4,6-二甲基邻吡喃酮 | 480-65-9

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4,6-二甲基邻吡喃酮
• 中文别名: 4,6-二甲基香豆酸
• 英文名称: isodehydracetic acid
• 英文别名: isodehydroacetic acid；4,6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid；2,4-dimethyl-6-oxopyran-3-carboxylic acid
• CAS: 480-65-9
• 化学式: C₈H₈O₄
• mdl: MFCD00023864
• 分子量: 168.149
• InChiKey: QOADIMYPCZMZSG-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  219.79°C (rough estimate)
• 密度：
  1.1456 (rough estimate)
• 稳定性/保质期：
  避免与不相容材料接触，与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36
• 海关编码：
  2932209090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	Isodehydroacetic Acid 98% Material Safety Data Sheet
Synonym:	5-Carboxy-4,6-Dimethyl-2-Pyron
CAS:	480-65-9

Section 1 - Chemical Product MSDS Name:Isodehydroacetic Acid 98% Material Safety Data Sheet
Synonym:5-Carboxy-4,6-Dimethyl-2-Pyron

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
480-65-9	Isodehydroacetic Acid	98%	207-554-4

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.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.
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. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
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# 480-65-9: 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:
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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 154 - 156 deg C
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: C8H10O4
Molecular Weight: 170.0676

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 480-65-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Isodehydroacetic Acid - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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.
WGK (Water Danger/Protection)
CAS# 480-65-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 480-65-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 480-65-9 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：

  4,6-二甲基邻吡喃酮 在 4-二甲氨基吡啶 、 锰 、 (2,6-bis(pyrazol-1-yl)pyridine)NiBr₂ 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 2-methylbutyl-4,4-dimethyl-2-oxo-2H-pyran-5 carboxylate
  参考文献：
  名称：

  烷基吡啶鎓盐的脱氨还原甲基化

  摘要：

  甲基可以赋予有机分子有价值的特性，通常会增强生物活性。为了能够在简单的结构单元上和后期功能化中有效安装甲基，开发了仲卡特里茨基烷基吡啶鎓盐与碘甲烷的镍催化还原偶联。当与从烷基胺形成吡啶鎓盐结合时，该方法允许氨基容易地转化为具有广泛官能团和杂环耐受性的甲基。

  DOI：

  10.1021/acs.orglett.1c02458
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 4,6-二甲基邻吡喃酮
  参考文献：
  名称：

  Nieme; v. Pechmann, Justus Liebigs Annalen der Chemie, 1891, vol. 261, p. 202

  摘要：

  DOI：

文献信息

• An Improved Synthesis of a Mixture of Diethyl (<i>Z</i>)- and (<i>E</i>)-3-Methylglutaconates from Ethyl Acetoacetate
  作者：Kaleria I. Kuchkova、Alla B. Morari、Pavel F. Vlad

  DOI：10.1055/s-1993-35864

  日期：——

  A simple, efficient two-step synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from isodehydroacetic acid in 83 % yield is described. On the basis of this synthesis an improved procedure for the preparation of a mixture of (Z)- and (E)-3-methylglutaconic acids from ethyl acetoacetate in 44 % overall yield was elaborated.

  报道称，从异脱氢乙酸出发，以83%的产率简便高效地合成了二乙基（Z）-和（E）-3-甲基戊烯二酸酯的混合物。基于这一合成方法，改进了从乙酰乙酸乙酯制备（Z）-和（E）-3-甲基戊二酸的混合物的工艺，总产率为44%。
• Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
  作者：Kenji WATANABE、Takashi MIE、Akitami ICHIHARA、Hideaki OIKAWA、Mamoru HONMA

  DOI：10.1271/bbb.64.530

  日期：2000.1

  Macrophomate synthase, which we have recently purified, catalyzes an unusual multistep transformation from 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid). To investigate the substrate diversity of the enzyme, 40 analogs of 2-pyrone were prepared and their relative efficiency was examined in the enzymatic conversions. The experimental results reveal the structural requirements of the substrates and the rough size of the enzyme active site, and eliminate the ambiguity caused by contamination by other enzymes in the whole-cell experiments.

