(E)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester | 911365-92-9

• 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: (E)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester
• 英文别名: ethyl E-3-(4-diethylamino-2-hydroxy-phenyl)propenoate；(E)-ethyl 3-(4-(N,N-diethylamino)-2-hydroxyphenyl)acrylate
• CAS: 911365-92-9
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: JSAKYNFAODCYDS-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester 在 Tris buffer 作用下， 以 乙腈 为溶剂， 生成 (Z)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  带有荧光报告的双光子解笼锁：theo-Hydroxycinnamic 平台的评估

  摘要：

  本文评估了 o-羟基肉桂酸平台，用于设计具有单光子和双光子激发荧光报告的高效笼罩基团。通过偶联商业或现成的合成子，模型肉桂酸酯很容易一步制备。它们表现出大的单光子吸收，可以在近紫外范围内进行调整。通过 1 H NMR、UV-vis 吸收和稳态荧光发射研究单光子激发后的解笼锁。在整个研究系列中，笼底物在光解时定量释放。同时，uncaging 会释放强荧光副产物，可用作定量底物递送的报告基因。单光子吸收后导致解笼锁的双键光异构化的量子产率大多在 10% 范围内。利用解笼锁副产物有利的光物理特性，我们使用一系列基于荧光发射的技术来测量本肉桂酸酯的双光子激发的解笼锁横截面。在 750 nm 处显示 1-10 GM 范围内的值，它们与迄今为止报道的最有效的笼养组相比令人满意。值得注意的是，正如在活斑马鱼胚胎中观察到的结果所暗示的那样，双光子激发的解笼锁行为在体内得以保留。从目前收集到的数据的分析中提

  DOI：

  10.1021/ja0722022
• 作为产物：
  描述：

  (Z)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester 在 Tris buffer 作用下， 以 乙腈 为溶剂， 生成 (E)-3-(4-diethylamino-2-hydroxyphenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  带有荧光报告的双光子解笼锁：theo-Hydroxycinnamic 平台的评估

  摘要：

  本文评估了 o-羟基肉桂酸平台，用于设计具有单光子和双光子激发荧光报告的高效笼罩基团。通过偶联商业或现成的合成子，模型肉桂酸酯很容易一步制备。它们表现出大的单光子吸收，可以在近紫外范围内进行调整。通过 1 H NMR、UV-vis 吸收和稳态荧光发射研究单光子激发后的解笼锁。在整个研究系列中，笼底物在光解时定量释放。同时，uncaging 会释放强荧光副产物，可用作定量底物递送的报告基因。单光子吸收后导致解笼锁的双键光异构化的量子产率大多在 10% 范围内。利用解笼锁副产物有利的光物理特性，我们使用一系列基于荧光发射的技术来测量本肉桂酸酯的双光子激发的解笼锁横截面。在 750 nm 处显示 1-10 GM 范围内的值，它们与迄今为止报道的最有效的笼养组相比令人满意。值得注意的是，正如在活斑马鱼胚胎中观察到的结果所暗示的那样，双光子激发的解笼锁行为在体内得以保留。从目前收集到的数据的分析中提

  DOI：

  10.1021/ja0722022

文献信息

• 3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of<i>ortho</i>-Functionalized Cinnamic Esters
  作者：Slim Chaabouni、Florent Simonet、Alison François、Souhir Abid、Chantal Galaup、Stefan Chassaing

  DOI：10.1002/ejoc.201601181

  日期：2017.1.10

  regioselective synthesis of 3-trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF3 source under mild conditions and showed good functional- group tolerance. The scope of this copper-mediated method was further expanded to the synthesis of 3-trifluoromethylated carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot synthesis of

  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。
• Visible and NIR light photoactivatable <i>o</i>-hydroxycinnamate system for efficient drug release with fluorescence monitoring
  作者：Ajay Gupta、Neelu Singh、Aryan Gautam、Neetesh Dhakar、Sunil Kumar、Pijus K. Sasmal

