2-(3-methoxyphenyl)acetoacetic acid ethyl ester | 869277-92-9

• 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: 2-(3-methoxyphenyl)acetoacetic acid ethyl ester
• 英文别名: ethyl 2-(3-methoxyphenyl)-3-oxobutanoate；Ethyl 2-(3-methoxyphenyl)-3-oxobutanoate
• CAS: 869277-92-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: SFSJZLNBUQNUJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)acetoacetic acid ethyl ester 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 [3-(3-methoxyphenyl)-4-methyl-2-oxochromen-7-yl] N,N-dimethylcarbamate
  参考文献：
  名称：

  Discovery and structure–activity relationship of coumarin derivatives as TNF-α inhibitors

  摘要：

  The discovery and structure-activity relationship of a novel series of coumarin-based TNF-alpha inhibitors is described. Starting from the initial lead la, various derivatives were prepared surrounding the coumarin core structure to optimize the in vitro inhibitory activity of TNF-alpha production by human peripheral blood mononuclear cells (hPBMC), stimulated by bacterial lipopolysaccharide (LPS). Selected compounds also demonstrated in vivo inhibition of TNF-alpha production in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.022
• 作为产物：
  描述：

  3-碘苯甲醚 、 乙酰乙酸乙酯 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以85%的产率得到2-(3-methoxyphenyl)acetoacetic acid ethyl ester
  参考文献：
  名称：

  CuI / L-脯氨酸催化的芳基卤化物与活化的亚甲基化合物的偶联反应。

  摘要：

  [反应：请参见文本]在DMSO中CuI / L-脯氨酸的催化下，在Cs2CO3存在下，在40-50℃下，乙酰乙酸乙酯，苯甲酸乙酯和丙二酸二乙酯的芳基化反应顺利进行，从而提供了2-芳基- 1,3-二羰基化合物，收率高。芳基碘化物和芳基溴化物都与这些反应条件相容。

  DOI：

  10.1021/ol0518838

文献信息

• CuI/<scp>l</scp>-Proline-Catalyzed Coupling Reactions of Aryl Halides with Activated Methylene Compounds
  作者：Xiaoan Xie、Guorong Cai、Dawei Ma

  DOI：10.1021/ol0518838

  日期：2005.10.1

  [reaction: see text] The arylation of ethyl acetoacetate, ethyl benzoyl acetate, and diethyl malonate under the catalysis of CuI/L-proline in DMSO proceeds smoothly at 40-50 degrees C in the presence of Cs2CO3 to provide the 2-aryl-1,3-dicarbonyl compounds in good yields. Both aryl iodides and aryl bromides are compatible with these reaction conditions.

  [反应：请参见文本]在DMSO中CuI / L-脯氨酸的催化下，在Cs2CO3存在下，在40-50℃下，乙酰乙酸乙酯，苯甲酸乙酯和丙二酸二乙酯的芳基化反应顺利进行，从而提供了2-芳基- 1,3-二羰基化合物，收率高。芳基碘化物和芳基溴化物都与这些反应条件相容。
• Discovery and structure–activity relationship of coumarin derivatives as TNF-α inhibitors
  作者：Jie-Fei Cheng、Mi Chen、David Wallace、Sovouthy Tith、Thomas Arrhenius、Hirotaka Kashiwagi、Yoshiyuki Ono、Akira Ishikawa、Haruhiko Sato、Toshiro Kozono、Hediki Sato、Alex M. Nadzan

  DOI：10.1016/j.bmcl.2004.03.022

  日期：2004.5

  The discovery and structure-activity relationship of a novel series of coumarin-based TNF-alpha inhibitors is described. Starting from the initial lead la, various derivatives were prepared surrounding the coumarin core structure to optimize the in vitro inhibitory activity of TNF-alpha production by human peripheral blood mononuclear cells (hPBMC), stimulated by bacterial lipopolysaccharide (LPS). Selected compounds also demonstrated in vivo inhibition of TNF-alpha production in rats. (C) 2004 Elsevier Ltd. All rights reserved.