N-propyl-2-hydroxycinnamamide | 190366-77-9

• 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-propyl-2-hydroxycinnamamide
• 英文别名: (E)-3-(2-hydroxyphenyl)-N-propylprop-2-enamide
• CAS: 190366-77-9
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: TYMWCTLTQCWPQF-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-propyl-2-hydroxycinnamamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.0h， 生成 2-<(Z)-3-(propylamino)-3-oxo-1-propenyl>phenyl acetate
  参考文献：
  名称：

  Two new improved approaches to the synthesis of coumarin-based prodrugs

  摘要：

  Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated me clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of me cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00121-0
• 作为产物：
  描述：

  正丙胺 、 反式-2-羟基肉桂酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到N-propyl-2-hydroxycinnamamide
  参考文献：
  名称：

  A Photo-Sensitive Protecting Group for Amines Based on Coumarin Chemistry.

  摘要：

  我们一直需要开发新的胺保护基团，这种保护基团可以在温和的条件下裂解，而且与现有的保护基团有本质区别。在本文中，我们报告了使用邻羟基反式肉桂酸作为胺的光敏保护基团的研究。该设计利用了邻羟基-顺式肉桂酸及其衍生物的反式-顺式光异构化和随之而来的简易内酯化。我们发现，对于具有不同结构特征的各种胺，保护和脱保护反应都能以高产率进行。脱保护反应使用低强度紫外光（365 纳米），这与其他常用氨基保护基团的脱保护条件有本质区别。因此，该方法是对其他现有方法的补充，可以对复杂有机分子中的不同官能团进行选择性操作。

  DOI：

  10.1248/cpb.45.715

文献信息

• A Photo-Sensitive Protecting Group for Amines Based on Coumarin Chemistry.
  作者：Binghe WANG、Ailian ZHENG

  DOI：10.1248/cpb.45.715

  日期：——

  There is a continuing need for the development of new protecting groups for amines which can be cleaved under conditions that are mild and fundamentally different from what are already available. In this paper, we report our studies in using o-hydroxy-trans-cinnamic acid as a photo-sensitive protecting group for amines. The design takes advantage of the trans-cis photo-isomerization and the ensuing facile lactonization of o-hydroxy-cis-cinnamic acid and derivatives. We have found that both the protection and deprotection can be carried out in high yields for a variety of amines with different structural features. The deprotection reaction uses low intensity UV light (365 nm), which is fundamentally different from the conditions used for the deprotection of other commonly used amino-protecting groups. Therefore, the method complements other available methods in allowing for selective manipulation of different functional groups in a complex organic molecule.

  我们一直需要开发新的胺保护基团，这种保护基团可以在温和的条件下裂解，而且与现有的保护基团有本质区别。在本文中，我们报告了使用邻羟基反式肉桂酸作为胺的光敏保护基团的研究。该设计利用了邻羟基-顺式肉桂酸及其衍生物的反式-顺式光异构化和随之而来的简易内酯化。我们发现，对于具有不同结构特征的各种胺，保护和脱保护反应都能以高产率进行。脱保护反应使用低强度紫外光（365 纳米），这与其他常用氨基保护基团的脱保护条件有本质区别。因此，该方法是对其他现有方法的补充，可以对复杂有机分子中的不同官能团进行选择性操作。
• Two new improved approaches to the synthesis of coumarin-based prodrugs
  作者：Ailian Zheng、Wei Wang、Huijuan Zhang、Binghe Wang

  DOI：10.1016/s0040-4020(99)00121-0

  日期：1999.4

  Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated me clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of me cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.