4-甲氧基-3-丁烯-2-酮 | 4652-27-1

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酮(含烯醇)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲氧基-3-丁烯-2-酮
• 英文名称: 4-methoxy-3-buten-2-one
• 英文别名: 4-methoxybut-3-en-2-one
• CAS: 4652-27-1
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: VLLHEPHWWIDUSS-UHFFFAOYSA-N

物化性质

• 沸点：
  200 °C(lit.)
• 密度：
  0.982 g/mL at 25 °C(lit.)
• 闪点：
  146 °F
• 溶解度：
  与四氢呋喃、乙醚、乙腈和苯混溶。
• 稳定性/保质期：
  常温常压下稳定，避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2914509090
• 危险类别码：
  R10
• 危险品运输编号：
  1224
• 危险性防范说明：
  P210,P273,P280,P305+P351+P338
• 危险性描述：
  H227,H317,H319,H412
• 储存条件：
  密封保存，应储存在阴凉干燥的库房中，冷藏温度为4℃。

SDS

Name:	4-Methoxy-3-buten-2-one Tech. 90% (GC) Material Safety Data Sheet
Synonym:
CAS:	4652-27-1

Section 1 - Chemical Product MSDS Name:4-Methoxy-3-buten-2-one Tech. 90% (GC) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4652-27-1	4-Methoxy-3-buten-2-one	90	225-087-4

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Aspiration may lead to pulmonary edema. Inhalation at high concentrations may cause CNS depression and asphixiation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Water may be ineffective.
Material is lighter than water and a fire may be spread by the use of water. Combustible liquid. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Containers may explode when heated.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 4652-27-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 200 deg C @ 760.00 mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: 63 deg C ( 145.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 0.9820 g/cm3
Molecular Formula: C5H8O2
Molecular Weight: 100.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong acids, strong bases, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4652-27-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Methoxy-3-buten-2-one - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4652-27-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4652-27-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4652-27-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用广泛的4-甲氧基-3-丁烯-2-酮是一种重要的有机合成中间体和医药中间体，在实验室研发和生物化工生产中有着广泛的应用。

反应信息

• 作为反应物：
  描述：

  4-甲氧基-3-丁烯-2-酮 在 ytterbium(III) triflate 作用下， 以 氯仿 为溶剂， 反应 168.0h， 以45%的产率得到三乙酰基苯
  参考文献：
  名称：

  亚胺和烯酮之间反应中的其他串联环化途径

  摘要：

  在路易斯酸性条件下或纯净条件下，二氢异喹啉与Danishefsky的二烯反应，生成低至中等产率的正式aza-Diels-Alder [4 + 2]-环加合物。但是，在路易斯酸催化下使用甲氧基乙烯基甲基酮并不能得到aza-Diels-Alder加合物，而是发生了正式的[2 + 2 + 2]-环加成反应，从而获得了二乙酰基二氢吡啶。路易斯酸负荷增加导致二氢吡啶的形成减少，相反，发生甲氧基乙烯基甲基酮的三聚反应，从而由不同的[2 + 2 + 2]-环加成反应生成1,3,5-三乙酰基苯。甲氧基乙烯基甲基酮的正式[4 + 2]-环加成反应需要环状的亚胺才能形成二氢吡啶，因为与无环亚胺的反应是由正式的[1 + 2 + 1 + 2]-环加成产生二氢吡啶的。3，4-二氢异喹啉和甲基乙烯基酮，由氧-亲路易斯酸催化，通过曼尼希-迈克尔途径和亚铵离子物种进行。所有反应均通过一锅级联途径进行。

  DOI：

  10.1016/j.tet.2016.01.006
• 作为产物：
  描述：

  4-methoxycarbonyloxy-but-3-en-2-one 在 magnesium(II) perchlorate 作用下， 以 苯 为溶剂， 生成 4-甲氧基-3-丁烯-2-酮
  参考文献：
  名称：

  Shramova,Z.I.; Skoldinov,A.P., Journal of Organic Chemistry USSR (English Translation), 1965, vol. 1, p. 1768 - 1772

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-甲氧基-3-丁烯-2-酮 、 3,3,3-三氟-2,2-二甲基丙酰氯 在 4-甲氧基-3-丁烯-2-酮 作用下， 以55的产率得到2-(1,1,1-trifluoro-2-methylpropan-2-yl)-4H-pyran-4-one
  参考文献：
  名称：

  Organic Compounds

  摘要：

  本发明涉及式（I）的化合物或其盐，其中取代基如描述中所定义，以及该化合物在治疗通过抑制磷脂酰肌醇3-激酶改善的疾病中的组合物和用途。

  公开号：

  US20100105711A1

文献信息

• [EN] FUSED HETEROCYCLIC DERIVATIVES AND USE THEREOF<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES FUSIONNÉS ET LEUR UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2009136663A1

  公开（公告）日：2009-11-12

  The present invention provides a fused heterocyclic derivative having a strong kinase inhibitory activity and use thereof. The present invention relates to a compound represented by the formula wherein each symbol is as defined in the present specification, or a salt thereof.

