N-[(S)-1-(1-naphthyl)ethyl]-2-fluoroaniline | 1188926-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(S)-1-(1-naphthyl)ethyl]-2-fluoroaniline
• 英文别名: 2-fluoro-N-[(1S)-1-naphthalen-1-ylethyl]aniline
• CAS: 1188926-66-0
• 化学式: C₁₈H₁₆FN
• 分子量: 265.33
• InChiKey: GTAGILABXJRQQY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 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：
  2

反应信息

• 作为反应物：
  描述：

  N-[(S)-1-(1-naphthyl)ethyl]-2-fluoroaniline 、 potassium diphenylphosphine 以 1,4-二氧六环 为溶剂， 反应 120.0h， 以52%的产率得到N-[(S)-1-(1-naphthyl)ethyl]-2-diphenylphosphinoaniline
  参考文献：
  名称：

  高效，多功能的膦-亚磷酰胺配体，用于不对称加氢

  摘要：

  Abstractmagnified imageA set of novel phosphine‐phosphoramidite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐phenylethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1a] and (11bR)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(1‐naphthyl)ethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1b] are unique in providing enantioselectivities ≥96% ee and ≥94% ee, respectively, in mechanistically distinct hydrogenations of CC, CN and CO double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respectively). Particularly remarkable are the enantiomeric excesses up to 97% achieved in the iridium‐catalyzed hydrogenation of 2‐substituted quinolines, where (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(naphthalen‐1‐yl)ethyl]‐8,9,10,11, 12,13,14,15‐octahydrodinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐2] proved to be the most selective ligand. Substantially lower ees were obtained with the mismatched diastereomer (Ra,Sc)‐1b and with the N‐phenyl‐substituted ligand 1c, missing a second element of chirality.

  DOI：

  10.1002/adsc.200800653
• 作为产物：
  描述：

  邻溴氟苯 、 (S)-(-)-1-(1-萘基)乙胺 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以93%的产率得到N-[(S)-1-(1-naphthyl)ethyl]-2-fluoroaniline
  参考文献：
  名称：

  高效，多功能的膦-亚磷酰胺配体，用于不对称加氢

  摘要：

  Abstractmagnified imageA set of novel phosphine‐phosphoramidite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐phenylethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1a] and (11bR)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(1‐naphthyl)ethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1b] are unique in providing enantioselectivities ≥96% ee and ≥94% ee, respectively, in mechanistically distinct hydrogenations of CC, CN and CO double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respectively). Particularly remarkable are the enantiomeric excesses up to 97% achieved in the iridium‐catalyzed hydrogenation of 2‐substituted quinolines, where (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(naphthalen‐1‐yl)ethyl]‐8,9,10,11, 12,13,14,15‐octahydrodinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐2] proved to be the most selective ligand. Substantially lower ees were obtained with the mismatched diastereomer (Ra,Sc)‐1b and with the N‐phenyl‐substituted ligand 1c, missing a second element of chirality.

  DOI：

  10.1002/adsc.200800653

文献信息

• Highly Efficient and Versatile Phosphine-Phosphoramidite Ligands for Asymmetric Hydrogenation
  作者：Matthias Eggenstein、Anika Thomas、Jens Theuerkauf、Giancarlo Franciò、Walter Leitner

  DOI：10.1002/adsc.200800653

  日期：2009.3

  Abstractmagnified imageA set of novel phosphine‐phosphoramidite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐phenylethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1a] and (11bR)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(1‐naphthyl)ethyl]dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐1b] are unique in providing enantioselectivities ≥96% ee and ≥94% ee, respectively, in mechanistically distinct hydrogenations of CC, CN and CO double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respectively). Particularly remarkable are the enantiomeric excesses up to 97% achieved in the iridium‐catalyzed hydrogenation of 2‐substituted quinolines, where (11bS)‐N‐[2‐(diphenylphosphino)phenyl]‐N‐[(S)‐1‐(naphthalen‐1‐yl)ethyl]‐8,9,10,11, 12,13,14,15‐octahydrodinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin‐4‐amine [(Sa,Sc)‐2] proved to be the most selective ligand. Substantially lower ees were obtained with the mismatched diastereomer (Ra,Sc)‐1b and with the N‐phenyl‐substituted ligand 1c, missing a second element of chirality.