(4S)-4-benzyl-2-(p-bromocinnamoyl)-2-oxazoline | 1557101-25-3

• 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: (4S)-4-benzyl-2-(p-bromocinnamoyl)-2-oxazoline
• 英文别名: (4S)-4-benzyl-2-[(E)-2-(4-bromophenyl)ethenyl]-4,5-dihydro-1,3-oxazole
• CAS: 1557101-25-3
• 化学式: C₁₈H₁₆BrNO
• 分子量: 342.235
• InChiKey: ROAVEZAGROMSHD-YRYLYKBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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)-2-(2-diethoxyphosphoryl)acetamide-3-phenylpropanol 在 氯化亚砜 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium bromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.5h， 生成 (4S)-4-benzyl-2-(p-bromocinnamoyl)-2-oxazoline
  参考文献：
  名称：

  Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides

  摘要：

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.003

文献信息

• Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides
  作者：Francisco G. Avalos-Alanís、Eugenio Hernández-Fernández、Rocio Hernández-Romero、Susana López-Cortina、Mario Ordóñez、Oscar García-Barradas、Selene Lagunas-Rivera

  DOI：10.1016/j.tetasy.2013.12.003

  日期：2014.1

  Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a-h in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of beta-phosphonoamide 3 bearing L-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a-h. Additionally, the cyclodehydration of p-phosphonoamide (S)-3 followed by the Horner-Wadsworth-Emmons reaction of p-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a-h. (C) 2013 Elsevier Ltd. All rights reserved.