ethyl (E)-3-(2-hydroxy-4-methoxyphenyl)acrylate | 139386-27-9

• 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: ethyl (E)-3-(2-hydroxy-4-methoxyphenyl)acrylate
• 英文别名: (E)-ethyl 3-(2-hydroxy-4-methoxyphenyl)acrylate；Ethyl (E)-3-(2-Hydroxy-4-methoxyphenyl)acrylate；ethyl (E)-3-(2-hydroxy-4-methoxyphenyl)prop-2-enoate
• CAS: 139386-27-9
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: XFXBVFUUEWWMFT-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(2-hydroxy-4-methoxyphenyl)acrylate 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-甲氧基香豆素
  参考文献：
  名称：

  通过原位官能化肉桂酸酯的自由基三氟甲基化反应制备 3-三氟甲基化香豆素和喹诺酮

  摘要：

  开发了一种邻羟基肉桂酸酯的三氟甲基化方法，以实现 3-三氟甲基化香豆素的区域选择性合成。该反应采用 Togni 试剂作为 CF3 源，在温和条件下进行，显示出良好的官能团耐受性。这种铜介导的方法的范围进一步扩展到从邻氨基肉桂衍生物开始合成 3-三氟甲基化喹诺酮。有趣的是，进一步开发了从水杨醛开始的 3-三氟甲基化香豆素的连续一锅合成。探索了这种级联反应的机制，发现自由基途径与所得结果一致。

  DOI：

  10.1002/ejoc.201601181
• 作为产物：
  描述：

  7-甲氧基香豆素 在 盐酸 、 氢氧化钾 、 sodium sulfite 作用下， 生成 ethyl (E)-3-(2-hydroxy-4-methoxyphenyl)acrylate
  参考文献：
  名称：

  A simple technique of using novel thread-holding and knot-pushing forceps for extracorporeal knot-tying

  摘要：

  We designed some novel knot-pushing forceps for extracorporeal knot-tying and describe herein our simple technique of utilizing them. These forceps are modified only by a single l-mm hole between their jaws, which hold a thread and push the knot toward the ligating tissue. The application of this simple device was handled well by surgeons beginning to perform advanced endoscopic surgery. The simple modification explained in this report seems applicable to most of the forceps currently used.

  DOI：

  10.1007/s005950070132

文献信息

• A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
  作者：Xiaofeng Ma、Joshua J. Farndon、Tom A. Young、Natalie Fey、John F. Bower

  DOI：10.1002/anie.201708176

  日期：2017.11.13

  A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

  概述了具有广泛范围的 CN 键形成脱芳构化方案。具体来说，双功能氨基试剂用于顺序亲核和亲电CN键形成，后者影响关键的脱芳构化步骤。使用这种方法，只需两到三个步骤即可将 γ-芳基化醇转化为各种差异保护的螺环吡咯烷。
• A convenient synthesis of a simple coumarin.
  作者：Hisashi ISHII、Yasuko KANEKO、Hidetoshi MIYAZAKI、Takashi HARAYAMA

  DOI：10.1248/cpb.39.3100

  日期：——

  Reaction of salicylaldehydes (1) with carbethoxymethylenephosphorane in diethylaniline under reflux gave coumarins (3) in excellent vields. Methoxy substituent at C4 on salicylaldehyde (1) facilitated the formation of coumarin from trans-cinnamate (2), which is first prepared by reaction of 1 with Wittng reagent.

  水杨醛 (1) 与二乙氧基亚甲基正膦在二乙基苯胺中回流反应，得到优异产率的香豆素 (3)。水杨醛 (1) 上 C4 上的甲氧基取代基促进了反式肉桂酸酯 (2) 形成香豆素，该反式肉桂酸酯首先通过 1 与 Wittng 试剂反应制备。
• Photoconversion of o-hydroxycinnamates to coumarins and its application to fluorescence imaging
  作者：Sung-Youl Cho、Young-Kyu Song、Joong-Gon Kim、Se-Young Oh、Chan-Moon Chung

  DOI：10.1016/j.tetlet.2009.06.031

  日期：2009.8

  (E)-o-Hydroxycinnamates were synthesized and their photochemical behavior was investigated in liquid and solid states. It was confirmed by H-1 NMR spectroscopy that the (E)-o-hydroxycinnamates converted into the corresponding coumarins via (Z)-o-hydroxycinnamate intermediates. The photoconversion was greatly accelerated in the presence of p-toluenesulfonic acid. The optical properties of the cinnamates were compared with those of the corresponding coumarins. Fluorescence imaging was successfully accomplished by photoirradiation of PMMA films containing the cinnamates. (C) 2009 Elsevier Ltd. All rights reserved.

  （E）-o-水煤气产物通过合成并研究了它们的光化学行为在液态和固态中。通过¹H核磁共振光谱分析法（H-1 NMR spectroscopy）确认，（E）-o-水煤气产物通过（Z）-o-水煤气中间体转化为相应的对调quaresin。在p-toluenesulfonic acid的存在下，光转变被大大加速。比较了与对应对调quaresin的光学性质。通过光照射聚甲基丙烯酸甲酯薄膜中的甲酰苯，成功实现了荧光成像。 （C）2009 Elsevier Ltd. All rights reserved.
• HDAC8 inhibitors for treating cancer
  申请人：City of Hope

  公开号：US10308596B2

  公开（公告）日：2019-06-04

  Provided herein, inter alia, are compound and methods of treating cancer by inhibiting HDAC8.

  本文特别提供了通过抑制 HDAC8 治疗癌症的化合物和方法。
• A Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Witting Reagent (I): A Synthesis of Methoxy- and Hydroxycoumarins
  作者：Takashi Harayama、Keiko Katsuno、Hiromi Nishioka、Masako Fujii、Yoshitaka Nishita、Hisashi Isii、Yasuko Kaneko

  DOI：10.3987/com-94-s(b)54

  日期：——

  Reaction of methoxy- and hydroxysalicylaldehydes (1) with phosphorane in diethylaniline under reflux gave only coumarins (3) in high yields except for 3-methoxysalicylaldehyde (1b). It was clarified that methoxy group(s) at C-4 and C-6 on 1 facilitated the formation of 3.