(S)-2-苯基-2-对甲苯氨基乙醇 | 572923-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-2-苯基-2-对甲苯氨基乙醇
• 中文别名: 4-(5-氨基-苯并恶唑-2-基)-苯酚
• 英文名称: 2-phenyl-2-(p-tolylamino)ethanol
• 英文别名: (S)-2-Phenyl-2-p-tolylamino-ethanol；(2S)-2-(4-methylanilino)-2-phenylethanol
• CAS: 572923-26-3
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: KFMIAGTVOCCVST-OAHLLOKOSA-N

物化性质

• 沸点：
  385.2±27.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4-苯基-2-恶唑烷酮 在 sodium hydroxide 、 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 2-(二叔丁基膦)联苯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 17.67h， 生成 (S)-2-苯基-2-对甲苯氨基乙醇
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of N-Aryloxazolidinones from Aryl Chlorides

  摘要：

  An efficient method for intermolecular N-arylation of oxazolidinones using Pd(2)dba(3) and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl beta-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.

  DOI：

  10.1021/ol034428p

文献信息

• Magnetic Nano Fe3O4 Catalyzed Solvent-Free Stereo- and Regioselective ­Aminolysis of Epoxides by Amines; a Green Method for the Synthesis of β-Amino Alcohols
  作者：Srinivasarao Babu、Amit Kumar、Ramarao Parella

  DOI：10.1055/s-0033-1340844

  日期：——

  We report the use of magnetic nano Fe3O4 as a mild heterogeneous catalyst for the aminolysis of epoxides with amines. The approach constitutes a green method for the formation of a variety of β-amino alcohols with very high stereo- and regioselectivity under solvent-free and ambient reaction conditions. The aminolysis of chiral epoxides with amines gave the corresponding chiral β-amino alcohols with

  我们报告了使用磁性纳米 Fe3O4 作为温和的多相催化剂，用于环氧化物与胺的氨解。该方法构成了一种在无溶剂和环境反应条件下形成具有非常高立体选择性和区域选择性的各种 β-氨基醇的绿色方法。手性环氧化物与胺的氨解得到相应的手性 β-氨基醇，立体化学完全反转。磁性纳米Fe3O4催化剂易于回收和循环利用。
• Asymmetric opening of styrene oxide with p-toluidine catalyzed by BINOL polyols and their lithium complexes
  作者：Yu. N. Belokon’、V. I. Maleev、M. A. Moskalenko、Yu. V. Samoilichenko、A. S. Peregudov、A. T. Tsaloev

  DOI：10.1007/s11172-013-0195-x

  日期：2013.6

  Opening of racemic styrene oxide with p-toluidine catalyzed by chiral BINOL-derived polyols proceeded regioselectively mainly with the formation of 2-phenyl-2-(p-tolylamino)-ethanol with low ee values.

  由手性 BINOL 衍生的多元醇催化的外消旋氧化苯乙烯与对甲苯胺的开环主要是区域选择性地进行，主要是形成具有低 ee 值的 2-苯基-2-（对甲苯基氨基）-乙醇。
• Palladium-Catalyzed Synthesis of <i>N-</i>Aryloxazolidinones from Aryl Chlorides
  作者：Arun Ghosh、Janice E. Sieser、Maxime Riou、Weiling Cai、Luis Rivera-Ruiz

  DOI：10.1021/ol034428p

  日期：2003.6.1

  An efficient method for intermolecular N-arylation of oxazolidinones using Pd(2)dba(3) and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl beta-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.