1-(hydroxymethyl)-5-methyl 1H-pyrazole-3-carboxylate

• 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-(hydroxymethyl)-5-methyl 1H-pyrazole-3-carboxylate
• 英文别名: N-hydroxymethyl-[3-carbomethoxy-5-methyl]pyrazole；1-(hydroxymethyl)-3-methoxycarbonyl-5-methyl-pyrazole；methyl 1-(hydroxymethyl)-5-methyl-1H-pyrazole-3-carboxylate；methyl 1-(hydroxymethyl)-5-methylpyrazole-3-carboxylate
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: RLSHNRKCBZFRJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(hydroxymethyl)-5-methyl 1H-pyrazole-3-carboxylate 在 乙酸铵 作用下， 以 乙腈 为溶剂， 以53%的产率得到Methyl 1-[[bis[(3-methoxycarbonyl-5-methylpyrazol-1-yl)methyl]amino]methyl]-5-methylpyrazole-3-carboxylate
  参考文献：
  名称：

  的合成Ñ，Ñ ' -双和Ñ，Ñ，Ñ '，Ñ ' -四- [（3,5-二-取代的- 1-吡唑基）甲基]对苯二胺类：新的候选配体的金属配合物的电线

  摘要：

  一系列三齿配体的Ñ，ñ -双- [（二取代-1-吡唑基）甲基]芳基胺2 -图3a，b和苄图4a，b，四齿Ñ，Ñ ' -双- [（二取代-1- -（吡唑基）甲基]对苯二胺7a，b和六齿的N，N，N '，N'-四-[（二取代-1-吡唑基）甲基]对苯二胺8a，b通过芳基胺，苄基胺或对苯二胺与N-羟甲基二取代的吡唑1a，b的缩合，可以高收率制备α-己内酰胺。描述了这些各种多齿配体的合成和表征。

  DOI：

  10.1016/j.tet.2006.01.034
• 作为产物：
  描述：

  聚合甲醛 、 5-甲基吡唑-3-甲酸甲酯 以 乙醇 为溶剂， 生成 1-(hydroxymethyl)-5-methyl 1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  Tridentate bipyrazole compounds with a side-arm as a new class of antitumor agents

  摘要：

  通过一步法合成且产率良好的八个具有不同侧臂的三齿双吡唑衍生物。利用MTT比色法测定产物对三类肿瘤细胞系的细胞毒活性——人乳腺癌细胞系MDA-MB-231、人前列腺癌细胞系PC3和人结直肠癌细胞系LoVo。结构-活性关系反映了取代药物的影响。在该系列中，有两种化合物对LoVo细胞系显示出显著的体外抗增殖活性，IC50值分别为2.6至2.7 μg ml−1。根据Lipinski规则，所有化合物都具有适合药物的特征。

  DOI：

  10.1007/s11164-012-0993-z

文献信息

• Solid-state detection of gases by use of thin films based on pyrazole units, and morphological characterization of the films by AFM
  作者：R. Touzani、S. El Kadiri、A. Zerrouki、G. Vasapollo、S. Scorrano、R. Del Sole、M. G. Manera、R. Rella

  DOI：10.1007/s11164-012-0541-x

  日期：2012.11

  Synthesis of a series of heterocyclic compounds based on pyrazole units is reported. The possibility of using these compounds, as solid-state thin layers deposited on quartz substrates, for optical recognition of hazardous pollutant gases was investigated. The gases SO2, NO2, CO, CH4, and NH3 were studied. Two of the ligand layers had reversible sensitivity toward SO2, with good reaction time. The presence of CO, CH4 NO2, and NH3 had no effect on the optical properties. Morphological characterization by use of AFM microscopy was also investigated.

  报道了基于吡唑单元的系列杂环化合物的合成。研究了这些化合物作为沉积在石英基板上的固态薄层，用于危险污染物气体的光学识别的可能性。研究了SO2、NO2、CO、CH4和NH3气体。其中两种配体层对SO2具有可逆敏感性，反应时间良好。CO、CH4、NO2和NH3的存在对光学性质没有影响。还通过AFM显微镜进行了形态学表征研究。
• EFFICIENT SYNTHESIS OF NEW NITROGEN DONOR CONTAINING TRIPODS UNDER MICROWAVE IRRADIATION AND WITHOUT SOLVENT
  作者：Rachid Touzani、Abdelkrim Ramdani、Taibi Ben-Hadda、Sghir El Kadiri、Olivier Maury、Hubert Le Bozec、Pierre H. Dixneuf

  DOI：10.1081/scc-100104040

  日期：2001.1

  Five new N,N-bis(pyrazole-1-yl-methyl) alkylamines have been prepared in one step by condensation of two equivalents of 1-(hydroxymethyl)-3,5-disubstituted pyrazoles with a series of primary amines. This reaction is carried out under microwave irradiation (60 W) in the absence of solvent for 20 m and affords high yields (75–90%) of mixed nitrogen donor tripodal molecules.

