N-benzyl-N-[phenyl(pyrimidin-2-yl)methyl]amine | 1161432-26-3

• 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: N-benzyl-N-[phenyl(pyrimidin-2-yl)methyl]amine
• 英文别名: N-Benzyl-1-phenyl-1-(pyrimidin-2-yl)methanamine；N-benzyl-1-phenyl-1-pyrimidin-2-ylmethanamine
• CAS: 1161432-26-3
• 化学式: C₁₈H₁₇N₃
• 分子量: 275.353
• InChiKey: RYXYLOUWMHQXTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  417.9±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate(II) 、 N-benzyl-N-[phenyl(pyrimidin-2-yl)methyl]amine 以 甲醇 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  N‐Heterocyclic Benzhydrylamines as New N , N ‐Bidentate Ligands in Palladium Complexes: Synthesis, Characterization and Catalytic Activity

  摘要：

  AbstractThe synthesis of new N,N‐bidentate ligands based on a π‐deficient N‐heterocyclic benzhydrylamine core is described. The corresponding air‐stable palladium complexes are obtained in high yields and fully characterized by NMR spectroscopy and X‐ray structure determination. These new phosphane‐free catalytic systems proved efficient in the Suzuki–Miyaura reaction, enabling us to obtain biaryl products in good yields, also for reactions with o‐substituted phenyl chlorides as starting materials. The effects of both electronic and steric modulations at the benzhydrylamine core on the catalytic activity are also described.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejic.200800154
• 作为产物：
  描述：

  2-氰基嘧啶 、 苯基氯化镁 在 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-benzyl-N-[phenyl(pyrimidin-2-yl)methyl]amine
  参考文献：
  名称：

  N-杂环吡啶甲基甲胺：合成，络合，分子结构及其在不对称铃木-宫浦和氧化偶联反应中的应用

  摘要：

  描述了基于π-缺陷的N-杂环吡啶基甲胺核的N，N-二齿配体的合成。说明了溶液和固态中相应的N，N-配体-钯配合物的制备和表征。Pd配合物在不对称的Suzuki-Miyaura偶联反应中显示出良好的收率和中等的催化活性（高达40％ee），从而导致了甲氧基双萘基衍生物。N，N-吡啶基甲胺与碘化亚铜的组合显示了氧化萘酚衍生物偶联反应中的有效催化体系，以高收率提供了相应的联萘，对映选择性高达61％。

  DOI：

  10.1021/om200375s

文献信息

• N‐Heterocyclic Benzhydrylamines as New <i>N</i> , <i>N</i> ‐Bidentate Ligands in Palladium Complexes: Synthesis, Characterization and Catalytic Activity
  作者：Vincent Terrasson、Damien Prim、Jérome Marrot

  DOI：10.1002/ejic.200800154

  日期：2008.6

  AbstractThe synthesis of new N,N‐bidentate ligands based on a π‐deficient N‐heterocyclic benzhydrylamine core is described. The corresponding air‐stable palladium complexes are obtained in high yields and fully characterized by NMR spectroscopy and X‐ray structure determination. These new phosphane‐free catalytic systems proved efficient in the Suzuki–Miyaura reaction, enabling us to obtain biaryl products in good yields, also for reactions with o‐substituted phenyl chlorides as starting materials. The effects of both electronic and steric modulations at the benzhydrylamine core on the catalytic activity are also described.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• N-Heterocyclic Pyridylmethylamines: Synthesis, Complexation, Molecular Structure, and Application to Asymmetric Suzuki–Miyaura and Oxidative Coupling Reactions
  作者：Guillaume Grach、Grégory Pieters、Aurelia Dinut、Vincent Terrasson、Raouf Medimagh、Alexandre Bridoux、Vanessa Razafimahaleo、Anne Gaucher、Sylvain Marque、Jérôme Marrot、Damien Prim、Richard Gil、José Giner Planas、Clara Viñas、Isabelle Thomas、Jean-Philippe Roblin、Yves Troin

  DOI：10.1021/om200375s

  日期：2011.8.8

  The synthesis of N,N-bidentate ligands based on a π-deficient N-heterocyclic pyridylmethylamine core is described. The preparation and characterization of the corresponding N,N-ligand–palladium complexes in solution and the solid state are illustrated. Pd complexes showed a good yield and moderate catalytic activity (up to 40% ee) in the asymmetric Suzuki–Miyaura coupling reaction, leading to methoxybinaphthyl

  描述了基于π-缺陷的N-杂环吡啶基甲胺核的N，N-二齿配体的合成。说明了溶液和固态中相应的N，N-配体-钯配合物的制备和表征。Pd配合物在不对称的Suzuki-Miyaura偶联反应中显示出良好的收率和中等的催化活性（高达40％ee），从而导致了甲氧基双萘基衍生物。N，N-吡啶基甲胺与碘化亚铜的组合显示了氧化萘酚衍生物偶联反应中的有效催化体系，以高收率提供了相应的联萘，对映选择性高达61％。