N-(2-(sec-butyl(hydroxy)amino)propyl)prop-2-en-1-amine | 1349708-39-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-(sec-butyl(hydroxy)amino)propyl)prop-2-en-1-amine
• 英文别名: N-(1-(allylamino)propan-2-yl)-N-hydroxybutan-2-amine；N-butan-2-yl-N-[1-(prop-2-enylamino)propan-2-yl]hydroxylamine
• CAS: 1349708-39-9
• 化学式: C₁₀H₂₂N₂O
• 分子量: 186.297
• InChiKey: AYNBYOHNZDKPOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(sec-butyl)hydroxylamine 、 二烯丙基胺 在 苄氧基乙醛 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以61%的产率得到N-(2-(sec-butyl(hydroxy)amino)propyl)prop-2-en-1-amine
  参考文献：
  名称：

  催化束缚策略：简单的醛催化分子间烯烃氢胺化

  摘要：

  在本文中，我们描述了一种催化束缚策略，其中简单的醛预催化剂通过临时分子内、室温分子间加氢胺化反应和邻二胺的合成来实现。该催化剂允许由烯丙胺和羟胺形成混合胺醛，从而导致容易的分子内加氢胺化事件。用手性醛获得的有希望的对映选择性也突出了这种催化束缚方法在不对称催化中的潜力，并证明仅依赖临时分子内的有效对映诱导是可能的。

  DOI：

  10.1021/ja208867g

文献信息

• Catalysis through Temporary Intramolecularity: Mechanistic Investigations on Aldehyde-Catalyzed Cope-type Hydroamination Lead to the Discovery of a More Efficient Tethering Catalyst
  作者：Nicolas Guimond、Melissa J. MacDonald、Valérie Lemieux、André M. Beauchemin

  DOI：10.1021/ja303320x

  日期：2012.10.10

  Mechanistic investigations on the aldehyde-catalyzed intermolecular hydroamination of allylic amines using N-alkylhydroxylamines are presented. Under the reaction conditions, the presence of a specific aldehyde catalyst allows formation of a mixed aminal intermediate, which permits intramolecular Cope-type hydroamination. The reaction was determined to be first-order in both the aldehyde catalyst (alpha-benzyloxyacetaldehyde) and the allylic amine. However, the reaction displays an inverse order behavior in benzylhydroxylamine, which reveals a significant off-cycle pathway and highlights the importance of an aldehyde catalyst that promotes a reversible aminal formation. Kinetic isotope effect experiments suggest that hydroamination is the rate-limiting step of this catalytic cycle. Overall, these results enabled the elaboration of a more accurate catalytic cycle and led to the development of a more efficient catalytic system for alkene hydroamination. The use of 5-10 mol % of paraformaldehyde proved more effective than the use of 20 mol % of a-benzyloxyacetaldehyde, leading to high yields of intermolecular hydroamination products within 24 h at 30 degrees C.