diethyl 2-hydroxy-2-[1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl]malonate | 110251-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: diethyl 2-hydroxy-2-[1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl]malonate
• 英文别名: hydroxy-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-malonic acid diethyl ester；Hydroxy-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-malonsaeure-diaethylester；diethyl 2-(1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl)-2-hydroxymalonate；diethyl 2-hydroxy-2-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)propanedioate
• CAS: 110251-02-0
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: XCNWXGJSCRNCIL-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C(Solv: ligroine (8032-32-4))
• 沸点：
  182-183 °C(Press: 0.4 Torr)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-hydroxy-2-[1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl]malonate 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 Ethyl 2-(2-ethoxy-2-oxoethyl)-3-oxo-5,6-dihydrobenzo[h]cinnoline-4-carboxylate
  参考文献：
  名称：

  Synthesis, Activity, and Molecular Modeling of a New Series of Tricyclic Pyridazinones as Selective Aldose Reductase Inhibitors

  摘要：

  Three new series of tricyclic pyridazinones have been synthesized and tested in vitro in order to assess (i) their ability to inhibit aldose reductase enzyme (ALR2) and (ii) their specificity toward the target enzyme with respect to other related oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. The inhibitory capability of the most effective compounds (IC50 values ranging from 6.44 to 12.6 mu M) appears to be associated with a rather significant specificity for ALR2. Molecular mechanics and molecular dynamic calculations performed on the ALR2-inhibitor complex give indications of specific interaction sites responsible for the binding, thus providing information for the design of new inhibitors with improved affinity for the enzyme.

  DOI：

  10.1021/jm960124f
• 作为产物：
  描述：

  (3,4-二氢-1-萘氧基)三甲基硅烷 、 酮基丙二酸二乙酯 在 C₄₃H₆₈CuF₆N₂O₉S₂Si₂ 、 六氟异丙醇 作用下， 以 乙醚 、 水 为溶剂， 反应 49.0h， 以14%的产率得到diethyl 2-hydroxy-2-[1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl]malonate
  参考文献：
  名称：

  Enantioselective Mukaiyama-Aldol Reaction between Enol Silanes and Ketomalonate Catalyzed by the Copper(II) Complex of TIPS-Substituted Bis-oxazoline

  摘要：

  The stable complex [(4'S,5'S)-4b/Cu(Tf)(2)/H2O] (5), obtained from TIPS-Box and Copper triflate, catalyzes enantioselectively the Mukaiyama-aldol reactions between two silyl enol ethers (1a,b) and diethyl ketomalonate (2). Yields are very good and the ee of (R)-3b is up to 94%. When the reaction was catalyzed by 4-Ph-Box complex [(4'R)-4a/Cu(Tf)(2)], in which the configuration at the C-4 centre is opposite to that of 5, the same enantiomer was obtained. The undistorted square pyramidal structure of complex 5, determined by crystallographic structure, and the effect of water and molecular sieves on efficiency and selectivity of the catalyst, suggest some proposals to rationalize the resulting stereoselectivity.

  DOI：

  10.3987/com-12-s(n)11

文献信息

• PYRIDAZINE COMPOUNDS AND METHODS
  申请人：Watterson Martin

  公开号：US20090029985A1

  公开（公告）日：2009-01-29

  The invention relates to novel chemical compounds, compositions and methods of making and using the same. In particular, the invention provides pyridazine compounds and/or related heterocyclic derivatives, compositions comprising the same, and methods of using pyridazine compounds and/or related heterocyclic derivatives and compositions comprising the same, for modulation of cellular pathways (e.g., signal transduction pathways), for treatment or prevention of inflammatory diseases (e.g., Alzheimer's disease), for research, drug screening, and therapeutic applications.

  本发明涉及新型化学化合物、组合物及其制备和使用的方法。具体而言，本发明提供了吡嗪化合物和/或相关的杂环衍生物，包括这些化合物的组合物，以及使用吡嗪化合物和/或相关的杂环衍生物和组合物的方法，用于调节细胞通路（例如信号转导通路），用于治疗或预防炎症性疾病（例如阿尔茨海默氏病），用于研究、药物筛选和治疗应用。
• Pyridazine compounds and methods
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US08063047B2

  公开（公告）日：2011-11-22

  The invention relates to novel chemical compounds of Formula I compositions and methods of using the same. In particular, the invention provides pyridazine compounds and/or related heterocyclic derivatives, compositions comprising the same, and methods of using pyridazine compounds and/or related heterocyclic derivatives and compositions comprising the same, for modulation of cellular pathways (e.g., signal transduction pathways), for treatment or prevention of inflammatory diseases (e.g., Alzheimer's disease), for research, drug screening, and therapeutic applications.

  本发明涉及一种新型的化合物I式、其组成和使用方法。特别地，本发明提供了吡嗪化合物和/或相关杂环衍生物、包含它们的组合物，以及使用吡嗪化合物和/或相关杂环衍生物和组合物的方法，用于调节细胞途径（例如，信号转导途径），治疗或预防炎症性疾病（例如，阿尔茨海默病），用于研究、药物筛选和治疗应用。
• Synthesen in der Reihe der Anthelmintika III. Mitteilung
  作者：Karl W. Rosenmund、Joachim Gutschmidt

  DOI：10.1002/ardp.19552880103

  日期：——
• WO2006/50359
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1812007A4
  申请人：——

  公开号：EP1812007A4

  公开（公告）日：2009-04-01