ethyl 1-(4-chlorobenzyl)piperidine-4-carboxylate | 308109-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ethyl 1-(4-chlorobenzyl)piperidine-4-carboxylate
• 英文别名: ethyl 1-[(4-chlorophenyl)methyl]piperidine-4-carboxylate
• CAS: 308109-90-2
• 化学式: C₁₅H₂₀ClNO₂
• mdl: MFCD00810471
• 分子量: 281.782
• InChiKey: GDOIAXSRNZFHOU-UHFFFAOYSA-N

物化性质

• 沸点：
  354.5±37.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-chlorobenzyl)piperidine-4-carboxylate 在 sodium hydroxide 、 水 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到sodium 1-(4'-chlorobenzyl)isonipecotate
  参考文献：
  名称：

  CYCLIC AMINE DERIVATIVES AND THEIR USES

  摘要：

  公开号：

  EP1181278B1
• 作为产物：
  描述：

  哌啶-4-甲酸乙酯 、 4-氯氯苄 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以75%的产率得到ethyl 1-(4-chlorobenzyl)piperidine-4-carboxylate
  参考文献：
  名称：

  CYCLIC AMINE DERIVATIVES AND THEIR USES

  摘要：

  公开号：

  EP1181278B1

文献信息

• Direct Reductive Amination of Carbonyl Compounds with H ₂ Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N‐Alkylation with Alkyl Halides
  作者：Benjamin Laroche、Haruro Ishitani、Shū Kobayashi

  DOI：10.1002/adsc.201801457

  日期：2018.12.21

  continuous‐flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C−N bonds without production of any hazardous

  据报道，一般的连续流方法可直接将仲胺和伯胺与芳香族和脂肪族醛以及酮进行直接还原胺化。关键是要使用氢气和可商购的Pt / C作为非均相催化剂。除了具有出色的官能团耐受性外，该方法还可以快速形成C-N键，而不会产生任何危险的化学废料。还描述了在合成关键中间体以生产活性药物成分方面的应用（Donepezil和Arformoterol / Tamsulosin）。
• Novel 1,2,4-oxadiazole derivatives as selective butyrylcholinesterase inhibitors: Design, synthesis and biological evaluation
  作者：Akbarzadeh, Tahmineh、Hariri, Roshanak、Nazari, Maryam、Rezaee, Elham、Tabatabai, Sayyed Abbas

  DOI：10.17179/excli2021-3569

  日期：——

  Alzheimer’s disease (AD) is a progressive mental disorder that brings a huge economic burden to the healthcare systems. During this illness, acetylcholine levels in the cholinergic systems gradually diminish, which results in severe memory loss and cognitive impairments. Moreover, Butyrylcholinesterase (BuChE) enzyme participates in cholinergic neurotransmission regulation by playing a prominent role in the latter phase of AD. In this study, based on donepezil, which is an effective acetylcholinesterase (AChE) inhibitor, a series of 1,2,4-oxadiazole compounds were designed, synthesized and their inhibitory activities towards AChE and BuChE enzymes were evaluated. Some structures exhibited a higher selectivity rate towards BuChE in comparison to donepezil. Notably, compound 6n with an IC50 value of 5.07 µM and an SI ratio greater than 19.72 showed the highest potency and selectivity towards BuChE enzyme. The docking result revealed that compound 6n properly fitted the active site pocket of BuChE enzyme, and formed desirable lipophilic interactions and hydrogen bonds. Moreover, according to in silico ADME studies, these compounds have proper potential for being developed as new oral anti-Alzheimer’s agents.

  阿尔茨海默病（AD）是一种渐进性精神疾病，给医疗系统带来了巨大的经济负担。患病期间，胆碱能系统中的乙酰胆碱水平会逐渐降低，从而导致严重的记忆丧失和认知障碍。此外，丁酰胆碱酯酶（BuChE）参与胆碱能神经递质的调节，在 AD 的后期阶段发挥着重要作用。多奈哌齐是一种有效的乙酰胆碱酯酶（AChE）抑制剂，本研究以多奈哌齐为基础，设计、合成了一系列 1,2,4-噁二唑化合物，并评估了它们对 AChE 和 BuChE 酶的抑制活性。与多奈哌齐相比，一些结构对 BuChE 具有更高的选择性。值得注意的是，IC50 值为 5.07 µM、SI 比大于 19.72 的化合物 6n 对 BuChE 酶具有最高的效力和选择性。对接结果表明，化合物 6n 与 BuChE 酶的活性位点口袋十分吻合，并形成了理想的亲脂相互作用和氢键。此外，根据硅学 ADME 研究，这些化合物具有开发为新型口服抗阿尔茨海默氏症药物的适当潜力。
• US7125895B1
  申请人：——

  公开号：US7125895B1

  公开（公告）日：2006-10-24
• CYCLIC AMINE DERIVATIVES AND THEIR USES
  申请人：Bristol-Myers Squibb Pharma Research Labs, Inc.

  公开号：EP1181278B1

  公开（公告）日：2004-09-29