N,N-diethyl-3-(2-hydroxyphenyl)-trans-2-propenamide | 92040-79-4

• 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,N-diethyl-3-(2-hydroxyphenyl)-trans-2-propenamide
• 英文别名: trans-N,N-diethyl-o-hydroxycinnamamide；2-hydroxy-trans-cinnamic acid diethylamide；2-Hydroxy-trans-zimtsaeure-diaethylamid；(2E)-N,N-diethyl-3-(2-hydroxyphenyl)prop-2-enamide；(E)-N,N-diethyl-3-(2-hydroxyphenyl)prop-2-enamide
• CAS: 92040-79-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: BGUVUPQHCJEUST-MDZDMXLPSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  409.9±28.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3-(2-hydroxyphenyl)-trans-2-propenamide 以 乙腈 为溶剂， 反应 1.0h， 以68%的产率得到香豆素
  参考文献：
  名称：

  光环化反应。第8部分†。通过光反应反式顺式异构化合成2-喹诺酮，喹啉和香豆素衍生物

  摘要：

  通过traans-o-氨基肉桂酰基衍生物trans - 1和trans-的光环化反应合成了2-喹诺酮2，喹啉3，香豆素（2 H -1-苯并吡喃-2-酮）5和2 H -1-苯并吡喃半缩醛6。ø -hydroxycinnamoyl衍生物反式- 4。反应通过反式-顺式异构化进行，然后进行分子内环化。

  DOI：

  10.1002/jhet.5570390108
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 氯化亚砜 作用下， 生成 N,N-diethyl-3-(2-hydroxyphenyl)-trans-2-propenamide
  参考文献：
  名称：

  The Analgesic Activity of N,N-Dialkyl Amides¹

  摘要：

  DOI：

  10.1021/ja01165a016

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。
• BASE GENERATOR, PHOTOSENSITIVE RESIN COMPOSITION, PATTERN FORMING MATERIAL COMPRISING THE PHOTOSENSITIVE RESIN COMPOSITION, AND PATTERN FORMING METHOD AND ARTICLE USING THE PHOTOSENSITIVE RESIN COMPOSITION
  申请人：Katayama Mami

  公开号：US20110086311A1

  公开（公告）日：2011-04-14

  A photosensitive resin composition which is excellent in resolution, low in cost, and usable in a wide range of structures of polymer precursors each of which is reacted into a final product by a basic substance or by heating in the presence of a basic substance. The photosensitive resin composition includes a base generator which has a specific structure and generates a base by exposure to electromagnetic radiation and heating, and a polymer precursor which is reacted into a final product by the base generator and by a basic substance or by heating in the presence of a basic substance.

  一种光敏树脂组合物，具有分辨率优良、成本低廉和可用于一系列聚合物前体结构的特点，其中每种聚合物前体都可以通过碱性物质或在碱性物质的存在下加热反应成为最终产物。该光敏树脂组合物包括一种具有特定结构并通过电磁辐射和加热产生碱性物质的基发生剂，以及一种聚合物前体，该聚合物前体通过基发生剂和碱性物质或在碱性物质的存在下加热反应成为最终产物。
• 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.
• PHOTOSENSITIVE RESIN COMPOSITION, PATTERN FORMING MATERIAL COMPRISING THE PHOTOSENSITIVE RESIN COMPOSITION, AND PATTERN FORMING METHOD AND ARTICLE USING THE PHOTOSENSITIVE RESIN COMPOSITION
  申请人：DAI NIPPON PRINTING CO., LTD.

  公开号：US20130309607A1

  公开（公告）日：2013-11-21

  A photosensitive resin composition which is excellent in resolution, low in cost, and usable in a wide range of structures of polymer precursors each of which is reacted into a final product by a basic substance or by heating in the presence of a basic substance. The photosensitive resin composition includes a base generator which has a specific structure and generates a base by exposure to electromagnetic radiation and heating, and a polymer precursor which is reacted into a final product by the base generator and by a basic substance or by heating in the presence of a basic substance.
• US8476444B2
  申请人：——

  公开号：US8476444B2

  公开（公告）日：2013-07-02