(4-fluorophenyl)[(2-phenylethyl)amino]acetonitrile | 154319-58-1

• 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: (4-fluorophenyl)[(2-phenylethyl)amino]acetonitrile
• 英文别名: N-(2-Phenethyl)-α-cyano-p-fluorobenzylamine；2-(4-fluorophenyl)-2-(phenethylamino)acetonitrile；2-(4-Fluorophenyl)-2-(2-phenylethylamino)acetonitrile
• CAS: 154319-58-1
• 化学式: C₁₆H₁₅FN₂
• 分子量: 254.307
• InChiKey: TWFBWGAEWYEPPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-fluorophenyl)[(2-phenylethyl)amino]acetonitrile 在 盐酸 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 52.72h， 生成 dichloro[bis[5-(4-chlorophenyl)-4-(4-fluorophenyl)-1-(4-methylphenyl)-3-(2-phenylethyl)(2-¹³C)-1,3-dihydro-2H-imidazol-2-ylidene]]platinum(II)
  参考文献：
  名称：

  Synthesis of Highly Substituted 2-13C-Imidazolium Salts and Metal NHC ­Complexes for the Investigation of Electronic Unsymmetry by NMR

  摘要：

  Complexes of unsymmetrically substituted N-heterocyclic carbenes with NMR-active metals (Ag, Hg, Pt) with or without a C-13-label in the 2-position were synthesized by aldimine cross coupling and analyzed with respect to the scalar couplings between the metal center or C2 and the other ring atoms.

  DOI：

  10.1055/s-0033-1338496
• 作为产物：
  描述：

  potassium cyanide 、 对氟苯甲醛 、 2-苯乙胺 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以66%的产率得到(4-fluorophenyl)[(2-phenylethyl)amino]acetonitrile
  参考文献：
  名称：

  Synthesis of Highly Substituted 2-13C-Imidazolium Salts and Metal NHC ­Complexes for the Investigation of Electronic Unsymmetry by NMR

  摘要：

  Complexes of unsymmetrically substituted N-heterocyclic carbenes with NMR-active metals (Ag, Hg, Pt) with or without a C-13-label in the 2-position were synthesized by aldimine cross coupling and analyzed with respect to the scalar couplings between the metal center or C2 and the other ring atoms.

  DOI：

  10.1055/s-0033-1338496

文献信息

• Synthesis of 1,2-Disubstituted Indoles from α-Aminonitriles and 2-Halobenzyl Halides
  作者：Anne-Katrin Bachon、Till Opatz

  DOI：10.1021/acs.joc.5b02659

  日期：2016.3.4

  The α-alkylation of deprotonated Strecker products derived from primary amines and aromatic aldehydes with 2-halobenzyl halides furnishes intermediates that can be cyclized to 1,2-disubstituted indoles in moderate to high yields (up to 94% over two steps) by microwave-assisted copper- or palladium-catalyzed intramolecular cross-coupling.

  由伯胺和芳族醛衍生的去质子化的Strecker产品与2-卤代苄基卤化物的α-烷基化提供了中间体，该中间体可以通过微波-以中等至高收率（分两步收率高达94％）环化为1,2-二取代的吲哚。辅助铜或钯催化的分子内交叉偶联。
• Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides, .alpha.-Acylamino Carboxamides, Imidazolinones, and Hydantoins
  作者：Jean-Pierre Leblanc、Harry W. Gibson

  DOI：10.1021/jo00084a025

  日期：1994.3

  Acyclic Reissert compounds 2 and bis(Reissert compound)s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate cr-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of alpha-amino carboxamides 9, whereas substituted analogs 7 undergo cyclization to imidazolinones 11. Hydrogen peroxide treatment of alpha-cyano carbamate Reissert compounds, substituted (13) or not (12), affords substituted hydantoins 14.