(R)-(+)-2-萘基-(1-苯基乙基)胺 | 1009807-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-(+)-2-萘基-(1-苯基乙基)胺
• 英文名称: (R)-(+)-2-naphthyl-(1-phenylethyl)amine
• 英文别名: N-[(1R)-1-phenylethyl]naphthalen-2-amine
• CAS: 1009807-63-9
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: GVRPFOISEZNPLT-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-萘基三氟甲烷磺酸 、 R(+)-alpha-甲基苄胺 在 tris(dibenzylideneacetone)dipalladium (0) potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 (R)-(+)-2-萘基-(1-苯基乙基)胺 、 (S)-2-naphthyl-(1-phenylethyl)amine
  参考文献：
  名称：

  Steric effects in palladium-catalysed amination of aryl triflates and nonaflates with the primary amines PhCH(R)NH2 (R=H, Me)

  摘要：

  A systematic study of the effects of aryl triflate and nonaflate structure on the yield of amination with the primary amines PhCH(R)NH2 (R=H, Me) under palladium catalysis has been carried out. High throughput screening indicated that a catalyst composed of X-Phos/Pd-2(dba)(3)/1.4-dioxane was optimal based on a model reaction of Ar(ORf) [R-f-T-f (SO2CF3) Nf (SO2(CF2)(3)CF3)] with PhCH2NH2. Comparisons of the reactivity of various ArOTf and ArONf [Ar=4-MePh, 2-naphthyl, 1-naphthyl, 2-PhC6H4] indicated that both ortho substitution in the aryl electrophile and at the alpha-position on the amine are detrimental to the coupling particularly when they occur in combination. Despite being formally a monodentate ligand use of X-Phos leads to only small degrees of racemisation when using (R)-PhCH(Me)NH2 (typically resulting in a reduction from 97 to 86-94% ee for the amine stereocentre). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.074

文献信息

• Steric effects in palladium-catalysed amination of aryl triflates and nonaflates with the primary amines PhCH(R)NH2 (R=H, Me)
  作者：Rebecca E. Meadows、Simon Woodward

  DOI：10.1016/j.tet.2007.11.074

  日期：2008.2

  A systematic study of the effects of aryl triflate and nonaflate structure on the yield of amination with the primary amines PhCH(R)NH2 (R=H, Me) under palladium catalysis has been carried out. High throughput screening indicated that a catalyst composed of X-Phos/Pd-2(dba)(3)/1.4-dioxane was optimal based on a model reaction of Ar(ORf) [R-f-T-f (SO2CF3) Nf (SO2(CF2)(3)CF3)] with PhCH2NH2. Comparisons of the reactivity of various ArOTf and ArONf [Ar=4-MePh, 2-naphthyl, 1-naphthyl, 2-PhC6H4] indicated that both ortho substitution in the aryl electrophile and at the alpha-position on the amine are detrimental to the coupling particularly when they occur in combination. Despite being formally a monodentate ligand use of X-Phos leads to only small degrees of racemisation when using (R)-PhCH(Me)NH2 (typically resulting in a reduction from 97 to 86-94% ee for the amine stereocentre). (c) 2007 Elsevier Ltd. All rights reserved.