7-氧杂二环[4.1.0]庚烷-2-酮 | 6705-49-3

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: 7-氧杂二环[4.1.0]庚烷-2-酮
• 中文别名: 7-氧杂二环[4.1.0]-2-庚酮；2,3-环氧-1-环己酮
• 英文名称: 7-oxabicyclo[4.1.0]heptan-2-one
• 英文别名: 2,3-epoxycyclohexanone；2,3-epoxycyclohexan-1-one；2,3-epoxy-1-cyclohexanone；7-oxabicyclo[4.1.0]-heptane-2-one
• CAS: 6705-49-3
• 化学式: C₆H₈O₂
• mdl: MFCD00192371
• 分子量: 112.128
• InChiKey: QKOHEJBTNOEACF-UHFFFAOYSA-N

物化性质

• 沸点：
  76-78 °C15 mm Hg(lit.)
• 密度：
  1.13 g/mL at 25 °C(lit.)
• 闪点：
  205 °F
• 稳定性/保质期：
  1. 如果遵照规格使用和储存则不会分解，未有已知危险发生。
  2. 避免与强氧化剂接触。
  3. 存在于主流烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• WGK Germany：
  3
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方，并确保良好的通风。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 7-Oxabicyclo[4.1.0]heptan-2-one

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a dangerous substance according to GHS.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C6H8O2
Molecular Weight : 112,13 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
7-Oxabicyclo[4.1.0]heptan-2-one
6705-49-3 229-751-4 - - -

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Section 4. FIRST AID MEASURES
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Normal measures for preventive fire protection.
Conditions for safe storage
Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully
resealed and kept upright to prevent leakage. Store in cool place.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK (EU EN
14387) respirator cartridges. Use respirators and components tested and approved under appropriate
government standards such as NIOSH (US) or CEN (EU).
Hand protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without
touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves
after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Eye protection
Use equipment for eye protection tested and approved under appropriate government standards such as
NIOSH (US) or EN 166(EU).
Skin and body protection
impervious clothing, The type of protective equipment must be selected according to the concentration
and amount of the dangerous substance at the specific workplace.
Hygiene measures
General industrial hygiene practice.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Safety data
pH no data available
Melting point no data available
Boiling point 76 - 78 °C at 20 hPa - lit.
Flash point 96,00 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,13 g/mL at 25 °C
Water solubility no data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: no data available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  7-氧杂二环[4.1.0]庚烷-2-酮 在 一氧化碳 作用下， 以 四氢呋喃 、 水 为溶剂， 110.0 ℃ 、506.66 kPa 条件下， 反应 12.0h， 以99%的产率得到2-环己烯-1-酮
  参考文献：
  名称：

  水滑石负载金纳米粒子在水中催化CO在室温下进行环氧脱氧

  摘要：

  环氧脱氧：水滑石负载的金纳米粒子（Au / HT）在室温，CO和大气压下且无有机溶剂的情况下，有效地催化水中环氧的脱氧为烯烃。此外，Au / HT保留了其活性和选择性，可以重复使用。

  DOI：

  10.1002/chem.201001387
• 作为产物：
  描述：

  2-环己烯-1-酮 在 芘-1,6-二酮 、 氧气 、 sodium carbonate 、 异丙醇 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以91%的产率得到7-氧杂二环[4.1.0]庚烷-2-酮
  参考文献：
  名称：

  yr酮作为通用的光催化剂，可在可见光下原位生成过氧化氢进行氧化反应。

  摘要：

  吡咯二酮（PYDs）是用于三种氧化反应的有效光催化剂：缺电子烯烃的环氧化，有机硼的氧化羟基化以及在可见光照射下通过原位生成H 2 O 2，使用氧作为末端氧化剂和IPA作为硫化物的氧化溶剂和氢供体。

  DOI：

  10.1039/c9gc03152a

文献信息

• Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer
  作者：Xiaoshen Ma、Seth B. Herzon

  DOI：10.1021/acs.joc.6b01709

  日期：2016.10.7

  Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including

  已显示双（乙酰丙酮酸）钴介导氢原子转移到各种官能化烯烃中。所得烷基自由基中间体的原位氧化，然后水解，可方便地获得酮和酯。通过改性醇溶剂，可以获得不同的烷基酯产物。该方法与许多官能团兼容，包括链烯基卤化物，硫化物，三氟甲磺酸酯和膦酸酯，为乙烯基硅烷的Tamao-Fleming氧化和Arndt-Eistert同系物提供了温和而实用的替代方法。
• Mild and efficient CO-mediated eliminative deoxygenation of epoxides catalyzed by supported gold nanoparticles
  作者：Ji Ni、Lin He、Yong-Mei Liu、Yong Cao、He-Yong He、Kang-Nian Fan

  DOI：10.1039/c0cc02783a

  日期：——

  Supported gold nanoparticles (NPs), which are well-known epoxidation catalysts, were found to be exceptionally active for the selective deoxygenation of epoxides into alkenes using cheap and easily accessible CO and H(2)O as the reductant.

