N-(p-benzyloxycinnamoyl)-(S)-phenylalaninol | 1557101-69-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(p-benzyloxycinnamoyl)-(S)-phenylalaninol
• 英文别名: (E)-N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-3-(4-phenylmethoxyphenyl)prop-2-enamide
• CAS: 1557101-69-5
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: LDMJURGGNFWBBC-IGVGMEOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-benzyloxycinnamoyl)-(S)-phenylalaninol 在 氯化亚砜 、 potassium carbonate 、 sodium bromide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以64%的产率得到(4S)-4-benzyl-2-(p-benzyloxycinnamoyl)-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
• 作为产物：
  描述：

  L-苯丙氨醇 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 N-(p-benzyloxycinnamoyl)-(S)-phenylalaninol
  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.