  本发明提供了一种具有强烈激酶抑制活性的融合杂环衍生物及其用途。本发明涉及本说明书中所定义的符号表示的化合物，或其盐。
• Regioselective Synthesis of 2-(Aryloxythio)benzoates by the First [3+3] Cyclizations of 3-Aryloxythio-1-silyloxybuta-1,3-dienes with 3-Alkoxy-2-en-1-ones
  作者：Peter Langer、Inam Iqbal、Muhammad Imran、Alexander Villinger

  DOI：10.1055/s-0028-1083287

  日期：2009.1

  Functionalized 2-(aryloxythio)benzoates were regio­selectively prepared by the first [3+3] cyclizations of 3-aryloxythio-1-trimethylsilyloxybuta-1,3-dienes with 3-alkoxy-2-en-1-ones. cyclizations - diaryl sulfides - regioselectivity - pyridines - silyl enol ethers

  通过3-芳氧基硫基-1-三甲基甲硅烷基氧基丁烯-1，3-二烯与3-烷氧基-2-烯-1-酮的第一个[3 + 3]环化来区域选择性地制备官能化的2-（芳氧基硫基）苯甲酸酯。 环化-二芳基硫醚-区域选择性-吡啶-甲硅烷基烯醇醚
• [EN] 2-PYRIDONE DERIVATIVES AS NETROPHIL ELASTASE INHIBITORS AND THEIR USE<br/>[FR] DERIVES 2-PYRIDONE UTILISES COMME INHIBITEURS D'ELASTASE NEUTROPHILE ET UTILISATION DE CEUX-CI
  申请人：ASTRAZENECA AB

  公开号：WO2005026124A1

  公开（公告）日：2005-03-24

  There are provided novel compounds of formula (I), wherein R1, R2, R4, R5, G1, G2, L, Y and n are as defined in the Specification and optical isomers, racemates and tautomers thereof, and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are inhibitors of neutrophil elastase.

  提供了式（I）的新化合物，其中R1、R2、R4、R5、G1、G2、L、Y和n如规范中定义的那样，以及其光学异构体、消旋体和互变异构体，以及其药学上可接受的盐；以及它们的制备方法、含有它们的组合物以及它们在治疗中的用途。这些化合物是中性粒细胞弹性蛋白酶的抑制剂。
• 2-Heteroaryl-pyrazolo-[4,3-e]-1,2,4-triazolo-[1,5-c]-pyrimidine adenosine A2a receptor antagonists
  申请人：Neustadt R. Bernard

  公开号：US20070066620A1

  公开（公告）日：2007-03-22

  Compounds having the structural formula I or a pharmaceutically acceptable salt thereof, wherein R is R 1 -isoxazolyl, R 1 -oxadiazolyl, R 1 -dihydrofuranyl, R 1 -pyrazolyl, R 1 -imidazolyl, R 1 -pyrazinyl or R 1 -pyrimidinyl; R 1 is 1, 2 or 3 substituents selected from H, alkyl, alkoxy and halo; Z is optionally substituted-aryl, or optionally substituted-heteroaryl; are disclosed, as well as their use in the treatment of central nervous system diseases, in particular Parkinson's disease and Extra Pyramidal Syndrome, pharmaceutical compositions comprising them, and combinations with other agents.

  具有结构式I或其药用可接受盐的化合物，其中R是R1-异噁唑基、R1-噁唑啉基、R1-二氢呋喃基、R1-吡唑基、R1-咪唑基、R1-吡啶基或R1-嘧啶基；R1是从H、烷基、烷氧基和卤代中选择的1、2或3个取代基；Z是可选择取代的芳基或可选择取代的杂芳基；公开了这些化合物及其在治疗中枢神经系统疾病，特别是帕金森病和额外锥体综合征中的用途，包括它们的药物组合物和与其他药剂的组合。
• [EN] COMPOUNDS AND THEIR METHODS OF USE<br/>[FR] COMPOSÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：PRAXIS PREC MEDICINES INC

  公开号：WO2018098500A1

  公开（公告）日：2018-05-31

  The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

  本发明部分涉及融合的杂环化合物和组合物，用于预防和/或治疗与电压门控钠离子通道异常功能相关的疾病或病况，例如异常的晚期/持续性钠电流。本文还提供了治疗与钠离子通道异常功能相关的疾病或病况的方法，包括德拉维特综合征或癫痫。