3-acetylfuran oxime

• 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: 3-acetylfuran oxime
• 英文别名: 3-Acetylfuran oxime；N-[1-(furan-3-yl)ethylidene]hydroxylamine
• 化学式: C₆H₇NO₂
• 分子量: 125.127
• InChiKey: GZKAVGTVBPEXFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3-acetylfuran oxime 在 盐酸 、 吡啶硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 1-(1-呋喃-3-基乙基)-1-羟基脲
  参考文献：
  名称：

  Structure−Activity Relationships of N-Hydroxyurea 5-Lipoxygenase Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm9700474

文献信息

• Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box)ReV-Oxo Complexes
  作者：Kristine A. Nolin、Richard W. Ahn、Yusuke Kobayashi、Joshua J. Kennedy-Smith、F. Dean Toste

  DOI：10.1002/chem.201001164

  日期：2010.8.16

  application of chiral, non‐racemic ReV–oxo complexes to the enantioselective reduction of prochiral ketones is described. In addition to the enantioselective reduction of prochiral ketones, we report the application of these complexes to 1) a tandem Meyer–Schuster rearrangement/reduction to access enantioenriched allylic alcohols and 2) the enantioselective reduction of imines.

  描述了手性非外消旋 Re V - oxo 配合物在前手性酮的对映选择性还原中的开发和应用。除了前手性酮的对映选择性还原外，我们还报告了这些复合物在以下方面的应用：1）串联 Meyer-Schuster 重排/还原以获取对映体富集的烯丙醇和 2）亚胺的对映选择性还原。
• Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex
  作者：Kristine A. Nolin、Richard W. Ahn、F. Dean Toste

  DOI：10.1021/ja050831a

  日期：2005.9.1

  An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)-oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium-oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), alpha-iminoesters, and alpha,beta-unsaturated imines are reduced with good to excellent enantioselectivities.
• Synthesis of 3-substituted furylethylamines
  作者：N. E. Shevchenko

  DOI：10.1007/bf02251702

  日期：1999.2
• 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.