2-(3-trifluoromethylphenyl)acetoacetic acid ethyl ester | 869277-98-5

• 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-trifluoromethylphenyl)acetoacetic acid ethyl ester
• 英文别名: ethyl 3-oxo-2-(3-(trifluoromethyl)phenyl)butanoate；ethyl 3-oxo-2-[3-(trifluoromethyl)phenyl]butanoate
• CAS: 869277-98-5
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: GPMZGPZKYGAWKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-trifluoromethylphenyl)acetoacetic acid ethyl ester 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 [4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]chromen-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：

  间溴三氟甲苯 、 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 32.0h， 以76%的产率得到2-(3-trifluoromethylphenyl)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

• Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0972770B1

  公开（公告）日：2001-09-19
• Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)
  作者：Jay A. Cadieux、Zaihui Zhang、Maryanne Mattice、Alison Brownlie-Cutts、Jianmin Fu、Laszlo G. Ratkay、Rainbow Kwan、Jay Thompson、Joseph Sanghara、Jing Zhong、Y. Paul Goldberg

  DOI：10.1016/j.bmcl.2011.11.069

  日期：2012.1

  Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5-hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics. (C) 2011 Elsevier Ltd. All rights reserved.
• US6281219B1
  申请人：——

  公开号：US6281219B1

  公开（公告）日：2001-08-28
• [EN] PYRAZOLE AND PYRROLE COMPOUNDS USEFUL IN TREATING IRON DISORDERS<br/>[FR] COMPOSÉS À BASE DE PYRAZOLE ET DE PYRROLE UTILES DANS LE TRAITEMENT DE TROUBLES DU MÉTABOLISME DU FER
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2008121861A2

  公开（公告）日：2008-10-09

  [EN] This invention is directed to pyrazole and pyrrole compounds, for example, compounds of formula (I): wherein R¹, R², R³ and R⁴ are as defined herein, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.
  [FR] L'invention concerne des composés à base de pyrazole et de pyrrole, par exemples des composés de formule (I) où R¹, R², R³ et R⁴ sont tels que définis dans la description, tels que leurs stéréoisomères, énantiomères, tautomères ou leurs mélanges, ou sels pharmaceutiquement acceptables, leurs solvates ou promédicaments, destinés au traitement de troubles du métabolisme du fer. L'invention concerne également des compositions pharmaceutiques renfermant ces composés et des procédés d'utilisation de ces composés pour traiter les troubles du métabolisme du fer.