(S)-2-(2-naphthyl)-5-phenyl-1,3-oxazoline | 1245618-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(2-naphthyl)-5-phenyl-1,3-oxazoline
• 英文别名: (S)-5-phenyl-2-(2-naphthyl)-1,3-oxazoline；(5S)-2-naphthalen-2-yl-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 1245618-48-7
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: QYCHGGSWSBPPGQ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-1-(2-naphthoyl)-2-phenylaziridine 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以100%的产率得到(S)-2-(2-naphthyl)-5-phenyl-1,3-oxazoline
  参考文献：
  名称：

  溴三苯基鏻盐促进串联一锅环化成光学活性 2-Aryl-1,3-恶唑啉

  摘要：

  光学活性 2-芳基-1,3-恶唑啉，如芳香碳环、杂环结合的 4-苄基（或苯基）-1,3-恶唑啉及其 5-苄基（或苯基）-1,3-恶唑啉异构体是通过溴三苯基鏻盐成功制备促进氮丙啶环形成和开环顺序过程，包括手性 2-氨基-3-苯基丙醇或 2-氨基-2-苯基乙醇与各种芳族酸在甲苯中在 90°C 和温和的条件下串联一锅环化以优异的产量。这种串联过程的机制也得到了实验证实。

  DOI：

  10.1002/ejoc.201000162

文献信息

• Study on the tandem synthesis of optically active 2-substituted 4 (or 5)-phenyl-1,3-oxazolines
  作者：Haizhen Jiang、Wenjun Lu、Yeshan Cai、Wen Wan、Shaoxiong Wu、Shizheng Zhu、Jian Hao

  DOI：10.1016/j.tet.2012.12.078

  日期：2013.3

  Optically active (S)-2-aryl-4 (or 5)-phenyl-1,3-oxazolines and (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines were synthesized from a tandem one-pot reaction of (S)-2-amino-2-phenylethanol with a corresponding carboxylic acid in toluene at 90 degrees C in the presence of PPh3/CBr4 and excess Et3N. The use of aromatic carboxylic acids were determined to proceed through N-(2-bromo-1-phenyl-ethyl)-arylamides 5 and N-aroyl aziridine intermediates 6, which resulted in the formation of (S)-2-aryl-4-phenyl-1,3-oxazolines and (S)-2-aryl-5-phenyl-1,3-oxazolines, respectively. Concurrently, the reaction with fluorinated aliphatic carboxylic acid substrates proceeded via N-(2-hydroxy-1-phenyl-ethyl)-fluoroalkyl amide intermediates 8, which were converted into N-(2-bromo-1-phenyl-ethyl)-fluoroalkyl amide intermediates 9, and then into (S)-2-fluoroalkyl-4-phenyl-1,3-oxazolines as final products. Reaction mechanisms that mainly passed through the formation of aziridine intermediates 6 in the reaction with aromatic carboxylic acids and the formation of fluoroalkyl amide intermediates 8 and 9 in the reaction with fluorinated aliphatic carboxylic acid were proposed. The acidities of the carboxylic acids that were employed were found to play a key role in the selective formation of various intermediates during this reaction. (c) 2013 Elsevier Ltd. All rights reserved.