOYSA-N

物化性质

• 沸点：
  124-125 °C(Press: 7 Torr)
• 密度：
  1.069 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl β-(3,5-dimethyl-1H-pyrazol-1-yl)propionate 在 sodium hydroxide 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 4.0h， 生成 β-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionic acid
  参考文献：
  名称：

  Vilsmeier-Haak formylation of 3,5-dimethylpyrazoles

  摘要：

  Formylation of N-alkyl-3,5-dimethyl-1H-pyrazoles according to Vilsmeier-Haak led to the formation of the corresponding 4-formyl derivatives. 3,5-Dimethyl-1H-pyrazole having no substituent on the nitrogen atom failed to undergo formylation at the 4 position under analogous conditions. 3,5-Dimethyl-1H-pyrazole-4-carbaldehyde was synthesized by alkaline hydrolysis of methyl [3-(4-formyl-3,5-dimethyl-1H-pyrazol-1-yl)propionate and subsequent heating of the acid thus formed.

  DOI：

  10.1134/s1070363206110260
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 丙烯酸甲酯（MA） 以 neat (no solvent) 为溶剂， 以99 %的产率得到methyl β-(3,5-dimethyl-1H-pyrazol-1-yl)propionate
  参考文献：
  名称：

  氯化钯(II) 吡唑基丙酸酯配合物

  摘要：

  研究了新配体3-(吡唑-1-基)甲基丙酸酯(L1)和3-(2,4-二甲基吡唑-1-基)甲基丙酸酯(L2)的合成及其与钯(II)的络合。在我们看来，L1最好通过Cs 2 CO 3催化的迈克尔加成和L2通过无催化剂和无溶剂的反应来制备。L1和L2均与PdCl 2 (COD)反应，分别产生反式PdCl 2 (L1) 2 ( 3 )和反式PdCl 2 (L2) 2 ( 4 )。两种新配合物的晶体结构均已确定。当配合物4时观察到异构化溶解于CDCl 3或CD 3 CN。动力学数据表明这是两个方向上的一阶平衡。我们认为这可能是由于反式异构体异构化为顺式异构体。新配体 L1 和 L2 易于制备且产量近乎定量，因此可能对进一步研究有用。

  DOI：

  10.1002/zaac.202300076

文献信息

• Compounds which inhibit beta-secretase activity and methods of use thereof
  申请人：Oklahoma Medical Research Foundation

  公开号：US20040121947A1

  公开（公告）日：2004-06-24

  Compounds inhibit memapsin 2 &bgr;-secretase activity and selectively inhibit memapsin 2 &bgr;-secretase activity relative to memapsin 1 &bgr;-secretase activity. The compounds are employed in methods to inhibit memapsin 2 &bgr;-secretase activity, in the treatment of Alzheimer's disease, in the inhibition of hydrolysis of a &bgr;-secretase site of a &bgr;amyloid precursor protein and to decrease &bgr;-amyloid protein in in vitro samples and in mammals. Proteins of memapsin 2 associated with compounds of the invention are crystallized.

  这些化合物抑制memapsin 2 β-分泌酶活性，并相对选择性地抑制memapsin 2 β-分泌酶活性，而相对于memapsin 1 β-分泌酶活性。这些化合物用于抑制memapsin 2 β-分泌酶活性的方法，用于治疗阿尔茨海默病，用于抑制β淀粉样前体蛋白的β-分泌酶位点的水解，并用于减少体外样本和哺乳动物中的β-淀粉样蛋白。与本发明的化合物相关的memapsin 2蛋白被结晶。
• Synthesis of N- and C-azolyl-substituted pyrazolo[1,5-a]pyrimidines by recyclization of pyrimidinium salts
  作者：Gevorg G. Danagulyan、Araksya K. Tumanyan、Oganes S. Attaryan、Rafael A. Tamazyan、Anna G. Danagulyan、Armen G. Ayvazyan

  DOI：10.1007/s10593-015-1724-3

  日期：2015.5

  We studied the reaction of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidinium iodide with hydrazides of N-azolyl- and D-pyrazolylsubstituted carboxylic acids, which were synthesized by reacting the respective esters with hydrazine hydrate. This reaction was shown to result in recyclization and formation of ethyl 2-(pyrazolylalkyl)- and 2-(azolylalkyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylates. Besides pyrazolopyrimidines, the separation of reaction mixture provided in some cases also another recyclization product, 2-hydroxy-5,7-dimethylpyrazolo[1,5-a]pyrimidine.
• Vilsmeier-Haack formylation of 1H-pyrazoles
  作者：K. S. Badalyan、A. E. Akopyan、H. S. Attaryan、G. V. Asratyan

  DOI：10.1134/s1070363214040331

  日期：2014.4
• COMPOUNDS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF
  申请人：GHOSH Arun K.

  公开号：US20100267609A1

  公开（公告）日：2010-10-21

  Compounds inhibit memapsin 2 β-secretase activity and selectively inhibit memapsin 2 β-secretase activity relative to memapsin 1 β-secretase activity. The compounds are employed in methods to inhibit memapsin 2 β-secretase activity, in the treatment of Alzheimer's disease, in the inhibition of hydrolysis of a β-secretase site of a β-amyloid precursor protein and to decrease β-amyloid protein in in vitro samples and in mammals. Proteins of memapsin 2 associated with compounds of the invention are crystallized.
• [EN] BETA-SECRETASE INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS DE LA BETA-SECRETASE ET LEURS PROCEDE D'UTILISATION
  申请人：OKLAHOMA MED RES FOUND

  公开号：WO2003039454A2

  公开（公告）日：2003-05-15

  Compounds inhibit memapsin 2 β-secretase activity and selectively inhibit memapsin 2 β-secretase activity relative to memapsin 1 β-secretase activity. The compounds are employed in methods to inhibit memapsin 2 β-secretase activity, in the treatment of Alzheimer's disease, in the inhibition of hydrolysis of a β-secretase site of a β-amyloid precursor protein and to decrease β-amyloid protein in in vitro samples and in mammals. Proteins of memapsin 2 associated with compounds of the invention are crystallized.