4-(4-trifluoromethylbenzyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester

• 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-(4-trifluoromethylbenzyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-phenyl-4-[[4-(trifluoromethyl)phenyl]methyl]-5H-1,3-oxazole-4-carboxylate
• 化学式: C₂₂H₂₂F₃NO₃
• 分子量: 405.417
• InChiKey: WQESLDCRJXDKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲亚胺酸乙酯盐酸盐 在 氢氧化钾 、 四丁基溴化铵 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 4-(4-trifluoromethylbenzyl)-2-phenyl-1,3-oxazoline-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate

  摘要：

  Practical synthesis of (+/-)-alpha-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The alpha-alkylation and beta-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives alpha-alkylation (up to >99%), and t-BuOK in DMF gives beta-elimination (98%). (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.03.041

文献信息

• An unusual base-dependent α-alkylation and β-elimination of tert-butyl 2-phenyl-2-oxazoline-4-carboxylate: practical synthesis of (±)-α-alkylserines and tert-butyl benzamidoacrylate
  作者：Hyeung-geun Park、Jihye Lee、Myoung Joo Kang、Yeon-Ju Lee、Byeong-Seon Jeong、Jeong-Hee Lee、Mi-Sook Yoo、Mi-Jeong Kim、Sea-hoon Choi、Sang-sup Jew

  DOI：10.1016/j.tet.2004.03.041

  日期：2004.5

  Practical synthesis of (+/-)-alpha-alkylserines and tert-butyl benzamidoacrylate from tert-butyl 2-phenyl-2-oxazoline-4-carboxylate (6) were developed. The alpha-alkylation and beta-elimination of 6 are dramatically dependent upon base conditions. The phase-transfer catalytic condition bearing solid KOH in toluene gives alpha-alkylation (up to >99%), and t-BuOK in DMF gives beta-elimination (98%). (C) 2004 Published by Elsevier Ltd.