N-(1-呋喃-2-乙基)羟胺 | 123606-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: N-(1-呋喃-2-乙基)羟胺
• 中文别名: N-(1-呋喃-2-基-乙基)-羟胺
• 英文名称: N-(1-(furan-2-yl)ethyl)hydroxylamine
• 英文别名: N-[1-(furan-2-yl)ethyl]hydroxylamine
• CAS: 123606-36-0
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: YZFFDDLGEYKSJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  三甲基硅基异氰酸酯 、 N-(1-呋喃-2-乙基)羟胺 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 N-hydroxy-N-(1-fur 2-ylethyl) urea
  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
• 作为产物：
  描述：

  (E)-1-(furan-2-yl)ethanone oxime 在 甲酸 、 C₁₈H₂₄ClIrN₃⁽¹⁺⁾*Cl^(1-) 、 sodium formate 、 三氟乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以26 %的产率得到N-(1-呋喃-2-乙基)羟胺
  参考文献：
  名称：

  铱催化肟转移加氢合成N-烷氧基胺和羟胺

  摘要：

  发现阳离子铱（Ir）配合物催化肟的转移加氢以得到N-烷氧基胺和羟胺，并且三氟乙酸加速了反应。该协议的实际应用通过克级转化和杀菌剂 furmecyclox (BAS 389F) 的两步合成得到证明，总产量分别为 92% 和 85%。证明了使用手性 Ir 配合物提供手性N-烷氧基胺的不对称方案，但获得的低产率/ee 表明需要进一步开发。

  DOI：

  10.1039/d2ob01084d

文献信息

• 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.
• Synthesis of <i>N</i>-alkoxy amines and hydroxylamines <i>via</i> the iridium-catalyzed transfer hydrogenation of oximes
  作者：Yanping Xia、Sen Wang、Rui Miao、Jianhua Liao、Lu Ouyang、Renshi Luo

  DOI：10.1039/d2ob01084d

  日期：——

  hydrogenation of oximes to access N-alkoxy amines and hydroxylamines, and the reaction was accelerated by trifluoroacetic acid. The practical application of this protocol was demonstrated by a gram-scale transformation and two-step synthesis of the fungicide furmecyclox (BAS 389F) in overall yields of 92 and 85%, respectively. An asymmetric protocol using chiral Ir complexes to afford chiral N-alkoxy amines was

  发现阳离子铱（Ir）配合物催化肟的转移加氢以得到N-烷氧基胺和羟胺，并且三氟乙酸加速了反应。该协议的实际应用通过克级转化和杀菌剂 furmecyclox (BAS 389F) 的两步合成得到证明，总产量分别为 92% 和 85%。证明了使用手性 Ir 配合物提供手性N-烷氧基胺的不对称方案，但获得的低产率/ee 表明需要进一步开发。