  发现负载的金纳米颗粒（NPs）是众所周知的环氧化催化剂，使用廉价且易于获得的CO和H（2）O作为还原剂，对于将环氧化物选择性脱氧成烯烃具有极高的活性。
• Effect of Ligand Fields on the Reactivity of O ₂ ‐Activating Iron(II)‐Benzilate Complexes of Neutral N5 Donor Ligands
  作者：Shrabanti Bhattacharya、Reena Singh、Tapan Kanti Paine

  DOI：10.1002/asia.202000142

  日期：2020.4.17

  Three new iron(II)-benzilate complexes [(N4Py)FeII (benzilate)]ClO4 (1), [(N4PyMe2 )FeII (benzilate)]ClO4 (2) and [(N4PyMe4 )FeII (benzilate)]ClO4 (3) of neutral pentadentate nitrogen donor ligands have been isolated and characterized to study their dioxygen reactivity. Single-crystal X-ray structures reveal a mononuclear six-coordinate iron(II) center in each case, where benzilate binds to the iron

  三种新的铁（II）-苯甲酸酯络合物[（N4Py）FeII（苯甲酸酯）] ClO4（1），[（N4PyMe2）FeII（苯甲酸酯）] （2）和[（N4PyMe4）FeII（苯甲酸酯）] （3）已分离出中性的五齿氮供体配体，并对其特征进行了研究以研究其双氧反应性。单晶X射线结构在每种情况下都显示一个单核六坐标铁（II）中心，其中苯甲酸酯通过一个羧酸氧以单齿模式结合到铁中心。与母体N4Py配体相比，在吡啶环的6位引入甲基使得N4PyMe2和N4PyMe4配体场更弱。所有的配合物（1-3）与双氧反应以将配位的苯甲酸酯定量地脱羧为二苯甲酮。对于位阻更强的配体的配合物，脱羧速度更快，并且遵循3> 2>的顺序 1.配合物显示出与硫代苯甲醚的氧原子转移反应性，并且还与含有弱CH键的底物发生氢原子转移反应。基于与外部底物的拦截研究，标记实验和Hammett分析，提出了一种亲核性铁（II）-氢
• Activation of H₂O₂ over Zr(IV). Insights from Model Studies on Zr-Monosubstituted Lindqvist Tungstates
  作者：Nataliya V. Maksimchuk、Vasilii Yu. Evtushok、Olga V. Zalomaeva、Gennadii M. Maksimov、Irina D. Ivanchikova、Yuriy A. Chesalov、Ilia V. Eltsov、Pavel A. Abramov、Tatyana S. Glazneva、Vadim V. Yanshole、Oxana A. Kholdeeva、R. John Errington、Albert Solé-Daura、Josep M. Poblet、Jorge J. Carbó

  DOI：10.1021/acscatal.1c02485

  日期：2021.8.20

  (Bu4N)2[W5O18Zr(H2O)3] (1) and (Bu4N)6[W5O18Zr(μ-OH)}2] (2), have been employed as molecular models to unravel the mechanism of hydrogen peroxide activation over Zr(IV) sites. Compounds 1 and 2 are hydrolytically stable and catalyze the epoxidation of C═C bonds in unfunctionalized alkenes and α,β-unsaturated ketones, as well as sulfoxidation of thioethers. Monomer 1 is more active than dimer 2. Acid

  Zr-单取代的 Lindqvist 型多金属氧酸盐 (Zr-POM)，(Bu 4 N) 2 [W 5 O 18 Zr(H 2 O) 3 ] ( 1 ) 和 (Bu 4 N) 6 [W 5 O 18 Zr( μ-OH)} 2 ] ( 2 )，已被用作分子模型来揭示过氧化氢在 Zr(IV) 位点上的活化机制。化合物1和2具有水解稳定性，可催化未官能化烯烃和 α,β-不饱和酮中 C=C 键的环氧化以及硫醚的磺化氧化。单体1比二聚体2更活跃。酸添加剂大大加速了氧化反应，并将氧化剂利用效率提高到>99%。产物分布表明异裂氧转移机制，该机制涉及在 Zr-POM 和 H 2 O 2相互作用时形成的亲电氧化物质。1和2与 H 2 O 2的相互作用以及由此产生的过氧衍生物已通过 UV-vis、FTIR、拉曼光谱、HR-ESI-MS 和组合 HPLC-ICP-原子发射光谱技术进行了研究。一个之间的相互作用17
• Nucleophilic versus Electrophilic Activation of Hydrogen Peroxide over Zr-Based Metal–Organic Frameworks
  作者：Olga V. Zalomaeva、Vasiliy Yu. Evtushok、Irina D. Ivanchikova、Tatyana S. Glazneva、Yuriy A. Chesalov、Kirill P. Larionov、Igor Y. Skobelev、Oxana A. Kholdeeva

  DOI：10.1021/acs.inorgchem.0c01084

  日期：2020.8.3

  acetonitrile solvent. Kinetic modeling on methyl phenyl sulfoxide oxidation coupled with adsorption studies supports a mechanism that involves the interaction of H2O2 with Zr sites with the formation of a nucleophilic oxidizing species and release of water followed by oxygen atom transfer from the nucleophilic oxidant to sulfoxide that competes with water for Zr sites. The nucleophilic peroxo species coexists

  基于Zr的金属有机框架（Zr-MOF）UiO-66和UiO-67在非质子溶剂中催化硫醚氧化，对相应的砜具有前所未有的高选择性（在大约50％的硫化物转化率下，只有1当量的H，96-99％）2 O 2）。已使用测试底物，动力学，吸附，同位素（18 O）标记和光谱学工具研究了反应机理。下列事实指出了过氧物种的优良亲核特征：（1）噻吩5-氧化物的氧化过程中亲核参数X Nu = 0.92，加入酸后其亲核参数X Nu = 0.92。（2）砜与亚砜之比为24的甲基苯亚砜与p竞争氧化-溴-甲基苯基硫醚；（3）相对于甲基苯基亚砜，甲基苯基硫醚氧化的初始速率明显降低（k S / k SO = 0.05）；（4）Hammett图的正斜率ρ＝ + 0.42，用于对位取代的芳基甲基亚砜的竞争性氧化。H 2 O 2在Zr-MOF上的亲核活化还通过其催化α，β-不饱和酮中缺电子的C═C键的环氧化以及乙腈溶剂的氧化来证明

表征谱图