2-(azepan-1-yl)-1-phenylpropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(azepan-1-yl)-1-phenylpropan-1-one
• 化学式: C₁₅H₂₁NO
• mdl: MFCD12647656
• 分子量: 231.338
• InChiKey: PKLXXRJADVQNCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己亚胺 、 苯丙酮 在 copper(ll) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.17h， 以82%的产率得到2-(azepan-1-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  Simple Catalytic Mechanism for the Direct Coupling of α-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix

  摘要：

  The direct alpha-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful alpha-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated alpha-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the alpha-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.

  DOI：

  10.1021/ja4096472

文献信息

• Simple Catalytic Mechanism for the Direct Coupling of α-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix
  作者：Ryan W. Evans、Jason R. Zbieg、Shaolin Zhu、Wei Li、David W. C. MacMillan

  DOI：10.1021/ja4096472

  日期：2013.10.30

  The direct alpha-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful alpha-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated alpha-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the alpha-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.