2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮 | 87769-39-9

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮
• 中文别名: 2,2,5,6-四甲基-4H-1,3-二氧杂-4-己酮
• 英文名称: 2,2,5,6-tetramethyl-1,3-dioxin-4-one
• 英文别名: 2,2,5,6-tetramethyl-4H-1,3-dioxin-4-one
• CAS: 87769-39-9
• 化学式: C₈H₁₂O₃
• mdl: MFCD00060139
• 分子量: 156.181
• InChiKey: NZEPEQVPVAXLSY-UHFFFAOYSA-N

物化性质

• 沸点：
  72°C 0,3mm
• 密度：
  1,07 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2932999099
• 储存条件：
  存储条件为0-10°C，并需置于惰性气体中，避免与空气接触和加热。

SDS

2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one Revision number: 5
SAFETY DATA SHEET

---

Section 1. IDENTIFICATION
Product name: 2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one

Revision number: 5

---

Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 4
Flammable liquids
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
None
Pictograms or hazard symbols
Signal word Warning
Combustible liquid
Hazard statements
Precautionary statements:
Keep away from flames and hot surfaces.
[Prevention]
Wear protective gloves and eye/face protection.
Store in a well-ventilated place. Keep cool.
[Storage]
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one
>95.0%(GC)
Percent:
CAS Number: 87769-39-9
Chemical Formula: C8H12O3

---

Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.
2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one

---

Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Unsuitable extinguishing Solid streams of water
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

---

Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Keep away from flames and hot surfaces. Take
measures to prevent the build up of electrostatic charge. Use explosion-proof
equipment. Wash hands and face thoroughly after handling.
Use a closed system, ventilation.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Comply with laws.
Packaging material:

---

Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Clear
Form:
Colour: Very pale yellow - Yellow
No data available
Odour:
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 72°C/0.4kPa
Flash point: No data available
2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 1.07
Solubility(ies):
[Water] No data available
No data available
[Other solvents]

---

Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Conditions to avoid: Open flame
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

---

Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

---

Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

---

Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

---

Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

---

Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
2,2,5,6-Tetramethyl-4H-1,3-dioxin-4-one

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮 以 乙醇 为溶剂， 以40%的产率得到2-甲基乙酰乙酸乙酯
  参考文献：
  名称：

  Sato, Masayuki; Ogasawara, Hiromichi; Takayama, Kazuhisa, Heterocycles, 1987, vol. 26, # 10, p. 2611 - 2614

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丙二酸亚异丙酯 在 吡啶 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮
  参考文献：
  名称：

  Sato, Masayuki; Ogasawara, Hiromichi; Oi, Keiichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1896 - 1901

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-甲基-3-氧代丁酸叔丁酯 在 4-乙酰氨基苯磺酰叠氮 、 2,2,5,6-四甲基-4H-1,3-二氧杂-4-酮 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以27%的产率得到t-butyl 2-diazopropanoate
  参考文献：
  名称：

  Ru（II）-Pheox催化的Si-H插入反应：对映体富集的碳和硅中心的构建

  摘要：

  我们建立了一个高度对映选择性的Si-H插入反应，使用Ru（II）-Pheox催化剂在碳和硅原子上构建了手性中心。[小α]-甲基-[小α]-重氮酯的催化不对称Si-H插入反应进行...

  DOI：

  10.1039/c7cc01070b

文献信息

• Chemoenzymatic Synthesis of Acyl Coenzyme A Substrates Enables <i>in Situ</i> Labeling of Small Molecules and Proteins
  作者：Vinayak Agarwal、Stefan Diethelm、Lauren Ray、Neha Garg、Takayoshi Awakawa、Pieter C. Dorrestein、Bradley S. Moore

  DOI：10.1021/acs.orglett.5b02113

  日期：2015.9.18

  generate fully functional acyl coenzyme A molecules that are then used as substrates to drive in situ acyl transfer reactions is described. Mass spectrometry based assays to verify the identity of acyl coenzyme A enzymatic products are also illustrated. The approach is responsive to a diverse array of carboxylic acids that can be elaborated to their corresponding coenzyme A thioesters, with potential applications

  描述了一种化学酶促方法，其产生全功能的酰基辅酶A分子，然后将其用作底物以驱动原位酰基转移反应。还说明了基于质谱的测定法，以验证酰基辅酶A酶产物的身份。该方法响应于可以修饰为其相应的辅酶A硫酯的各种羧酸，在利用酰基辅酶A底物的广泛化学生物学研究中具有潜在的应用前景。
• Sythesis of 1,3-dioxin-4-ones and their use in synthesis. XVIII. Synthesis of azetidin-2-ones from 1,3-dioxin-4-ones via 3-hydroxycarboxamides.
  作者：Jun-ichi SAKAKI、Satoshi KOBAYASHI、Masayuki SATO、Chikasra KANEKO

