ethyl 6-hydroxy-3-oxohexanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 6-hydroxy-3-oxohexanoate
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: YHHUQIKUBPZAEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-hydroxy-3-oxohexanoate 在 哌啶 、 4-甲基苯磺酸吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 6,7-dimethoxy-2-(3-tetrahydropyranyloxypropyl) quinoline-3-carboxylic acid
  参考文献：
  名称：

  New developments in redox chemical delivery systems by means of 1,4-dihydroquinoline-based targetor: Application to galantamine delivery to the brain

  摘要：

  The therapeutic efficiency of palliative treatments of AD, mostly based on acetylcholinesterase (AChE) inhibitors, is marred by serious adverse effects due to peripheral activity of these AChE inhibitors. In the literature, a redox-based chemical delivery system (CDS) has been developed to enhance drugs distribution to the brain while reducing peripheral side effects. Herein, we disclose two new synthetic strategies for the preparation of 1,4-dihydroquinoline/quinolinium salt redox-based systems particularly well designed for brain delivery of drugs sensitive to alkylation reactions. These strategies have been applied in the present case to the AChE inhibitor galantamine with the aim of alleviating adverse effects observed with cholinergic AD treatment. The first strategy is based on an intramolecular alkylation reaction as key step, whilst the second strategy relies on a useful coupling between galantamine and quinolinium salt key intermediate. In the course of this work, polymer-supported reagents and a solid-phase synthesis approach revealed to be highly helpful to develop this redox-based galantamine CDS. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.022
• 作为产物：
  描述：

  γ-丁内酯 、 乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 ethyl 6-hydroxy-3-oxohexanoate
  参考文献：
  名称：

  实用合成双环吡唑-5-酮衍生物

  摘要：

  该通信描述了在单锅反应程序中方便地合成稠合双环吡唑啉酮。还开发了改进的方案以高产率获得5,5-双环和大体积的吡唑啉酮。本文报道的方法代表了结构上多样化的双环吡唑啉酮的实用方法。

  DOI：

  10.1016/j.tetlet.2016.11.095

文献信息

• New developments in redox chemical delivery systems by means of 1,4-dihydroquinoline-based targetor: Application to galantamine delivery to the brain
  作者：Mihaela-Liliana Ţînţaş、Lénaïg Foucout、Sylvain Petit、Sylvain Oudeyer、Fabienne Gourand、Louisa Barré、Cyril Papamicaël、Vincent Levacher

  DOI：10.1016/j.ejmech.2014.05.022

  日期：2014.6

  The therapeutic efficiency of palliative treatments of AD, mostly based on acetylcholinesterase (AChE) inhibitors, is marred by serious adverse effects due to peripheral activity of these AChE inhibitors. In the literature, a redox-based chemical delivery system (CDS) has been developed to enhance drugs distribution to the brain while reducing peripheral side effects. Herein, we disclose two new synthetic strategies for the preparation of 1,4-dihydroquinoline/quinolinium salt redox-based systems particularly well designed for brain delivery of drugs sensitive to alkylation reactions. These strategies have been applied in the present case to the AChE inhibitor galantamine with the aim of alleviating adverse effects observed with cholinergic AD treatment. The first strategy is based on an intramolecular alkylation reaction as key step, whilst the second strategy relies on a useful coupling between galantamine and quinolinium salt key intermediate. In the course of this work, polymer-supported reagents and a solid-phase synthesis approach revealed to be highly helpful to develop this redox-based galantamine CDS. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Practical synthesis of bicyclic pyrazol-5-one derivatives
  作者：Xuejin Feng、Michael A. Xi、Yanjun Wu、Xiaogang Wang、Ning Xi

  DOI：10.1016/j.tetlet.2016.11.095

  日期：2017.1

  This communication describes a convenient synthesis of fused bicyclic pyrazolones in a one-pot reaction procedure. Modified protocols are also developed to access 5,5-bicyclic and bulky pyrazolones in good yields. The method reported herein represents a practical approach to structurally diversified bicyclic pyrazolones.

  该通信描述了在单锅反应程序中方便地合成稠合双环吡唑啉酮。还开发了改进的方案以高产率获得5,5-双环和大体积的吡唑啉酮。本文报道的方法代表了结构上多样化的双环吡唑啉酮的实用方法。