4-乙酰基-5-甲基异恶唑-3-甲酸乙酯 | 15911-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基-5-甲基异恶唑-3-甲酸乙酯
• 中文别名: 5-乙基异噁唑-3,4-二羧酸二乙酯；4-乙酰-5-甲基异恶唑-3-羧酸乙酯
• 英文名称: ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate
• 英文别名: Ethyl 4-acetyl-5-methylisoxazole-3-carboxylate；ethyl 4-acetyl-5-methyl-1,2-oxazole-3-carboxylate
• CAS: 15911-11-2
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: KABXFHWGNZLDTD-UHFFFAOYSA-N

物化性质

• 沸点：
  102 °C
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 储存条件：
  室温

SDS

Name:	Ethyl 4-acetyl-5-methylisoxazole-3-carboxylate Material Safety Data Sheet
Synonym:
CAS:	15911-11-2

Section 1 - Chemical Product MSDS Name:Ethyl 4-acetyl-5-methylisoxazole-3-carboxylate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15911-11-2	Ethyl 4-acetyl-5-methylisoxazole-3-car	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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. Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 15911-11-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 110 deg C @0.3mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H11NO4
Molecular Weight: 197.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15911-11-2: NY2360000 LD50/LC50:
CAS# 15911-11-2: Oral, rat: LD50 = 1 gm/kg.
Carcinogenicity:
Ethyl 4-acetyl-5-methylisoxazole-3-carboxylate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 15911-11-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15911-11-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15911-11-2 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

反应信息

• 作为反应物：
  描述：

  4-乙酰基-5-甲基异恶唑-3-甲酸乙酯 在 sodium hydroxide 、 五氯化磷 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 4-acetyl-5-methyl-isoxazole-3-carboxylic acid anilide
  参考文献：
  名称：

  Dal Piaz,V.; Renzi,G., Gazzetta Chimica Italiana, 1968, vol. 98, p. 667 - 680

  摘要：

  DOI：
• 作为产物：
  描述：

  3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以91%的产率得到4-乙酰基-5-甲基异恶唑-3-甲酸乙酯
  参考文献：
  名称：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate with 5,5-dimethyl-1,3-dioxanyl as a directing group

  摘要：

  Lateral lithiation of ethyl 4-acetyl-5-methyl-3-isoxazolyl carboxylate, a functionalized isoxazole AMPA analog, occurs cleanly at the C-5 methyl group with 5,5-dimethyl-1,3-dioxanyl as a directing group. The 4-acetyl isoxazole derivatives were transformed selectively by a modified Willgerodt-Kindler reaction into the corresponding homologated methyl esters after deprotection. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01782-1

文献信息

• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE
  申请人：METHYLGENE INC

  公开号：WO2005092899A1

  公开（公告）日：2005-10-06

  The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.

  这项发明涉及一系列对抑制组蛋白去乙酰化酶（HDAC）酶活性有用的化合物。该发明还提供了一种利用这些化合物抑制细胞中组蛋白去乙酰化酶的方法，以及一种利用这些HDAC抑制剂治疗细胞增殖性疾病和病况的方法。此外，该发明提供了包含这些HDAC抑制化合物和药用可接受载体的药物组合物。
• Lanthanide Catalyzed Synthesis of β-Hydroxyl Amides
  作者：P. Zhou、N. R. Natale

  DOI：10.1080/00397919808004440

  日期：1998.9

  Abstract Lanthanide (III) chloride improved the reaction of carboxylic esters with β-amino alkoxides (generated in situ from β-amino alcohols) and produced β-hydroxyl amides under mild conditions, and in high yields.

  摘要 镧系元素 (III) 氯化物改进了羧酸酯与 β-氨基醇盐（由 β-氨基醇原位生成）的反应，并在温和的条件下以高产率制备了 β-羟基酰胺。
• Base- and Copper-Catalysed Condensation of Primary Activated Nitro Compounds with Enolisable Compounds
  作者：Elena Trogu、Luca Cecchi、Francesco De Sarlo、Luca Guideri、Fabio Ponticelli、Fabrizio Machetti

  DOI：10.1002/ejoc.200900802

  日期：2009.12

  Primary nitro compounds have not been employed as nitrile oxide precursors in reactions with active methylene compounds because the reagents commonly used as dehydrating agents also react with these dipolarophiles. However, the CuII-catalysed cycloaddition/condensation procedure has been shown to be viable with these substrates, leading directly to the expected polyfunctional isoxazoles provided nitro

  在与活性亚甲基化合物的反应中，初级硝基化合物尚未用作氧化腈前体，因为通常用作脱水剂的试剂也与这些亲偶极体反应。然而，CuII 催化的环加成/缩合程序已被证明对这些底物是可行的，如果使用具有增强酸度（“活化”）的硝基化合物，则直接导致预期的多官能异恶唑。在不添加亲偶极体的情况下，这些硝基化合物会发生自缩合反应生成相应的呋喃。然而，与 3,4-二苯甲酰呋喃一样，苯甲酰硝基甲烷主要产生异构体 3-苯甲酰-4-硝基-5-苯基异恶唑，其结构已通过结晶分析证实。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Suzuki–Miyaura cross-coupling of benzylic bromides under microwave conditions
  作者：Steven W. McDaniel、Charles M. Keyari、Kevin C. Rider、Nicholas R. Natale、Philippe Diaz

  DOI：10.1016/j.tetlet.2011.08.096

  日期：2011.10

  A procedure for benzylic Suzuki–Miyaura cross-coupling under microwave conditions has been developed. These conditions allowed for heterocyclic compounds to be coupled. Optimum conditions found were Pd(OAc)2, JohnPhos as the catalyst and ligand, potassium carbonate as the base, and DMF as the solvent. Using these conditions, a library of structurally diverse compounds was synthesized.

  已经开发了一种在微波条件下用于苄基 Suzuki-Miyaura 交叉偶联的程序。这些条件允许杂环化合物偶联。发现的最佳条件是 Pd(OAc) 2，JohnPhos 作为催化剂和配体，碳酸钾作为碱，DMF 作为溶剂。使用这些条件，合成了结构多样的化合物库。
• A new direct synthesis of ACPA and novel AMPA analogues
  作者：David J Burkhart、Brendan Twamley、Nicholas R Natale

  DOI：10.1016/s0040-4039(01)01796-8

  日期：2001.11

  A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl3 as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2

  强大的谷氨酸神经递质激动剂（RS）-2-氨基-3-（3-羧基-5-甲基-4-异恶唑基）丙酸（ACPA）的新型合成方法可提供多种类似物作为神经系统疾病的候选药物。使用ErCl 3作为催化剂，成功地从醛4一锅合成α-氨基膦酸酯。具有（RS）-2-氨基-3-（3-羟基-5-甲基-4-异恶唑基）丙酸（AMPA）受体晶体结构的新型氨基膦酸的分子模型表明，这应该是一种有效的受体结合剂。