N-hydroxy-4-methylpent-4-enamide | 1159991-85-1

• 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-4-methylpent-4-enamide
• CAS: 1159991-85-1
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RJOHPMKOXZDQMB-UHFFFAOYSA-N

物化性质

• 密度：
  1.025±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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-4-methylpent-4-enamide 在 1,10-菲罗啉 、 叠氮基三甲基硅烷 、 iron(II) acetate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 5-(azidomethyl)-5-methylpyrrolidin-2-one
  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
• 作为产物：
  描述：

  4-甲基-4-戊酸 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-4-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

• Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes
  作者：Honghui Lei、John H. Conway、Caleb C. Cook、Tomislav Rovis

  DOI：10.1021/jacs.9b06366

  日期：2019.7.31

  An intramolecular Ir(III)-catalyzed regiodivergent oxyamination of unactivated alkenes provides valuable γ-lactams, γ-lactones and δ-lactams. The regioselectivity is controlled by the electronically tunable cyclopentadienyl Ir(III)-complexes enabling oxyamination via either 5-exo or 6-endo pathways. With respect to the mechanism, we propose a highly reactive [3.1.0] bicycle intermediate derived from

  未活化烯烃的分子内 Ir(III) 催化区域发散氧化胺化提供有价值的 γ-内酰胺、γ-内酯和 δ-内酰胺。区域选择性由电子可调的环戊二烯基 Ir(III)-络合物控制，该络合物能够通过 5-exo 或 6-endo 途径进行氧胺化。在机制方面，我们提出了一种源自 Ir(V) 氮烯介导的氮丙啶化的高反应性 [3.1.0] 自行车中间体，作为合成 γ-内酰胺的关键中间体。
• 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。