4,6-二甲基阔马酸甲酯 | 41264-06-6

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4,6-二甲基阔马酸甲酯
• 中文别名: 5-甲氧羰基-4,6-二甲基-2-吡喃酮；4,6-二甲基-2-氧-2H-吡喃-5-甲酸甲酯
• 英文名称: methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate
• 英文别名: methyl 2,4-dimethyl-6-oxopyran-3-carboxylate
• CAS: 41264-06-6
• 化学式: C₉H₁₀O₄
• mdl: MFCD00006642
• 分子量: 182.176
• InChiKey: VLYBFLKIZIACQH-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C(lit.)
• 沸点：
  167 °C14 mm Hg(lit.)
• 密度：
  1.1634 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  DryPowder
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2932209090
• 安全说明：
  S24/25
• 储存条件：
  应存放在阴凉干燥处。

SDS

Name:	Methyl Isodehydracetate 97% Material Safety Data Sheet
Synonym:	Methyl-4,6-Dimethyl-2-Oxo-2H-Pyran-5-Carboxylate
CAS:	41264-06-6

Section 1 - Chemical Product MSDS Name:Methyl Isodehydracetate 97% Material Safety Data Sheet
Synonym:Methyl-4,6-Dimethyl-2-Oxo-2H-Pyran-5-Carboxylate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
41264-06-6	Methyl Isodehydracetate	97%	255-283-5

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.
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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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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. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
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.

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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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 41264-06-6: 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 minimize contact with skin.
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: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 167 deg C @ 14.00mm Hg
Freezing/Melting Point: 67.00 - 69.00 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: C9H10O4
Molecular Weight: 182.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing 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# 41264-06-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl Isodehydracetate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 41264-06-6: No information available.
Canada
CAS# 41264-06-6 is listed on Canada's NDSL List.
CAS# 41264-06-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 41264-06-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述：4,6-二甲基阔马酸甲酯可用作医药合成中间体。若吸入该物质，请将患者移至空气新鲜处；如皮肤接触，应脱去污染衣物，并用肥皂水和清水彻底冲洗皮肤；如有不适，请就医；如眼睛接触到该物质，应翻开眼睑，用流动清水或生理盐水冲洗，并立即就医；如误食，请立即漱口，禁止催吐，并及时就医。

反应信息

• 作为反应物：
  描述：

  4,6-二甲基阔马酸甲酯 在 硫酸 作用下， 反应 120.0h， 以92%的产率得到4,6-二甲基邻吡喃酮
  参考文献：
  名称：

  Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates

  摘要：

  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。

  DOI：

  10.1271/bbb.64.530
• 作为产物：
  描述：

  4,6-二甲基邻吡喃酮 在 氯化亚砜 作用下， 生成 4,6-二甲基阔马酸甲酯
  参考文献：
  名称：

  Alkyl Esters of Isodehydroacetic Acid

  摘要：

  DOI：

  10.1021/ja01097a518

文献信息

• Upgrading malic acid to bio-based benzoates via a Diels–Alder-initiated sequence with the methyl coumalate platform
  作者：Jennifer J. Lee、Gerald R. Pollock III、Donald Mitchell、Lindsay Kasuga、George A. Kraus

  DOI：10.1039/c4ra07105k

  日期：——

  Malic acid dimerization was optimized to methyl coumalate from which a Diels–Alder strategy produced a variety of bio-based benzoates.

  苹果酸二聚体化学反应被优化为从中制备甲基香豆酸酯，通过迪尔斯-阿尔德反应策略产生各种生物基苯甲酸酯。
• Application of 1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes in Diels-Alder Reactions: Synthesis of<i>ortho</i>-CF₂Br-Substituted Biaryls
  作者：Valentine Nenajdenko、Günter Haufe、Vasiliy Muzalevskiy、Aleksey Shastin、Elizabeth Balenkova

  DOI：10.1055/s-2008-1067221

  日期：2008.9

  1-(3-Bromo-3,3-difluoroprop-1 1-ynyl)benzenes were found to be good dienophiles in Diels-Alder reactions. Based on this key reaction a new pathway towards biaryls with an ortho-CF 2 Br group was elaborated.

  1-(3-Bromo-3,3-difluoroprop-1 1-ynyl)苯被发现是Diels-Alder反应中良好的亲双烯体。基于这一关键反应，我们详细阐述了获得具有邻位-CF 2 Br 基团的联芳基化合物的新途径。
• 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。
• Pyridone derivatives as NK3 antagonists
  申请人：Khanzhin Nikolay

  公开号：US20110144164A1

  公开（公告）日：2011-06-16

  The present invention relates to compounds useful in therapy, in particular in the treatment of psychosis, to compositions comprising said compounds, and to methods of treating diseases comprising the administration of said compounds.

  本发明涉及在治疗中有用的化合物，特别是在治疗精神病方面，涉及包含该化合物的组合物，以及包括给予该化合物的治疗方法。
• [EN] PYRIDONE DERIVATIVES AS NK3 ANTAGONISTS<br/>[FR] DÉRIVÉS DE PYRIDONE ANTAGONISTES DE NK3
  申请人：LUNDBECK & CO AS H

  公开号：WO2011072691A1

  公开（公告）日：2011-06-23

  The present invention relates to compound of formula (I) useful in therapy, in particular in the treatment of psychosis, to compositions comprising said compounds, and to methods of treating diseases comprising the administration of said compounds.

  本发明涉及一种具有式（I）的化合物，用于治疗，特别是在治疗精神病方面，包括所述化合物的组合物，以及通过给予该化合物来治疗疾病的方法。