  DOI：10.1248/cpb.37.2952

  日期：——

  A general method for the synthesis of azetidin-2-ones from 1, 3-dioxin-4-ones is described. The method consists of 1) the formatin of β-ketocarboxamides, 2) their reduction to 3-hydroxycarboxamides, 3) mesylationg, and 4) base-mediated cyclization of 3-mesyloxycarboxamides to the final azetidinones. Stereochemical demand in the cyclizatino step has been clarified by using 5, 6-tri- and -tetramethylene derivatives of 2, 2-dimethyl-1, 3-dioxin-4-one. Microbiological reduction of the acetoacetamides by baker's yeast gave (S)-3-hydroxybutanamides of ≥98% optical purity, whose cyclization afforded (R)-4-methylazetidin-2-ones.

  描述了一种从1,3-二氧戊环-4-酮合成氮杂环丁-2-酮的一般方法。该方法包括：1）形成β-酮羧酰胺，2）将其还原为3-羟基羧酰胺，3）甲磺酰化，以及4）3-甲磺酰氧基羧酰胺在碱介导下环化，得到最终的氮杂环丁酮。通过使用2,2-二甲基-1,3-二氧戊环-4-酮的5,6-三甲基和四甲基衍生物，阐明了环化步骤中的立体化学需求。利用面包酵母对乙酰乙酰胺进行微生物还原，得到了光学纯度≥98%的(S)-3-羟基丁酰胺，其环化产物为(R)-4-甲基氮杂环丁-2-酮。
• Photochemical ring-contraction of fused bicyclic 4-pyrones: A novel 2-step cyclopentannulation approach
  作者：F.G. West、P.V. Fisher、G.U. Gunawardena、Scott Mitchell

  DOI：10.1016/s0040-4039(00)60630-5

  日期：1993.9

  Fused bicyclic 4-pyrones were prepared by condensation of enamines derived from cyclic ketones with diketene or substituted 1,3-dioxin-4-ones. Photolysis in a hydroxylic medium led to bicyclo[n3.0]alkenones bearing oxygenation at both angular positions. This process is occurs via regioselective nucleophilic solvent attack on the intermediate tricyclic oxyallyl zwitterion. The efficiency of the transformation

  稠合的双环4-吡喃酮是通过将环酮衍生的烯胺与双烯酮或取代的1,3-二恶英-4-酮缩合而制备的。在羟基介质中的光解导致双环[n3.0]烯酮在两个角位置均带有氧合。该过程是通过区域选择性亲核溶剂攻击中间的三环氧基烯丙基两性离子而发生的。发现转化效率取决于与4-吡喃酮稠合的环的大小。
• Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class
  作者：Hai-Hua Lu、Sergey V. Pronin、Yevgeniya Antonova-Koch、Stephan Meister、Elizabeth A. Winzeler、Ryan A. Shenvi

  DOI：10.1021/jacs.6b03899

  日期：2016.6.15

  marine metabolite with potent antimalarial activity, was synthesized as a single enantiomer in 13 steps from simple building blocks (17 linear steps). Chemical synthesis enabled identification of isocyanoterpene antiplasmodial activity against liver-stage parasites, which suggested that inhibition of heme detoxification does not exclusively underlie the mechanism of action of this class.

  7,20-Diisocyanoadociane 是一种稀有的海洋代谢物，具有强大的抗疟活性，它是由简单的结构单元（17 个线性步骤）通过 13 个步骤合成为单一对映异构体的。化学合成能够鉴定异氰萜烯抗疟原虫对肝期寄生虫的活性，这表明对血红素解毒的抑制并不完全是此类作用机制的基础。
• Synthesis of 1,3-dioxin-4-ones and their use in synthesis. Part XXIV. A novel synthesis of .BETA.-ketothioesters.
  作者：Jun-ichi SAKAKI、Satoshi KOBAYASHI、Masayuki SATO、Chikara KANEKO

  DOI：10.1248/cpb.38.2262

  日期：——

  A new general one-pot method for high-yield synthesis of S-alkyl β-ketothioesters by heating of 6-mono- and 5, 6-disubstituted 1, 3-dioxin-4-ones and thiols in an appropriate aprotic solvent is described. This procedure is available for large-scale preparation of a variety of β-ketothioesters.

  本文描述了一种新的通用一步法，通过在适当的无质子溶剂中加热6-单取代和5,6-双取代的1,3-二氧杂环-4-酮与硫醇，实现高产率合成S-烷基β-酮硫酯。该方法适用于大规模制备多种β-酮硫酯。

表征谱图