3-isopropoxy-5-methyl-1H-pyrazole | 1116655-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isopropoxy-5-methyl-1H-pyrazole
• 英文别名: 3-isopropyloxy-1-methylpyrazole；3-Isopropoxy-5-methylpyrazole；5-methyl-3-propan-2-yloxy-1H-pyrazole
• CAS: 1116655-93-6
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: RAXMRWMKBAHEJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-isopropoxy-5-methyl-1H-pyrazole 在 碘 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以82%的产率得到4-iodo-3-isopropoxy-5-methyl-1H-pyrazole
  参考文献：
  名称：

  Alkoxypyrazoles and the process for their preparation

  摘要：

  本发明涉及一种烷氧基吡唑的制备方法，以及新的烷氧基吡唑化合物。

  公开号：

  EP2151433A1
• 作为产物：
  描述：

  乙酰乙酸异丙酯 在 盐酸肼 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以55%的产率得到3-isopropoxy-5-methyl-1H-pyrazole
  参考文献：
  名称：

  An Improved Preparation of 3-Alkoxypyrazoles

  摘要：

  烷基乙酰乙酸酯与肼之间的缩合反应构成了著名的Knorr合成方法，生成吡唑-3/5-酮。然而，近期报告描述了一种替代反应路径，使用肼盐得到的3/5-烷氧基吡唑产量较低。目前尚未报告用于选择性合成3-烷氧基吡唑的一般方法，因此我们集中研究这一副反应，试图将其转化为主要转化反应。根据起始材料的不同，获得了多种3-烷氧基吡唑（甲氧基、乙氧基、苄氧基、异丙氧基、烯丙氧基），产率高达56%。

  DOI：

  10.1055/s-0028-1083186

文献信息

• Alkoxypyrazoles and the process for their preparation
  申请人：Institut Pasteur

  公开号：EP2151433A1

  公开（公告）日：2010-02-10

  The present invention relates to a alkoxypyrazoles preparation process, and new alkoxypyrazole compounds.

  本发明涉及一种烷氧基吡唑的制备方法，以及新的烷氧基吡唑化合物。
• N-arylation of 3-alkoxypyrazoles, the case of the pyridines
  作者：Sandrine Guillou、Frédéric J. Bonhomme、Di Betina Chahine、Olivier Nesme、Yves L. Janin

  DOI：10.1016/j.tet.2010.02.032

  日期：2010.4

  In the course of a research program focused on the preparation of libraries of new chemical entities derived from 3-alkoxypyrazoles, we studied their N-pyridylation using 2, 3 or 4-bromopyridines This was achieved using Cristau and Taillefer copper-catalyzed arylation method and mostly led to the 3-alkoxy-1H-pyrazol-1-yl pyridine isomer along with lesser amount of the alternative 5-alkoxy-1H-pyrazol-1-yl pyridine The structures of these isomers were often established via their chemical tansformations and sometimes recourse to unambiguous synthetic routes for comparison purposes The alternative use of 2-fluoropyridine-based arylation was also investigated and lifted some of the limitations encountered in the course of this study (C) 2010 Elsevier Ltd All rights reserved
• [EN] NEW ALKOXYPYRAZOLES<br/>[FR] NOUVEAUX ALCOXYPYRAZOLES
  申请人：PASTEUR INSTITUT

  公开号：WO2010015657A2

  公开（公告）日：2010-02-11

  The present invention relates to a alkoxypyrazoles preparation process, and new alkoxypyrazoles compounds.
• An Improved Preparation of 3-Alkoxypyrazoles
  作者：Yves Janin、Sandrine Guillou、Frédéric Bonhomme

  DOI：10.1055/s-0028-1083186

  日期：——

  The condensation between alkyl acetoacetates and hydrazines constitutes the very well-known Knorr synthetic method leading to pyrazol-3/5-ones. However, contemporary reports describe an alternate reaction pathway leading to low yields of 3/5-alkoxypyrazoles using hydrazine salts. No general method for the selective synthesis of 3-alkoxypyrazoles has been reported to date, hence we focused on this side reaction in an attempt to turn it into the main transformation. Depending on the starting material, various 3-alkoxypyrazoles (methoxy, ethoxy, benzyloxy, isopropoxy, allyloxy) were obtained in up to 56% yield.

  烷基乙酰乙酸酯与肼之间的缩合反应构成了著名的Knorr合成方法，生成吡唑-3/5-酮。然而，近期报告描述了一种替代反应路径，使用肼盐得到的3/5-烷氧基吡唑产量较低。目前尚未报告用于选择性合成3-烷氧基吡唑的一般方法，因此我们集中研究这一副反应，试图将其转化为主要转化反应。根据起始材料的不同，获得了多种3-烷氧基吡唑（甲氧基、乙氧基、苄氧基、异丙氧基、烯丙氧基），产率高达56%。
• Nitrogen's reactivity of various 3-alkoxypyrazoles
  作者：Sandrine Guillou、Frédéric J. Bonhomme、Yves L. Janin

  DOI：10.1016/j.tet.2009.01.099

  日期：2009.3

  Our current interest in the design of original chemical libraries featuring a pyrazole nucleus led us to focus on the chemistry of the 3-alkoxy-5-methylpyrazoles we have recently made readily available. With in mind the preparation of an array of the less accessible 1-arylpyrazol-3-ones, the present report describes the respective nitrogen's reactivity of various 3-alkoxypyrazoles toward arylation reaction, using arylboronic acids, as well as alkylation reactions using methyl iodide or benzylbromide. The structure assignments of the isomers obtained were achieved using long distance N-15-H-1 NMR correlation measurements or by the recourse to unambiguous synthetic pathways. (c) 2009 Elsevier Ltd. All rights reserved.