4-iodo-3-isopropoxy-5-methyl-1H-pyrazole | 1147770-75-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-iodo-3-isopropoxy-5-methyl-1H-pyrazole
• 英文别名: 4-Iodo-3-isopropoxy-5-methylpyrazole；4-iodo-5-methyl-3-propan-2-yloxy-1H-pyrazole
• CAS: 1147770-75-9
• 化学式: C₇H₁₁IN₂O
• 分子量: 266.082
• InChiKey: VNKRERFIICRRIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 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：

  2-溴吡啶 、 4-iodo-3-isopropoxy-5-methyl-1H-pyrazole 在 copper(I) oxide 、 N,N'-bis(2-pyridylmethylidene)-1,2-(RS,RS)-cyclohexanediamine 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以45%的产率得到2-(3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyridine
  参考文献：
  名称：

  N-arylation of 3-alkoxypyrazoles, the case of the pyridines

  摘要：

  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

  DOI：

  10.1016/j.tet.2010.02.032
• 作为产物：
  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

文献信息

• 4-Arylation of 3-alkoxypyrazoles
  作者：Sandrine Guillou、Olivier Nesmes、Mikhail S. Ermolenko、Yves L. Janin

  DOI：10.1016/j.tet.2009.01.109

  日期：2009.4

  Following the study of the alkoxypyrazoles nitrogen's reactivity toward arylation or alkylation reactions, we report here our results on the introduction of various aryl groups on carbon 4 position of 3-alkoxypyrazoles. This was achieved from the corresponding 4-halogeno derivatives via a Suzuki–Miyaura aryl–aryl coupling reaction. The unexpected difficulties (lack of reactivity or unwanted halogen

  在研究了烷氧基吡唑氮对芳基化或烷基化反应的反应性之后，我们在这里报告了在3-烷氧基吡唑的碳4位上引入各种芳基的结果。这是通过Suzuki-Miyaura芳基-芳基偶联反应从相应的4-卤代衍生物获得的。不含NH的4-卤代吡唑的C-4芳基化过程中遇到的出乎意料的困难（缺乏反应性或不希望的卤素还原）导致我们设计了该重复性问题的解决方案。还使用在乙酸中的溴化氢或在二氯甲烷中的三溴化硼研究了3-烷氧基的裂解。在一种情况下，这导致观察到显着的邻近基团辅助的亲电芳基硼酸酯化。
• 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.
• [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.