2-Hydroxy-zimtsaeure-anilid | 86774-84-7

• 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: 2-Hydroxy-zimtsaeure-anilid
• 英文别名: (E)-3-(2-hydroxyphenyl)-N-phenylprop-2-enamide
• CAS: 86774-84-7
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: LKXPYLJFPPGVIW-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2R,2aR,8bR)-1-(2-hydroxyphenyl)-3-oxo-N-phenyl-1,2,2a,8b-tetrahydrocyclobuta[c]chromene-2-carboxamide 以45%的产率得到
  参考文献：
  名称：

  YONEZAWA, NORIYUKI;YOSHIDA, TSUYOSHI;HASEGAWA, MASAKI, J. CHEM. SOC. PERKIN TRANS., 1983, N 5, 1083-1086

  摘要：

  DOI：

文献信息

• Late‐Stage Direct <i>o</i> ‐Alkenylation of Phenols by Pd ^II ‐Catalyzed C−H Functionalization
  作者：Yandong Dou、Kenry、Jiang Liu、Jianze Jiang、Qing Zhu

  DOI：10.1002/chem.201900530

  日期：2019.5.17

  phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C−H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under

  通过Pd II催化的直接C-H官能化已开发出未保护的酚的o-烯基化。这项工作以酚基团为导向基团，并实现了酚的位点选择性C-H键官能化，从而在60°C时以中等至极好的收率获得了相应的产品。该反应的优点包括使用苯酚作为指导基团进行前所未有的CH官能化，区域选择性高，底物范围广，反应条件温和且效率高。据我们所知，这是利用酚羟基作为指导基团对未保护的酚进行区域选择性CH烯基化的第一个例子。未保护的酪氨酸的烯基化和分子内环化也可以在该催化体系下以高收率成功进行。此外，
• 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。
• Yonezawa, Noriyuki; Yoshida, Tsuyoshi; Hasegawa, Masaki, Journal of the Chemical Society. Perkin transactions I, 1983, # 5, p. 1083 - 1086
  作者：Yonezawa, Noriyuki、Yoshida, Tsuyoshi、Hasegawa, Masaki

  DOI：——

  日期：——
• YONEZAWA, NORIYUKI;YOSHIDA, TSUYOSHI;HASEGAWA, MASAKI, J. CHEM. SOC. PERKIN TRANS., 1983, N 5, 1083-1086
  作者：YONEZAWA, NORIYUKI、YOSHIDA, TSUYOSHI、HASEGAWA, MASAKI

  DOI：——

  日期：——