N-hydroxy-3-methylpent-4-enamide | 1159991-90-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-hydroxy-3-methylpent-4-enamide
• CAS: 1159991-90-8
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: NXFYXLYKRHOZOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-3-methylpent-4-enamide 、 2,4,6-三甲基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以1.35 g的产率得到N-[(mesitylcarbonyl)oxy]-3-methylpent-4-enamide
  参考文献：
  名称：

  酰胺的束缚氨基羟基化（TA）反应

  摘要：

  据报道，催化的酰胺束缚的氨基羟基化反应的第一个例子表明，使用基于N-O的再氧化剂对成功至关重要。所描述的系统与多种不同的烯烃取代方式和环大小兼容，并且在环状和非环状系统中均以低负荷运行。对于在有机合成中使用立体选择性TA反应而言，对于在烯丙基和烯丙基位置上的取代基都观察到的非对映选择性水平很好。

  DOI：

  10.1021/ol900631y
• 作为产物：
  描述：

  3-甲基-4-戊烯酸 在 咪唑 、 盐酸羟胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N-hydroxy-3-methylpent-4-enamide
  参考文献：
  名称：

  Iron-Catalyzed Intra-intermolecular Aminoazidation of Alkenes

  摘要：

  An intra-intermolecular iron-catalyzed aminoazidation of non-activated alkenes is reported for the preparation of imidazolidinone, oxazolidinone, and pyrrolidinone derivatives. The method uses cheap and abundant iron as a catalyst and commercially available TMSN3 as an azide source. This domino process allows, in a single operating step, for a ring-closure that generates an aza-heterocycle and the introduction of an azido appendage tethered to the heterocycle. The conditions developed offer a sustainable alternative method for the preparation of unsymmetrical vicinal diamine compounds.

  DOI：

  10.1021/acs.oprd.9b00400

文献信息

• HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS ANTI-INFLAMMATORY COMPOUNDS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0652864A1

  公开（公告）日：1995-05-17
• [EN] HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS ANTI-INFLAMMATORY COMPOUNDS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE ET LEUR UTILISATION A TITRE DE COMPOSES ANTI-INFLAMMATOIRES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1994002448A1

  公开（公告）日：1994-02-03

  (EN) The present invention is concerned with novel hydroxamic acid derivatives of formula (I) and their use in medical therapy, particularly in the treatment of a clinical condition for which an inhibitor of the lipoxygenase or cyclooxygenase mediated arachadonic acid metabolic pathway is indicated. The invention also relates to pharmaceutical formulations and processes for the preparation of compounds according to the invention.(FR) L'invention concerne de nouveaux dérivés d'acide hydroxamique de formule (I), et leur utilisation dans la thérapie médicale, surtout dans le cas de traitement d'une affection clinique pour laquelle est indiqué un inhibiteur de la voie d'acide arachadonique à médiation par la lipoxygénase ou la cyclooxygénase. L'invention concerne également des formulations pharmaceutiques ainsi que des procédés de préparation des composés décrits.
• Tethered Aminohydroxylation (TA) Reaction of Amides
  作者：Timothy J. Donohoe、Cedric K. A. Callens、Amber L. Thompson

  DOI：10.1021/ol900631y

  日期：2009.6.4

  The first examples of amide-tethered aminohydroxylation reactions, catalyzed by osmium, showing that the use of N−O-based reoxidants are essential for success, are reported. The system that is described is compatible with a variety of different alkene substitution patterns and ring sizes and works with low loadings in both cyclic and acyclic systems. The levels of diastereoselectivity that were observed

  据报道，催化的酰胺束缚的氨基羟基化反应的第一个例子表明，使用基于N-O的再氧化剂对成功至关重要。所描述的系统与多种不同的烯烃取代方式和环大小兼容，并且在环状和非环状系统中均以低负荷运行。对于在有机合成中使用立体选择性TA反应而言，对于在烯丙基和烯丙基位置上的取代基都观察到的非对映选择性水平很好。
• Iron-Catalyzed Intra-intermolecular Aminoazidation of Alkenes
  作者：Sandra Abi Fayssal、Alessandro Giungi、Farouk Berhal、Guillaume Prestat

  DOI：10.1021/acs.oprd.9b00400

  日期：2020.5.15

  An intra-intermolecular iron-catalyzed aminoazidation of non-activated alkenes is reported for the preparation of imidazolidinone, oxazolidinone, and pyrrolidinone derivatives. The method uses cheap and abundant iron as a catalyst and commercially available TMSN3 as an azide source. This domino process allows, in a single operating step, for a ring-closure that generates an aza-heterocycle and the introduction of an azido appendage tethered to the heterocycle. The conditions developed offer a sustainable alternative method for the preparation of unsymmetrical vicinal diamine compounds.