N-(4-phenylbut-2-enyl)aniline | 855595-39-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-phenylbut-2-enyl)aniline
• CAS: 855595-39-0
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: OHMSLECGYNATPB-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±21.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  buta-2,3-dienyl-benzene 、 苯胺 在 gold(III) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以80%的产率得到N-(4-phenylbut-2-enyl)aniline
  参考文献：
  名称：

  Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight

  摘要：

  A wide range of nucleophiles, such as amines and alcohols, reacted intermolecularly with various allenes in the presence of gold catalysts to give the corresponding hydrofunctionalization products in high yields. The intermolecular hydroamination of chiral allenes with aromatic and aliphatic amines proceeded with high to good enantioface selectivities to afford the corresponding chiral allylic amines. On the other hand, in the case of the intermolecular hydroalkoxylation of chiral allenes, no chirality transfer was observed. This marked contrast on the chirality transfer indicates that the mechanisms of gold-catalysis between hydroamination and hydroalkoxylation are different. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.11.106

文献信息

• Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd–PHOX Catalyst
  作者：Nathan J. Adamson、Ethan Hull、Steven J. Malcolmson

  DOI：10.1021/jacs.7b03480

  日期：2017.5.31

  We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active

  我们报告了一种将脂肪胺催化、对映选择性分子间加成到无环 1,3-二烯的方法。在大多数情况下，在 5 mol% 的带有 PHOX 配体的 Pd 催化剂的存在下，反应在室温或低于室温下有效地进行，生成烯丙胺高达 97:3 er。配体中缺电子膦的存在不仅会导致催化剂更具活性，而且对于在转化中实现高位点选择性也至关重要。