O-(2-phenylbut-3-enyl)hydroxylamine | 864722-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(2-phenylbut-3-enyl)hydroxylamine
• CAS: 864722-48-5
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: NGIZOFPVWUNYGG-UHFFFAOYSA-N

物化性质

• 沸点：
  280.2±29.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  O-(2-phenylbut-3-enyl)hydroxylamine 在 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 N-(3-hydroxy-1-methyl-2-phenylpropyl)acetamide
  参考文献：
  名称：

  Stereoselective Cyclization Reactions of IBX-Generated Alkoxyamidyl Radicals

  摘要：

  [GRAPHICS]In this paper, a method for the generation of alkoxyamidyl radicals is presented. These N-centered radicals can efficiently be formed starting from the corresponding acylated alkoxyamines using IBX as an oxidant. Stereoselective 5-exo and 6-exo reactions with these N-heteroatom-centered radicals leading to isoxazolidines and [1,2]oxazinanes are discussed. The N-O bond in the heterocycles can readily be cleaved with SmI2 to provide N-acylated 1,3-amino alcohols.

  DOI：

  10.1021/jo0509399
• 作为产物：
  描述：

  2-(2-Phenylbut-3-enoxy)isoindole-1,3-dione 在 一水合肼 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 O-(2-phenylbut-3-enyl)hydroxylamine
  参考文献：
  名称：

  铜催化烯烃氨基氧化立体选择性合成异恶唑烷

  摘要：

  异恶唑烷可用于有机合成、药物发现和化学生物学研究。公开了亚甲氧基取代的异恶唑烷的新立体选择性合成。该方法包括在 (2,2,6,6-四甲基哌啶-1-基)氧基自由基 (TEMPO) 和 O 2存在下铜催化的N-磺酰基-O-丁烯基羟胺的氨基氧化/环化，并提供取代的异恶唑烷优异的产率和非对映选择性。我们还展示了选择性单 N-O 还原，然后氧化剩余的 N-O 键以显示 2-氨基-γ-内酯。γ-内酯的还原揭示了相应的氨基二醇。

  DOI：

  10.1021/jo3013226

文献信息

• Stereoselective synthesis of the isoxazolidine ring <i>via</i> manganese(<scp>iii</scp>)-catalysed aminoperoxidation of unactivated alkenes using molecular oxygen in air under ambient conditions
  作者：Daisuke Yamamoto、Issei Hirano、Yuki Narushima、Masayuki Soga、Hiromasa Ansai、Kazuishi Makino

  DOI：10.1039/d2gc02205b

  日期：——

  In this study, we developed a route for the tris(mono-ferrocene-functionalised β-diketonato) manganese(III)-complex catalysed diastereoselective oxygenative aminoperoxidation of unactivated alkenes using molecular oxygen in air. In the reaction, ethanol is used as a solvent, and it proceeds at room temperature under open air. Due to its wide range of substrate scope, functional tolerance, simple operation

  在这项研究中，我们开发了一种利用空气中的分子氧对未活化烯烃进行三（单二茂铁-官能化 β-二酮）锰 ( III ) 络合物催化的非对映选择性含氧氨基过氧化反应的路线。该反应以乙醇为溶剂，在室温下露天进行。由于其广泛的底物范围、功能耐受性、操作简单以及温和环保的条件，该反应是一种很有前景的合成方法，可用于合成有价值的异恶唑烷环，不仅是天然产物中的特权结构，而且是 1,3- 的多功能合成子。氨基醇。
• Influence of Hydroxylamine Conformation on Stereocontrol in Pd-Catalyzed Isoxazolidine-Forming Reactions
  作者：Georgia S. Lemen、Natalie C. Giampietro、Michael B. Hay、John P. Wolfe

  DOI：10.1021/jo8027399

  日期：2009.3.20

  Palladium-catalyzed carboamination reactions between N-Boc-O-(but-3-enyl)hydroxylamine derivatives and aryl or alkenyl bromides afford cis-3,5- and trans-4,5-disubstituted isoxazolidines in good yield with up to >20:1 dr. The diastercoselectivity observed in the formation of cis-3,5-disubstituted isoxazolidines is superior to selectivities typically obtained in other transformations, such as 1,3-dipolar cycloaddition reactions, that provide these products. In addition, the stereocontrol in the C-N bond-forming Pd-catalyzed carboamination reactions of N-Boc-O-(but-3-enyl)hydroxylamines is significantly higher than that of related C-O bond-forming carboetherification reactions of N-benzyl-N-(but-3-enyl)hydroxylamine derivatives. This is likely due to a stereoelectronic preference for cyclization via transition states in which the Boc group is placed in a perpendicular orientation relative to the plane of the developing ring, which derives from the conformational equilibria of substituted hydroxylamines.