2-戊酰基-吡啶 | 7137-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-戊酰基-吡啶
• 中文别名: 1-(2-吡啶基)-1-戊酮
• 英文名称: 1-(pyridin-2-yl)pentan-1-one
• 英文别名: 1-(2-pyridinyl)-1-pentanone；1-pyridin-2-ylpentan-1-one
• CAS: 7137-97-5
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: DGBHHRPKPZCABG-UHFFFAOYSA-N

物化性质

• 沸点：
  249℃
• 密度：
  0.997
• 闪点：
  111℃
• 保留指数：
  1297

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(Pyridin-2-yl)pentan-1-one
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-(Pyridin-2-yl)pentan-1-one
CAS number: 7137-97-5

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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: C10H13NO
Molecular weight: 163.2

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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

反应信息

• 作为反应物：
  描述：

  2-戊酰基-吡啶 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 N'-(1-Pyridin-2-yl-pentyl)-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5- b ]quinoline-1,4,10(5 H )-triones as NMDA glycine-site antagonists

  摘要：

  Several members of the 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones (2) have been identified as being potent and selective NMDA glycine-site antagonists. Increasing size of the alkyl substituent on the alpha-carbon led to a progressive decrease in binding affinity. Some of these analogues possess improved drug-like properties such as cellular permeability, solubility and oral absorption. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00750-9
• 作为产物：
  描述：

  谷胱甘肽 以 aq. phosphate buffer 为溶剂， 反应 2.08h， 生成 2-戊酰基-吡啶
  参考文献：
  名称：

  葡萄糖，谷胱甘肽和脂肪醛的加热模型系统中初始反应中间体的表征。

  摘要：

  为了了解脂质降解对肉味风味素的美拉德形成的影响，通过以下方法鉴定了葡萄糖-谷胱甘肽与己醛，（E）-2-庚烯或（E，E）-2,4-癸二烯醛的模型系统中的初始反应中间体HPLC-MS和通过NMR。除Amadori化合物外，还发现了通过将巯基加成到羰基或共轭的烯键上的半缩醛和噻唑烷。所有中间体的浓度随反应时间而增加，而具有谷胱甘肽部分的中间体的降解则有助于半胱氨酰甘氨酸形成噻唑烷。不饱和醛（E）-2-庚醛和（E，E）-2,4-癸二醛对谷胱甘肽显示出对葡萄糖的高反应性，比从葡萄糖中产生更高水平的中间体化合物。加热制备的中间体可逆地释放出原始醛，导致由逆醛醇，氧化等形成的各种化合物与H2S和NH3反应。其中，首次提出了包括3-壬烯-2-酮，2-己酰基呋喃和六个二烷基噻吩（例如2-乙基-5-（1-甲基丁基）噻吩）的形成途径。

  DOI：

  10.1016/j.foodchem.2019.125482

文献信息

• Room Temperature Metal-Catalyzed Oxidative Acylation of Electron-Deficient Heteroarenes with Alkynes, Its Mechanism, and Application Studies
  作者：Shweta Sharma、Mukesh Kumar、Ram A. Vishwakarma、Mahendra K. Verma、Parvinder Pal Singh

  DOI：10.1021/acs.joc.8b01475

  日期：2018.10.19

  room-temperature, regioselective Minisci reaction for the acylation of electron-deficient heteroarenes with alkynes. The method has broad functional group compatibility and gives exclusively monoacylated products in good to excellent yields. The mechanistic pathway was analyzed based on a series of experiments confirming the involvement of a radical pathway. The 18O-labeling experiment suggested that water

  在这里，我们报告原始的一步式，简单的，室温，区域选择性Minisci反应，用于炔烃与缺电子的杂芳烃的酰化反应。该方法具有广泛的官能团相容性，并以良好至极佳的收率提供仅单酰化的产物。基于一系列实验证实了自由基途径的参与，对机械途径进行了分析。的18 O型标记实验表明，水是氧在酰化产物的源极，和头部空间GC-MS实验表明通过释放发生的C-C切割为CO 2。
• Continuous Flow Synthesis of Ketones from Carbon Dioxide and Organolithium or Grignard Reagents
  作者：Jie Wu、Xiaoqing Yang、Zhi He、Xianwen Mao、T. Alan Hatton、Timothy F. Jamison