  DOI：10.1039/d2md00438k

  日期：——

  molecules in the biomedical field. However, designing PPGs that can be efficiently activated by biologically benign visible and NIR light with fluorescence monitoring is still a great challenge. Herein, we report o-hydroxycinnamate-based PPGs that can be activated by both visible (one-photon) and NIR (two-photon) light for controlled drug release with real-time monitoring. Thus, a photoremovable 7-diethylamino

  光活化保护基团（PPG）已成为控制生物医学领域重要生物学分子活性的强大材料。然而，设计可通过生物良性可见光和近红外光以及荧光监测有效激活的 PPG 仍然是一个巨大的挑战。在此，我们报道了基于邻羟基肉桂酸酯的 PPG，它可以被可见光（单光子）和近红外光（双光子）激活，通过实时监测控制药物释放。因此，可光去除的7-二乙氨基邻羟基肉桂酸酯基团共价连接至抗癌药物吉西他滨，以建立可光活化的前药系统。在可见光（400-700 nm）或近红外（800 nm）光激发下，前药有效释放药物，通过监测强荧光香豆素报告基因的形成来定量药物。通过 FACS 和荧光显微镜成像确定，前药被癌细胞吸收，并有趣地在线粒体内积聚。此外，该前药在可见光和近红外光照射下表现出光触发、剂量依赖性和时间控制的细胞死亡。这种光激活系统在未来可能有用并适用于生物医学先进疗法的开发。
• FLUORESCENT ENZYME SUBSTRATES AND METHOD FOR ASSAYING ENZYMATIC ACTIVITY
  申请人：Laboratory of Molecular Biophotonics

  公开号：EP0892067A1

  公开（公告）日：1999-01-20

  The enzyme substrate according to this invention has within its molecule both a group to be cleaved by an enzyme reaction and a group that forms a strongly fluorescent coumarin derivative through intramolecular lactonization when cleaved by the enzyme reaction. Furthermore, the method for determining an enzyme activity according to this invention comprises conducting the enzyme reaction by the use of the enzyme substrate of the invention and determining the enzyme activity by means of the measurement of fluorescence of the coumarin derivative formed.

  根据本发明的酶底物在其分子内既有一个将被酶反应裂解的基团，又有一个在被酶反应裂解时通过分子内内酯化形成强荧光香豆素衍生物的基团。此外，根据本发明确定酶活性的方法包括使用本发明的酶底物进行酶反应，并通过测量所形成的香豆素衍生物的荧光来确定酶活性。
• Visible Light Excitation of CdSe Nanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands
  作者：Maikel Wijtmans、Sandra J. Rosenthal、Binne Zwanenburg、Ned A. Porter

  DOI：10.1021/ja063562c

  日期：2006.9.1

  The photochemical properties of organic ligands on the surface of nanocrystalline CdSe particles were examined. A number of thiols carrying a substituted cinnamate tail was synthesized. In solution, these cinnamate compounds undergo light-induced ( 374 nm) E-Z isomerization, followed by a nonphotolytic lactonization to give highly fluorescent coumarin. The cinnamate-thiols were successfully exchanged onto the CdSe nanocrystal, and the photochemical behavior of these conjugates was studied. Upon aerobic photolysis at 374 nm, the surface cinnamates released coumarin accompanied by rapid nanocrystal degradation. This degradation was not observed under similar anaerobic conditions or when the organic ligands did not contain the cinnamate group. Surprisingly, very similar results were obtained upon irradiation at visible wavelengths at which the cinnamate has no absorption. With the aid of UV-visible absorption spectroscopy, fluorescence spectroscopy, and electrochemistry, a unified theory for both the increased photoinstability of the nanocrystal as well as the coumarin release was proposed. It involves cinnamate radical anions on the CdSe surface, formed upon electron transfer from the excited nanocrystal to the surface cinnamate, undergoing E-Z isomerization. Practically, this results in the remarkable ability to release coumarin from nanocrystal ligands simply by exciting the nanocrystal with visible light. This new photorelease protocol not only aids in the understanding of fundamental nanocrystal-ligand interactions but may also offer new opportunities in the areas of drug delivery and imaging.
• US6207365B1
  申请人：——

  公开号：US6207365B1

  公开（公告）日：2001-03-27