4-ethyl-2-vinylaniline | 1395060-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-ethyl-2-vinylaniline
• 英文别名: 2-Ethenyl-4-ethylaniline；2-ethenyl-4-ethylaniline
• CAS: 1395060-14-6
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: UYKYANRXZIAZRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-ethyl-2-vinylaniline 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 四(三苯基膦)钯 、 (氯亚甲基)二甲基氯化铵 、 potassium acetate 、 sodium acetate 、 palladium diacetate 、 三溴化硼 、 sodium hydride 、 三苯基膦 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 4-(2-Ethyl-5-methyl-11-methylidene-6-oxobenzo[c][1]benzazepin-8-yl)benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Transrepression-Selective Liver X Receptor (LXR) Ligands with 5,11-Dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one Skeleton

  摘要：

  To obtain novel transrepression-selective liver X receptor (LXR) ligands, we adopted a strategy of reducing the transactivational agonistic activity of the 5,11-dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one derivative 10, which exhibits LXR-mediated transrepressional and transactivational activity. Structural modification of 10 based on the reported X-ray crystal structure of the LXR ligand-binding domain led to a series of compounds, of which almost all exhibited transrepressional activity at 1 or 10 mu M but showed no transactivational activity even at 30 mu M. Among the compounds obtained, 18 and 22 were confirmed to have LXR-dependent transrepressional activity by using peritoneal macrophages from wild-type and LXR-null mice. A newly developed fluorescence polarization assay indicated that they bind directly to LXR alpha. Next, further structural modification was performed with the guidance of docking simulations with LXR alpha, focusing on enhancing the binding of the ligands with LXR alpha through the introduction of substituents or heteroatom(s). Among the compounds synthesized, compound 48, bearing a hydroxyl group, showed potent, selective, and dose-dependent transrepressional activity.

  DOI：

  10.1021/jm3002394
• 作为产物：
  描述：

  4-乙基苯胺 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 氢溴酸 、 caesium carbonate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 4-ethyl-2-vinylaniline
  参考文献：
  名称：

  2-乙烯基苯胺和炔烃通过 C≡C 三键裂解和双氧活化直接合成色氨酸

  摘要：

  已经开发出一种意想不到的无金属 C≡C 三键断裂、双氧活化和重新组装成色氨酸衍生物。这种化学反应提供了一种新颖、简单且有效的方法，可以在温和条件下从简单底物获得高价值的色氨酸衍生物。机理研究可能会通过 CC 键裂解和分子氧活化促进新方法的发现。

  DOI：

  10.1021/jacs.6b08094

文献信息

• 一种色醇及色胺类衍生物的合成方法
  申请人：北京大学

  公开号：CN106831533A

  公开（公告）日：2017-06-13

  本发明公开了一种色醇及色胺类衍生物的合成方法，所述方法包括将具有通式(I)的2‑乙烯基苯胺类化合物与具有通式(II)的炔烃类化合物在有机溶剂中混合，反应制得所述通式(III)的色醇及色胺类衍生物。采用本发明的方法，能够廉价高效地合成色醇及色胺类衍生物，在实际生产中将具有广泛的应用前景。
• Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C≡C Triple Bond Cleavage and Dioxygen Activation
  作者：Tao Shen、Yiqun Zhang、Yu-Feng Liang、Ning Jiao

  DOI：10.1021/jacs.6b08094

  日期：2016.10.12

  metal-free C≡C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.

  已经开发出一种意想不到的无金属 C≡C 三键断裂、双氧活化和重新组装成色氨酸衍生物。这种化学反应提供了一种新颖、简单且有效的方法，可以在温和条件下从简单底物获得高价值的色氨酸衍生物。机理研究可能会通过 CC 键裂解和分子氧活化促进新方法的发现。
• Design, Synthesis, and Biological Evaluation of Novel Transrepression-Selective Liver X Receptor (LXR) Ligands with 5,11-Dihydro-5-methyl-11-methylene-6<i>H</i>-dibenz[<i>b</i>,<i>e</i>]azepin-6-one Skeleton
  作者：Atsushi Aoyama、Kaori Endo-Umeda、Kenji Kishida、Kenji Ohgane、Tomomi Noguchi-Yachide、Hiroshi Aoyama、Minoru Ishikawa、Hiroyuki Miyachi、Makoto Makishima、Yuichi Hashimoto

  DOI：10.1021/jm3002394

  日期：2012.9.13

  To obtain novel transrepression-selective liver X receptor (LXR) ligands, we adopted a strategy of reducing the transactivational agonistic activity of the 5,11-dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one derivative 10, which exhibits LXR-mediated transrepressional and transactivational activity. Structural modification of 10 based on the reported X-ray crystal structure of the LXR ligand-binding domain led to a series of compounds, of which almost all exhibited transrepressional activity at 1 or 10 mu M but showed no transactivational activity even at 30 mu M. Among the compounds obtained, 18 and 22 were confirmed to have LXR-dependent transrepressional activity by using peritoneal macrophages from wild-type and LXR-null mice. A newly developed fluorescence polarization assay indicated that they bind directly to LXR alpha. Next, further structural modification was performed with the guidance of docking simulations with LXR alpha, focusing on enhancing the binding of the ligands with LXR alpha through the introduction of substituents or heteroatom(s). Among the compounds synthesized, compound 48, bearing a hydroxyl group, showed potent, selective, and dose-dependent transrepressional activity.