  我们最近纯化了一种名为黑腐醇合酶的酶，它催化一种不寻常的多步转化过程，从5-乙酰基-4-甲氧基-6-甲基-2-吡営转变为4-乙酰基-3-甲氧基-5-甲基苯甲酸（黑腐酸）。为了研究该酶的底物多样性，我们制备了40种2-吡喃酮的类似物，并考察了它们在酶促转化中的相对效率。实验结果揭示了底物的结构要求和酶活性位点的大致尺寸，并消除了全细胞实验中因其他酶污染导致的模糊性。
• Thienomethylpiperazine derivatives as inhibitors of soluble epoxide hydrolase
  申请人：SANOFI

  公开号：EP2881390A1

  公开（公告）日：2015-06-10

  The present invention relates to compounds of the formula I, wherein R1, R2, R3, R4 and X have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They are highly potent and selective soluble epoxide hydrolase inhibitors and are suitable, for example, for the therapy and prophylaxis of renal failure, diabetic nephropathy, type 2 diabetes mellitus, cardiovascular diseases, inflammatory diseases or could show beneficial effects in pain, dyslipidemia, atherosclerosis wound healing and stroke. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及式I的化合物，其中R1、R2、R3、R4和X的含义如索赔中所示。式I的化合物是有价值的药理活性化合物。它们是高效且选择性可溶性环氧化酶抑制剂，例如，适用于肾衰竭、糖尿病肾病、2型糖尿病、心血管疾病、炎症性疾病的治疗和预防，或者在疼痛、血脂异常、动脉粥样硬化、伤口愈合和中风方面可能显示有益效果。此外，该发明涉及制备式I化合物的方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• [EN] THIENOMETHYLPIPERAZINE DERIVATIVES AS INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE<br/>[FR] DÉRIVÉS THIÉNOMÉTHYLPIPÉRAZINE UTILISÉS COMME INHIBITEURS D'ÉPOXYDE HYDROLASE SOLUBLE
  申请人：SANOFI SA

  公开号：WO2015082474A1

  公开（公告）日：2015-06-11

  The present invention relates to compounds of the formula (I), wherein R1, R2, R3, R4 and X have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They are highly potent and selective soluble epoxide hydrolase inhibitors and are suitable, for example, for the therapy and prophylaxis of renal failure, diabetic nephropathy, type 2 diabetes mellitus, cardiovascular diseases, inflammatory diseases or could show beneficial effects in pain, dyslipidemia, atherosclerosis wound healing and stroke. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4和X具有权利要求中所指示的含义。式I的化合物是有价值的药理活性化合物。它们是高效且选择性可溶性环氧化酶抑制剂，例如适用于肾衰竭、糖尿病肾病、2型糖尿病、心血管疾病、炎症性疾病的治疗和预防，或者可能在疼痛、血脂异常、动脉粥样硬化、伤口愈合和中风中显示有益效果。此外，本发明还涉及制备式I化合物的方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• A simple and convenient synthesis of 3-arylpyran-2-ones via the Meerwein reaction
  作者：Roman Z. Lytvyn、Andriy O. Neshchadin、Khrystyna Ye. Pitkovych、Yuriy I. Horak、Juozas V. Grazulevicius、Tadeusz Lis、Vasyl Kinzhybalo、Mykola D. Obushak

  DOI：10.1016/j.tetlet.2015.11.076

  日期：2016.1

  A simple and practical procedure was proposed for the synthesis of 3-arylpyran-2-ones from the reaction of pyran-2-ones and arenediazonium chlorides under Meerwein reaction conditions.

  提出了一种简单而实用的方法，用于在Meerwein反应条件下由吡喃-2-酮与氯化壬二唑鎓的反应合成3-芳基吡喃-2-酮。