  DOI：10.1002/anie.201405014

  日期：2014.8.4

  describe an efficient continuous flow synthesis of ketones from CO2 and organolithium or Grignard reagents that exhibits significant advantages over conventional batch conditions in suppressing undesired symmetric ketone and tertiary alcohol byproducts. We observed an unprecedented solvent‐dependence of the organolithium reactivity, the key factor in governing selectivity during the flow process. A facile

  我们描述了由CO 2和有机锂或格氏试剂的有效连续流动合成酮，在抑制不希望的对称酮和叔醇副产物方面，与常规间歇条件相比，它显示出显着优势。我们观察到有机锂反应性的前所未有的溶剂依赖性，这是控制流动过程中选择性的关键因素。还建立了一种通过在线生成有机金属试剂以模块化方式制备酮的简便，可伸缩的三步一流工艺。
• Behaviour ofN-Pyridylbenzamides versus Benzanilides in theortho-Directed Lithiation of Masked Aromatic Carboxylic Acids
  作者：Andrzej Jóźwiak、Jacek Z. Brzeziński、Mieczysław W. Płotka、Aleksandra K. Szcześniak、Zbigniew Malinowski、Jan Epsztajn

  DOI：10.1002/ejoc.200400156

  日期：2004.8

  examined. The perfect selectivity that has been observed until now in the lithiation of anilides, a reaction used for ortho-functionalisation of masked aromatic carboxylic acids, has been broken; our results indicate that the pyridine ring at the position ortho to the directed metallation group is more susceptible to lithiation than the homoaromatic ring itself. This was proved in an intermolecular comparative

  研究了 N-吡啶基苯甲酰胺 1-3 与正丁基锂或仲丁基锂的反应。迄今为止，在苯胺锂化（一种用于掩蔽芳香羧酸的邻位官能化的反应）中观察到的完美选择性已被打破；我们的结果表明，在定向金属化基团邻位的吡啶环比同芳环本身更容易被锂化。这在对苯甲酸、吡啶甲酸苯胺和异烟酰苯胺 14-16 和 N-枯基苯甲酰胺 (17) 的分子间比较研究中得到证实。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• REACTION OF (<i>E</i>)-PHENYL 2-PYRIDYL KETONE<i>O</i>-ACYLOXIMES (PPAO) WITH GRIGNARD REAGENTS. A CONVENIENT AND HIGHLY CHEMOSELECTIVE SYNTHESIS OF KETONES
  作者：Tadayo Miyasaka、Hideaki Monobe、Shunsaku Noguchi

  DOI：10.1246/cl.1986.449

  日期：1986.4.5

  The reaction of (E)-phenyl 2-pyridyl ketone O-acyloximes (PPAO) with Grignard reagents was found to be widely applicable to the chemoselective synthesis of various ketones in good yields under mild conditions.

  发现 (E)-苯基 2-吡啶基酮 O-酰基肟 (PPAO) 与格氏试剂的反应广泛适用于在温和条件下以良好的收率对各种酮进行化学选择性合成。
• Ru₃(CO)₁₂-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2 + 2 + 1] Cycloaddition Strategy for the Synthesis of Functionalized γ-Butyrolactones
  作者：Mamoru Tobisu、Naoto Chatani、Taku Asaumi、Katsuya Amako、Yutaka Ie、Yoshiya Fukumoto、Shinji Murai

  DOI：10.1021/ja003018i

  日期：2000.12.1

  The ruthenium-catalyzed intermolecular cyclocoupling of ketones (or aldehydes), alkenes (or alkynes), and CO, which leads to γ-butyrolactones, is described. The reaction represents the first example of the catalytic synthesis of heterocycles via an intermolecular carbonylative [2 + 2 + 1] cycloaddition. A wide variety of ketones, such as α-dicarbonyl compounds and N-heterocyclic ketones, can be used

  描述了钌催化的酮（或醛）、烯烃（或炔烃）和 CO 的分子间环偶联，这导致了 γ-丁内酯。该反应代表了通过分子间羰基化 [2 + 2 + 1] 环加成催化合成杂环的第一个例子。在这种环加成反应中可以使用多种酮，例如 α-二羰基化合物和 N-杂环酮。加入膦对α-二羰基化合物的反应非常有效。在检查的膦中，P(4-CF3C6H4)3 代表了选择的添加剂。环状烯烃、未极化的末端烯烃和内炔可成功用于合成高度官能化的内酯。在芳族酮酯的芳族部分引入CF3基团加速了酮酯与乙烯的反应，而引入MeO基团则提高了N-杂环酮与乙烯的反应速率。反应速率增加...

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