methyl 5-methyl-2-furyl ketoxime | 73750-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: methyl 5-methyl-2-furyl ketoxime
• 英文别名: 1-(5-methyl-[2]furyl)-ethanone oxime；1-(5-Methyl-[2]furyl)-aethanon-oxim；2-Acetyl-5-methylfuran oxime；(E)-N-[1-(5-Methylfuran-2-YL)ethylidene]hydroxylamine；N-[1-(5-methylfuran-2-yl)ethylidene]hydroxylamine
• CAS: 73750-15-9；78073-03-7；78073-04-8
• 化学式: C₇H₉NO₂
• mdl: MFCD05263153
• 分子量: 139.154
• InChiKey: HZNJITMIJAXIJG-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl-2-furyl ketoxime 在 盐酸 、 一水合肼 、 溶剂黄146 、 sodium hydroxide 、 锌 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 25.08h， 生成 1,6-dimethyl-2,4-dihydro-1H-pyrrolo[1,2-a]pyrazin-3-one
  参考文献：
  名称：

  呋喃环开口-吡咯环封闭。1,2,3,4-四氢吡咯并[1,2 - a ]吡嗪-3-酮的简单路线

  摘要：

  我们在这里报告了呋喃开环-Paal-Knorr吡咯合成序列在将糠胺转化为1,2,3,4-四氢吡咯并[1,2 - a ]吡嗪-3-酮中的应用。

  DOI：

  10.1016/j.tetlet.2013.05.066
• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 methyl 5-methyl-2-furyl ketoxime
  参考文献：
  名称：

  A new method for preparation of 3-hydroxypyridines from furfurylamines by photooxygenation.

  摘要：

  对糠胺衍生物进行低温光氧合（-70°C），然后用三苯基膦处理，可获得高产率的 3-羟基吡啶。

  DOI：

  10.1248/cpb.39.181

文献信息

• Untersuchungen über furan-verbindungen—V
  作者：G. Ocskay、L. Vargha

  DOI：10.1016/0040-4020(58)88031-x

  日期：1958.1

  Several pairs of syn and anti-furyl-ketoximes have been prepared, which have been characterised by their acetates, benzoates and p-toluenesulphonates. The configurations of the ketoximes were successfully established by chemical means and by their u.v. spectra

  已经制备了几对顺式和反式-呋喃酮酮肟，其特征在于它们的乙酸盐，苯甲酸盐和对甲苯磺酸盐。通过化学方法及其紫外光谱成功建立了酮肟的构型
• Europium(III) Triflate-Catalyzed Trofimov Synthesis of Polyfunctionalized Pyrroles
  作者：Sridhar Madabhushi、Venkata Sairam Vangipuram、Kishore Kumar Reddy Mallu、Narsaiah Chinthala、China Ramanaiah Beeram

  DOI：10.1002/adsc.201200036

  日期：2012.5.21

  The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described.

  描述了通过使用三氟甲磺酸euro（III）作为催化剂，使酮肟与乙炔二甲酸二甲酯反应来合成多官能吡咯。
• Furan and pyrrole containing lipoxygenase inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05112848A1

  公开（公告）日：1992-05-12

  Substituted furan and pyrrole compounds which are useful in inhibiting lipoxygenase enzymes, particularly 5-lipoxygenase.

  替代呋喃和吡咯化合物可用于抑制脂氧合酶酶，特别是5-脂氧合酶。
• Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac
  作者：Nitin L Jadhao、Harish B. Musale、Jayant M. Gajbhiye、Vivek T. Humne

  DOI：10.1039/d3ob01882b

  日期：——

  A new protocol for the direct synthesis of 2-aminothiazole has been developed from oxime acetate and readily available sodium thiocyanate using a copper catalyst. The present transformation has good functional group tolerance. Various thiazoles were smoothly synthesized in good to excellent yields. The applicability of the present method has been extended to the formal synthesis of the non-steroidal

  使用铜催化剂，由乙酸肟和容易获得的硫氰酸钠开发了一种直接合成 2-氨基噻唑的新方案。本转化具有良好的官能团耐受性。各种噻唑类化合物均以良好至优异的产率顺利合成。本方法的适用性已扩展到通过桑德迈尔反应和铃木偶联来正式合成非甾体抗炎药芬替扎克。
• Structure−Activity Relationships of <i>N</i>-Hydroxyurea 5-Lipoxygenase Inhibitors
  作者：Andrew O. Stewart、Pramila A. Bhatia、Jonathan G. Martin、James B. Summers、Karen E. Rodriques、Michael B. Martin、James H. Holms、Jimmie L. Moore、Richard A. Craig、Teodozyj Kolasa、James D. Ratajczyk、Hormoz Mazdiyasni、Francis A. J. Kerdesky、Shari L. DeNinno、Robert G. Maki、Jennifer B. Bouska、Patrick R. Young、Carmine Lanni、Randy L. Bell、George W. Carter、Clint D. W. Brooks

  DOI：10.1021/jm9700474

  日期：1997.6.1

  The discovery of second generation N-hydroxyurea 5-lipoxygenase inhibitors was accomplished through the development of a broad structure-activity relationship (SAR) study. This study identified requirements for improving potency and also extending duration by limiting metabolism. Potency could be maintained by the incorporation of heterocyclic templates substituted with selected lipophilic substituents. Duration of inhibition after oral administration was optimized by identification of structural features in the proximity of the N-hydroxyurea which correlated to low in vitro glucuronidation rates. Furthermore, the rate of in vitro glucuronidation was shown to be stereoselective for certain analogs. (R)-N-[3-[5-(4-Fluorophenoxy)-2-furyl]-1-methyl-2-propynyl]-N-hy- droxyurea (17c) was identified and selected for clinical development.