ethyl (E)-3-(4-(diethylamino)phenyl)acrylate | 119516-32-4

• 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: ethyl (E)-3-(4-(diethylamino)phenyl)acrylate
• 英文别名: Ethyl (2E)-3-[4-(diethylamino)phenyl]prop-2-enoate；ethyl (E)-3-[4-(diethylamino)phenyl]prop-2-enoate
• CAS: 119516-32-4
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: ASLBXRNVTSCIJY-FMIVXFBMSA-N

物化性质

• 沸点：
  160 °C(Press: 0.45 Torr)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(4-(diethylamino)phenyl)acrylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以0.4 g的产率得到trans-4-diethylaminocinnamyl alcohol
  参考文献：
  名称：

  Chao, Herbert S.-I., Synthetic Communications, 1988, vol. 18, # 14, p. 1641 - 1650

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸乙酯 、 N,N-二乙基-4-氨基苯甲醛 在 sodium 作用下， 以10%的产率得到ethyl (E)-3-(4-(diethylamino)phenyl)acrylate
  参考文献：
  名称：

  Chao, Herbert S.-I., Synthetic Communications, 1988, vol. 18, # 14, p. 1641 - 1650

  摘要：

  DOI：

文献信息

• Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C–H Annulation and Their Application to Pd-Catalyzed Aerobic C–H Alkenylation
  作者：Hyun Tae Kim、Eunsu Kang、Minkyu Kim、Jung Min Joo

  DOI：10.1021/acs.orglett.1c01040

  日期：2021.5.7

  A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C–H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C–H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary

  通过涉及Rh催化的C–H环化反应的模块化方法，制备了一类新的双齿配体。最终形成的构象受约束的配体使Pd催化的C-H链烯基在富电子和富电子芳烃的位置上受阻较小，同时促进了Pd（0）中间体容易被氧氧化。这种新引入的配体类别与为Pd催化的氧化反应开发的配体互补，并可能在过渡金属催化的反应中找到广泛的应用。
• <i>para</i>-Selective C–H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis
  作者：Kananat Naksomboon、Jordi Poater、F. Matthias Bickelhaupt、M. Ángeles Fernández-Ibáñez

  DOI：10.1021/jacs.9b01908

  日期：2019.4.24

  Herein we report a highly para-selective C–H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity

  在此，我们报道了通过 Pd/S,O-配体基催化剂对苯胺衍生物进行高度对位选择性 C-H 烯化。该反应在温和的反应条件下进行，反应效率高，底物范围广，包括单、二和三取代的叔、仲和伯苯胺。S,O-配体导致底物范围的显着改善和观察到的高对位选择性。该方法操作简单、可扩展，并且可以在有氧条件下进行。
• Green synthesis of ethyl cinnamates under microwave irradiation: photophysical properties, cytotoxicity, and cell bioimaging
  作者：Miguel Angel Aztatzi-Mendoza、Edgar Leonel Porras-Núñez、Verónica M. Rivas-Galindo、Pilar Carranza-Rosales、Irma Edith Carranza-Torres、Catalina García-Vielma、Iran F. Hernández Ahuactzi、Susana López-Cortina、Israel López、Eugenio Hernández-Fernández

  DOI：10.1039/d3ra06443c

  日期：——

  A simple and green method for the synthesis of six ethyl cinnamates was performed via Horner–Wadsworth–Emmons reaction under microwave irradiation. The photoluminescent properties of all compounds in ethyl acetate solutions were evaluated demonstrating that all compounds exhibit fluorescence. Five compounds exhibited blue emissions in the 369–442 nm range, and another compound exhibited blue-green

  通过微波辐射下的 Horner-Wadsworth-Emmons 反应，进行了一种简单、绿色的合成六种肉桂酸乙酯的方法。评估了乙酸乙酯溶液中所有化合物的光致发光性质，证明所有化合物均表现出荧光。五种化合物在 369-442 nm 范围内呈现蓝色发射，另一种化合物在 504 nm 范围内呈现蓝绿色发射。最后一种化合物显示出最大的斯托克斯位移（134 nm）和最高的量子产率（17.8%）。两种化合物的消光系数值 ( ε ) 高于 30 000 M -1 cm -1 ，适合细胞生物成像应用。从这个意义上说，使用不同浓度的 Vero 细胞进行细胞毒性测定；结果表明，这些化合物在最高测试浓度（20 μg mL -1 ）下没有细胞毒性。最后，通过荧光显微镜进行的定位分析和使用 Vero 细胞的细胞染色表明，这些化合物以选择性方式对细胞质和细胞核进行染色。
• 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。
• Synthesis of Monocarbenepalladium(0) Complexes and Their Catalytic Behavior in Cross-Coupling Reactions of Aryldiazonium Salts
  作者：Kumaravel Selvakumar、Alexander Zapf、Anke Spannenberg、Matthias Beller

  DOI：10.1002/1521-3765(20020902)8:17<3901::aid-chem3901>3.0.co;2-e

  日期：2002.9.2

  The first monocarbenepalladium(0) complexes with benzoquinone and naphthoquinone as additional ligands have been prepared. As demonstrated by NMR spectroscopy and X-ray analysis, the complexes show a unique coordination mode giving quinone-bridged dimers. The monocarbenepalladium(0) complexes allow efficient cross-coupling reactions of aryldiazonium salts with olefins (Heck reaction) and arylboronic acids (Suzuki reaction).