1-(2-(4-硝基苯氧基)乙基)哌啶 | 92033-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-(4-硝基苯氧基)乙基)哌啶
• 英文名称: 1-(2-(4-nitrophenoxy)ethyl)piperidine
• 英文别名: 1-[2-(1-piperidinyl)ethoxy]4-nitrobenzene；1-[2-(4-nitrophenoxy)ethyl]piperidine
• CAS: 92033-76-6
• 化学式: C₁₃H₁₈N₂O₃
• mdl: MFCD01308502
• 分子量: 250.298
• InChiKey: HLQQRQNEDYOBHS-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  393.6±22.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(2-(4-Nitrophenoxy)ethyl)piperidine
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: 1-(2-(4-Nitrophenoxy)ethyl)piperidine
CAS number: 92033-76-6

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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: C13H18N2O3
Molecular weight: 250.3

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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

反应信息

• 作为反应物：
  描述：

  1-(2-(4-硝基苯氧基)乙基)哌啶 在 10% Pt/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 4-(2-哌啶-1-乙氧基)-苯胺
  参考文献：
  名称：

  一系列新型ebselen衍生物的合成和生物学评估，如谷胱甘肽过氧化物酶（GPx）模拟物和胆碱酯酶抑制剂，可预防阿尔茨海默氏病

  摘要：

  设计，合成和评估了一系列依布硒仑衍生物，作为胆碱酯酶（ChEs）和谷胱甘肽过氧化物酶（GPx）模拟物的抑制剂。发现大多数化合物对AChE和BuChE均有效，化合物5e和5i被证明对AChE最有效，IC 50值分别为0.76和0.46μM。在这些杂种中，与ebselen相比，发现大多数化合物都是良好的GPx模拟物。所选择的化合物5e和5i还用于确定催化参数和体外过氧化氢清除活性。结果表明化合物5e和5i 可能是治疗AD的优秀多功能药物。

  DOI：

  10.1016/j.bmc.2013.12.066
• 作为产物：
  描述：

  2-(4-硝基苯氧基)乙醇 在 吡啶 、 氯化亚砜 、 potassium carbonate 、 potassium iodide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(2-(4-硝基苯氧基)乙基)哌啶
  参考文献：
  名称：

  设计，合成，生物学评估和分子对接研究靶向ERα的新型3-芳基-4-苯胺基-2H-铬基-2-酮衍生物作为抗乳腺癌药物。

  摘要：

  雌激素受体（ER）在乳腺癌的发展和进程中起着重要作用，并且是抗癌药物发现的主要目标。为了开发新颖的选择性ERα调节剂（SERM），我们基于先前报道的先导化合物设计并合成了18种新颖的3-芳基-4-苯胺基-2H-色烯-2-酮衍生物。生物学结果表明，与阳性对照他莫昔芬相比，大多数化合物具有有效的ERα结合亲和力，并且对MCF-7和Ishikawa细胞系具有更好的抗增殖活性。哌啶基取代的化合物（例如16d和18d）分别具有很强的ERα结合亲和力和出色的抗增殖活性。化合物18d显示最有效的ERα结合亲和力，RBA值为2.83％，16d对MCF-7细胞表现出最佳的抗增殖活性，IC50值为4.52±2.47μM。还进行了进一步的分子对接研究，以研究新合成的化合物与ERα的结合模式。所有这些结果以及结构-活性关系（SAR）表明，这些具有碱性侧链的3-芳基-4-苯胺基-2H-铬-2-基衍生物可以作为进一步优化新型SERM的有前途的线索。

  DOI：

  10.1016/j.bmcl.2017.04.029

文献信息

• Phenyl and pyridyl LTA4H modulators
  申请人：Butler R. Christopher

  公开号：US20060223792A1

  公开（公告）日：2006-10-05

  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 inflammatory conditions.

  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、预防或抑制炎症和炎症症状的方法。
• Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids
  作者：Rolf Norén

  DOI：10.1016/j.tet.2021.132108

  日期：2021.5

  A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3•Me2S

  评价了新的保护基2-（哌啶-1-基）-乙基（PIP）作为酚的保护基。PIP基团在原锂化条件下稳定，并在浓氢溴酸中回流。脱保护可通过两种途径完成，即氧化为N-氧化物，然后进行Cope消除（CE），然后进行乙烯基醚的水解或臭氧分解，或通过BBr 3 •Me 2 S进行一步脱保护。PIP基团与O-正交。苄基，O-乙酰基，Ot-丁基二苯基甲硅烷基，O-甲基，Op-甲氧基苄基，O-烯丙基，O-四氢吡喃基和Nt-丁氧基羰基。对CE步骤进行了系统地研究，发现当在甲硅烷基化剂存在下进行反应时，可以提高收率。
• Design, Synthesis and Biological Evaluation of Pyridin-3-yl pyrimidines as Potent Bcr-Abl Inhibitors
  作者：Xiaoyan Pan、Jinyun Dong、Hongping Gao、Fang Wang、Yanmin Zhang、Sicen Wang、Jie Zhang

  DOI：10.1111/cbdd.12272

  日期：2014.5

  The preliminary results indicated that some compounds were promising anticancer agents. Compounds A2, A8, and A9 exhibited potent Bcr‐Abl inhibitory activity, suggesting that aniline containing halogen substituents might be important for biological activity. Molecular docking was carried out to investigate the binding mode of them with Bcr‐Abl. Details of synthesis and SAR studies of these compounds are

  合成了一系列的吡啶-3-基嘧啶，并对其Bcr-Abl抑制和抗癌活性进行了评估。初步结果表明，某些化合物是有前途的抗癌药。化合物A2，A8和A9表现出强大的Bcr-Abl抑制活性，表明含卤素取代基的苯胺可能对生物活性很重要。进行了分子对接以研究它们与Bcr-Abl的结合模式。描述了这些化合物的合成和SAR研究的细节。
• 3-(Arylamino)methylene-1, 3-dihydro-2H-indol-2-ones as kinase inhibitors
  申请人：——

  公开号：US20030199478A1

  公开（公告）日：2003-10-23

  The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

  本发明涉及有机分子，能够调节酪氨酸激酶信号传导，以调控、调节和/或抑制异常细胞增殖。
• METHOD OF TREATING NEURODEGENERATIVE DISORDERS VIA INHIBITION OF AMYLOID BETA PEPTIDE BINDING
  申请人：——

  公开号：US20020013374A1

  公开（公告）日：2002-01-31

  The invention is directed to a method of treating a neurodegenerative disorder in a subject in need thereof which comprises administering to the subject an amount of a compound effective to inhibit the interaction of amyloid-beta with alpha-7 nicotinic acetylcholine receptors.

  本发明涉及一种治疗神经退行性疾病的方法，包括向需要治疗的受体注射足够的化合物，以抑制淀粉样蛋白-β与α-7尼古丁乙酰胆碱受体的相互作用。