N-(2-propylpiperidin-1-yl)benzamide | 1159092-10-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: N-(2-propylpiperidin-1-yl)benzamide
• CAS: 1159092-10-0
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: IEAGEMSEPHPNQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-((E)-oct-5-enyl)benzohydrazide 以 三氟甲苯 为溶剂， 反应 19.0h， 生成 N-(2-propylpiperidin-1-yl)benzamide
  参考文献：
  名称：

  Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation

  摘要：

  Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200 degrees C, and the tatter reaction is shown to be stereospecific.

  DOI：

  10.1021/ja902558j

文献信息

• Improved Cope-type hydroamination reactivity of hydrazine derivatives
  作者：Francis Loiseau、Christian Clavette、Michaël Raymond、Jean-Grégoire Roveda、Alishya Burrell、André M. Beauchemin

  DOI：10.1039/c0cc02403a

  日期：——

  A systematic investigation on the metal-free, Cope-type hydroamination reactivity of hydrazides and analogues is reported. Optimization of the hydrazide structure resulted in more facile intramolecular reactivity and enabled intermolecular reactions of alkenes, thus providing a direct approach to polysubstituted hydrazides.

  报道了对无金属、Cope型偶氮胺反应性的肼羧酸及其类似物的系统研究。优化肼羧酸结构使分子内反应更加容易，并实现了烯烃的分子间反应，从而提供了一种直接制备多取代肼羧酸的方法。
• Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation
  作者：Jean-Grégoire Roveda、Christian Clavette、Ashley D. Hunt、Serge I. Gorelsky、Christopher J. Whipp、André M. Beauchemin

  DOI：10.1021/ja902558j

  日期：2009.7.1

  Benzoic hydrazides (R = Ph), which are remarkably bench and thermally stable reagents (often up to 230 degrees C), afford intramolecular hydroamination products upon heating at high temperatures (120-235 degrees C). A concerted Cope-type hydroamination event, followed by a hydrazide-mediated proton transfer step of the hydrazinium ylide intermediate, is proposed and supported by DFT calculations. In contrast, a simple modification of the reagent structure (R = Ot-Bu or NH2) favors the formation of aminocarbonylation products at 200 degrees C, and the tatter reaction is shown to be stereospecific.