ethyl 1-(2-ethoxy-2-oxoethyl)-4-fluoropiperidine-4-carboxylate | 1426832-18-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 1-(2-ethoxy-2-oxoethyl)-4-fluoropiperidine-4-carboxylate
• 英文别名: Ethyl 1-(2-ethoxy-2-oxoethyl)-4-fluoropiperidine-4-carboxylate
• CAS: 1426832-18-9
• 化学式: C₁₂H₂₀FNO₄
• 分子量: 261.294
• InChiKey: OVKPLPCRRZLTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-(2-ethoxy-2-oxoethyl)-4-fluoropiperidine-4-carboxylate 在 高氯酸 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 4-Fluoro-1-azabicyclo[2.2.2]octane-3-carbaldehyde
  参考文献：
  名称：

  Discovery of a novel series of quinolone α7 nicotinic acetylcholine receptor agonists

  摘要：

  High throughput screening led to the identification of a novel series of quinolone alpha 7 nicotinic acetylcholine receptor (nAChR) agonists. Optimization of an HTS hit (1) led to 4-phenyl-1-(quinuclidin-3-ylmethyl)quinolin-2(1H)-one, which was found to be potent and selective. Poor brain penetrance in this series was attributed to transporter-mediated efflux, which was in turn due to high pK(a). A novel 4-fluoroquinuclidine significantly lowered the pK(a) of the quinuclidine moiety, reducing efflux as measured by a Caco-2 assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.070
• 作为产物：
  描述：

  N-Boc-4-氟-4-哌啶甲酸乙酯 在 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 ethyl 1-(2-ethoxy-2-oxoethyl)-4-fluoropiperidine-4-carboxylate
  参考文献：
  名称：

  有机铁电涡-反涡畴结构

  摘要：

  有机铁电体因其机械灵活性、易于制造和低声阻抗而引起了极大的兴趣。尽管近年来取得了很大进展，但在有机铁电系统中，诸如涡流之类的拓扑缺陷仍然相对未被探索。在这里，我们从 [quinuclidinium]ReO4 ([Q]ReO4) 中应用 H/F 取代的分子设计策略成功合成了有机铁电体 [4-氟奎宁环]ReO4 ([4-FQ]ReO4)。通过 H/F 取代，居里温度和自发极化分别从 [Q]ReO4 中的 367 K 和 5.83 μC/cm2 增加到 [4-FQ]ReO4 中的 466 K 和 11.37 μC/cm2。此外，在机械应力场下，在[4-FQ]ReO4薄膜中出现了三种不同偏振方向的条纹状畴，形成了风车状的畴图案，其中可以稳定存在有趣的涡旋-反涡旋拓扑配置。这项工作为优化有机铁电体的性质和探索新兴现象提供了一种有效的策略。

  DOI：

  10.1021/jacs.0c11416

文献信息

• [EN] QUINUCLIDINE-3-ONE DERIVATIVES<br/>[FR] DÉRIVÉS DE QUINUCLIDINE-3-ONE
  申请人：[en]APREA THERAPEUTICS AB

  公开号：WO2022175402A1

  公开（公告）日：2022-08-25

  The invention relates to certain substituted quinuclidine-3-one compounds for use in the treatment of hyperproliferative disease, such as cancer, and diseases associated with inflammation. More particularly, the present invention relates to certain substituted 3-quinuclidinones, pharmaceutically acceptable salts thereof, pharmaceutical compositions containing the same, and to methods for using such compounds. In this manner, these compounds are of use for treating hyperproliferative diseases and inflammatory diseases.
• Discovery of a novel series of quinolone α7 nicotinic acetylcholine receptor agonists
  作者：Ivar M. McDonald、Robert A. Mate、F. Christopher Zusi、Hong Huang、Debra J. Post-Munson、Meredith A. Ferrante、Lizbeth Gallagher、Robert L. Bertekap、Ronald J. Knox、Barbara J. Robertson、David G. Harden、Daniel G. Morgan、Nicholas J. Lodge、Steven I. Dworetzky、Richard E. Olson、John E. Macor

  DOI：10.1016/j.bmcl.2013.01.070

  日期：2013.3

  High throughput screening led to the identification of a novel series of quinolone alpha 7 nicotinic acetylcholine receptor (nAChR) agonists. Optimization of an HTS hit (1) led to 4-phenyl-1-(quinuclidin-3-ylmethyl)quinolin-2(1H)-one, which was found to be potent and selective. Poor brain penetrance in this series was attributed to transporter-mediated efflux, which was in turn due to high pK(a). A novel 4-fluoroquinuclidine significantly lowered the pK(a) of the quinuclidine moiety, reducing efflux as measured by a Caco-2 assay. (C) 2013 Elsevier Ltd. All rights reserved.
• Organic Ferroelectric Vortex–Antivortex Domain Structure
  作者：Yuan-Yuan Tang、Yongfa Xie、Yong Ai、Wei-Qiang Liao、Peng-Fei Li、Takayoshi Nakamura、Ren-Gen Xiong

  DOI：10.1021/jacs.0c11416

  日期：2020.12.30

  Organic ferroelectrics are attracting tremendous interest because of their mechanical flexibility, ease of fabrication, and low acoustical impedance. Although great advances have been made in recent years, topological defects such as vortices remain relatively unexplored in the organic ferroelectric system. Here, from [quinuclidinium]ReO4 ([Q]ReO4), we applied the molecular design strategy of H/F substitution

  有机铁电体因其机械灵活性、易于制造和低声阻抗而引起了极大的兴趣。尽管近年来取得了很大进展，但在有机铁电系统中，诸如涡流之类的拓扑缺陷仍然相对未被探索。在这里，我们从 [quinuclidinium]ReO4 ([Q]ReO4) 中应用 H/F 取代的分子设计策略成功合成了有机铁电体 [4-氟奎宁环]ReO4 ([4-FQ]ReO4)。通过 H/F 取代，居里温度和自发极化分别从 [Q]ReO4 中的 367 K 和 5.83 μC/cm2 增加到 [4-FQ]ReO4 中的 466 K 和 11.37 μC/cm2。此外，在机械应力场下，在[4-FQ]ReO4薄膜中出现了三种不同偏振方向的条纹状畴，形成了风车状的畴图案，其中可以稳定存在有趣的涡旋-反涡旋拓扑配置。这项工作为优化有机铁电体的性质和探索新兴现象提供了一种有效的策略。