  通过将两当量的 1-(羟甲基)-3,5-二取代吡唑与一系列伯胺缩合，一步制备了五种新的 N,N-双(吡唑-1-基-甲基)烷基胺。该反应在微波辐射 (60 W) 下在没​​有溶剂的情况下进行 20 m，并提供高产率 (75-90%) 的混合氮供体三足分子。
• Crystal Structure of N,N-bis-(3-Carbomethoxy-5-methyl-pyrazol-1-ylmethyl)aniline
  作者：Maria Daoudi、Najib Larbi、Driss Benjelloun、Abdelali Kerbal、Jean Launay、Jacques Bonvoisin、Joël Jaud、Mostafa Mimouni、Taibi Ben-Hadda

  DOI：10.3390/70900690

  日期：——

  The tripodal ligand N,N-bis-(3-carbomethoxy-5-methylpyrazol-1-yl)methyl aniline (2) has been prepared by the condensation of aniline with two equivalents of N-hydroxymethyl[3-carbomethoxy-5-methyl]pyrazole. The molecule consists of two structurally analogous 3-carbomethoxy-5-methylpyrazol-1-ylmethyl moieties, which adopt a transoidal conformation via a central aniline ring, suggesting that this tripodal ligand is highly flexible and could accommodate many metals by coordination.

  三元配体 N,N-双-(3-甲氧基-5-甲基吡唑-1-基)甲基苯胺 (2) 是由苯胺与两个等量的 N-羟甲基[3-甲氧基-5-甲基]吡唑缩合而成。该分子由两个结构类似的 3-甲氧羰基-5-甲基吡唑-1-基甲基组成，它们通过一个中央苯胺环形成一个横向构象，这表明这种三足配体具有很高的灵活性，可以通过配位容纳多种金属。
• Synthesis of N,N′-bis and N,N,N′,N′-tetra-[(3,5-di-substituted-1-pyrazolyl)methyl]para-phenylenediamines: new candidate ligands for metal complex wires
  作者：Maria Daoudi、Najib Ben Larbi、Abdelali Kerbal、Brahim Bennani、Jean-Pierre Launay、Jacques Bonvoisin、Taibi Ben Hadda、Pierre H. Dixneuf

  DOI：10.1016/j.tet.2006.01.034

  日期：2006.3

  A series of tridentate ligands N,N-bis-[(di-substituted-1-pyrazolyl)methyl]arylamines 2–3a,b and benzylamine 4a,b, tetradentate N,N′-bis-[(di-substituted-1-pyrazolyl)methyl]para-phenylenediamines 7a,b and hexadentate N,N,N′,N′-tetra-[(di-substituted-1-pyrazolyl)methyl]para-phenylenediamines 8a,b has been prepared in good yield by condensation of arylamines, benzylamine or para-phenylenediamine with

  一系列三齿配体的Ñ，ñ -双- [（二取代-1-吡唑基）甲基]芳基胺2 -图3a，b和苄图4a，b，四齿Ñ，Ñ ' -双- [（二取代-1- -（吡唑基）甲基]对苯二胺7a，b和六齿的N，N，N '，N'-四-[（二取代-1-吡唑基）甲基]对苯二胺8a，b通过芳基胺，苄基胺或对苯二胺与N-羟甲基二取代的吡唑1a，b的缩合，可以高收率制备α-己内酰胺。描述了这些各种多齿配体的合成和表征。
• Tridentate bipyrazole compounds with a side-arm as a new class of antitumor agents
  作者：Fouad Malek、Nihed Draoui、Olivier Feron、Smaail Radi

  DOI：10.1007/s11164-012-0993-z

  日期：2014.2

  Eight tridentate bipyrazole derivatives with different side arms have been prepared in one step and with good yields. The products were screened for their cytotoxic activity against three tumor cell lines—human breast cancer cell line MDA-MB231, human prostate cancer cell line PC3, and human colorectal cell line LoVo, by use of colorimetric MTT assay. Structure–activity relationships reflected the effect of substituted drugs. Among this series, two compounds had remarkable in-vitro antiproliferative activity against the LoVo cell line with IC50 values ranging from 2.6 to 2.7 μg ml−1. All the compounds had suitable drug-like characteristics according to Lipinski’s rule.

  通过一步法合成且产率良好的八个具有不同侧臂的三齿双吡唑衍生物。利用MTT比色法测定产物对三类肿瘤细胞系的细胞毒活性——人乳腺癌细胞系MDA-MB-231、人前列腺癌细胞系PC3和人结直肠癌细胞系LoVo。结构-活性关系反映了取代药物的影响。在该系列中，有两种化合物对LoVo细胞系显示出显著的体外抗增殖活性，IC50值分别为2.6至2.7 μg ml−1。根据Lipinski规则，所有化合物都具有适合药物的特征。