N-hexyl-3-(4-hydroxy-3-methoxyphenyl)propanamide | 1179525-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-hexyl-3-(4-hydroxy-3-methoxyphenyl)propanamide
• 英文别名: hydroferuloylhexylamide；4-hydroxy-3-methoxyhydrocinnamic acid hexylamide
• CAS: 1179525-30-4
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: DYLMEFZLWLQJMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正己胺 、 S-pentafluorophenyl 3-(4-hydroxy-3-methoxyphenyl)propanethioate 以 氯仿 为溶剂， 反应 0.17h， 以68%的产率得到N-hexyl-3-(4-hydroxy-3-methoxyphenyl)propanamide
  参考文献：
  名称：

  Activation of hydrocinnamic acids with pentafluorophenol versus pentafluorothiophenol: Reactivity towards hexylamine

  摘要：

  In this work we describe and compare the synthesis of four new hexylamides of hydrocinnamic acids, namely hexylamide of hydrocinnamic, 3,4-dimethoxyhydrocinnamic, 4-hydroxy-3-methoxyhydrocinnamic and 3,4-dihydroxyhydrocinnamic acids via pentafluorophenyl esters (PFPEs) versus pentafluorophenyl thioesters (PFPTs) intermediates. It was found that the PRE are the best intermediates for this kind of synthesis giving reactions with less by products, easier work-up, higher overall yields and with the best reactivity towards hexylamine. The X-ray structures of two PRE are also reported. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.09.013

文献信息

• Activation of hydrocinnamic acids with pentafluorophenol versus pentafluorothiophenol: Reactivity towards hexylamine
  作者：Fernanda M.F. Roleira、Fernanda Borges、Lourdes C.R. Andrade、José A. Paixão、Maria J.M. Almeida、Rui A. Carvalho、Elisiário J. Tavares da Silva

  DOI：10.1016/j.jfluchem.2008.09.013

  日期：2009.2

  In this work we describe and compare the synthesis of four new hexylamides of hydrocinnamic acids, namely hexylamide of hydrocinnamic, 3,4-dimethoxyhydrocinnamic, 4-hydroxy-3-methoxyhydrocinnamic and 3,4-dihydroxyhydrocinnamic acids via pentafluorophenyl esters (PFPEs) versus pentafluorophenyl thioesters (PFPTs) intermediates. It was found that the PRE are the best intermediates for this kind of synthesis giving reactions with less by products, easier work-up, higher overall yields and with the best reactivity towards hexylamine. The X-ray structures of two PRE are also reported. (C) 2008 Elsevier B.V. All rights reserved.