4-哌啶乙酸乙酯 | 59184-90-6

• 物质功能分类: 医药中间体
• 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
• 中文名称: 4-哌啶乙酸乙酯
• 中文别名: 4-哌啶乙酸甲酯
• 英文名称: ethyl (piperidin-4-yl)acetate
• 英文别名: ethyl 4-piperidinylacetate；ethyl 2-(piperidin-4-yl)acetate；ethyl 2-(4-piperidyl)acetate；ethyl 2-piperidin-4-ylacetate
• CAS: 59184-90-6
• 化学式: C₉H₁₇NO₂
• mdl: MFCD02183575
• 分子量: 171.239
• InChiKey: IHSUFLCKRIHFGY-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C (decomp)
• 沸点：
  67°C/0.22mm
• 密度：
  0.969±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免接触水。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  在密封的贮藏器中，应将其置于阴凉、干燥处并保持良好通风保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Piperidin-4-yl)-acetic acid ethyl ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-(Piperidin-4-yl)-acetic acid ethyl ester
CAS number: 59184-90-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H17NO2
Molecular weight: 171.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

哌啶类衍生物作为药物中间体，在医药领域具有重要的研究价值。4-哌啶乙酸甲酯也是一种重要的哌啶类衍生物药物中间体。然而，目前我国还没有真正实现工业化的制备装置，主要依赖相应的哌啶衍生物为原料，通过使用昂贵的催化剂（如氧化铂、Pd/C或Raney Ni）和苛刻的反应条件（高温高压）来合成。这种方法虽然可以得到产物，但收率较低且成本高昂，不适合大规模工业化生产。

用途

4-哌啶乙酸甲酯作为药物中间体，在医药领域主要用于合成治疗神经性疾病的药物，如抗惊厥、抗癫痫和镇静剂等。

反应信息

• 作为反应物：
  描述：

  4-哌啶乙酸乙酯 在 水 、 sodium carbonate 作用下， 反应 2.0h， 生成 4-哌啶乙酸
  参考文献：
  名称：

  矩阵的强效发现，选择性，和口服活性羧酸基于金属蛋白酶抑制剂-13 †

  摘要：

  基质金属蛋白酶MMP-13在骨关节炎（OA）的软骨和骨骼的II型胶原降解中起关键作用。因此，有效的MMP-13抑制剂将是用于治疗关节炎的新型疾病改良疗法。我们的努力导致发现了一系列MMP-13羧酸抑制剂，它们不会显着抑制相关的MMP-1（胶原酶-1）或肿瘤坏死因子-α（TNF-α）转化酶（TACE）。先前已经提出（但尚未证明）抑制后两种酶可能导致副作用。鉴定出有前途的羧酸铅9并开发了收敛的合成方法。本文介绍了9的优化和化合物24f的鉴定进一步发展。化合物24f是MMP-13的亚纳摩尔抑制剂（IC 50值为0.5 nM，K i为0.19 nM），对MMP-1或TACE无活性（IC 50大于10000 nM）。此外，在MMP-13诱导的软骨降解的大鼠模型中，口服30 mg / kg（75％抑制，p <0.05）和10 mg / kg（40％抑制，p < 0.05）口服后，蛋白24f显着降低蛋白聚糖的释放。0

  DOI：

  10.1021/jm801394m
• 作为产物：
  描述：

  4-羟基-1-哌啶甲酸苄酯 在 palladium on activated charcoal 、 乙二胺 氢气 、 silica gel 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 47.75h， 生成 4-哌啶乙酸乙酯
  参考文献：
  名称：

  Pd/C(en)-Catalyzed Chemoselective Hydrogenation with Retention of the N-Cbz Protective Group and its Scope and Limitations

  摘要：

  A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis (C) 2000 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4020(00)00771-7

文献信息

• LTA4H modulators and uses thereof
  申请人：Barchuk William T.

  公开号：US20080194630A1

  公开（公告）日：2008-08-14

  Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation.

  白三烯A4水解酶（LTA4H）抑制剂，含有它们的组合物，以及用于抑制LTA4H酶活性和治疗、预防或抑制炎症和/或与炎症相关疾病的方法。
• HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS
  申请人：SUVEN LIFE SCIENCES LIMITED

  公开号：US20140187581A1

  公开（公告）日：2014-07-03

  The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT 4 receptors.

  本发明涉及式(I)的新化合物，以及它们的药用盐和含有它们的组合物。 本发明还涉及制备上述新化合物的方法，以及它们的药用盐。式(I)的化合物在治疗与5-HT 4 受体相关的各种疾病中是有用的。
• [EN] AUTOTAXIN INHIBITORS COMPRISING A HETEROAROMATIC RING-BENZYL-AMIDE-CYCLE CORE<br/>[FR] INHIBITEURS DE L'AUTOTAXINE CONTENANT UN NOYAU À CYCLE BENZYLE-AMIDE CYCLIQUE HÉTÉROAROMATIQUE
  申请人：NOVARTIS AG

  公开号：WO2015008230A1

  公开（公告）日：2015-01-22

  The present invention relates to novel compounds that are autotaxin inhibitors, processes for their preparation, pharmaceutical compositions and medicaments containing them and to their use in diseases and disorders mediated by autotaxin.

  本发明涉及新型化合物，这些化合物是自体磷脂酶抑制剂，涉及它们的制备方法，含有它们的药物组合物和药物，以及它们在由自体磷脂酶介导的疾病和紊乱中的应用。
• Practical and regioselective amination of arenes using alkyl amines
  作者：Alessandro Ruffoni、Fabio Juliá、Thomas D. Svejstrup、Alastair J. McMillan、James J. Douglas、Daniele Leonori

  DOI：10.1038/s41557-019-0254-5

  日期：2019.5

  these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C-H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process

  用于制备芳香胺的碳-氮键的形成是全球范围内为生产高价值材料而进行的前五项反应之一，从原料化学品到药物和聚合物不等。由于这种普遍性和多样性，其制备方法影响了学术界和工业界的整个化学合成过程。通常，这些分子是通过逐步引入反应性手柄代替芳香族CH键（即硝基，卤素或硼酸）和随后的功能化或交叉偶联而组装而成的。在这里，我们表明，芳烃胺可以使用光催化作用，通过芳烃和烷基胺的直接反应来构建，而无需进行预功能化。该过程可以轻松准备高级构建基块，容忍的功能范围很广，并且可以通过批处理流协议来实现多克规模。通过对几种药物，农药，肽，手性催化剂，聚合物和有机金属配合物的修饰，证明了该策略作为后期功能化平台的优点。
• CHROMOGENIC PEROXIDASE SUBSTRATES
  申请人：Dako Denmark A/S

  公开号：US20170175178A1

  公开（公告）日：2017-06-22

  Chromogenic conjugates for color-based detection of targets are described. The conjugates comprise a chromogenic moiety such as rhodamine, rhodol or fluorescein. The chromogenic moiety is linked to a peroxidase substrate. The chromogenic conjugates can be used in immunohistochemical analysis and in situ hybridization. The conjugates can be used to detect 1, 2, 3 or more targets in a sample by color.

  描述了用于基于颜色的目标检测的色素结合物。这些结合物包含一个色素部分，例如罗丹明、罗丹醇或荧光素。色素部分与过氧化物酶底物相连。色素结合物可用于免疫组织化学分析和原位杂交。这些结合物可以通过颜色检测样品中的1个、2个、3个或更多目标。