(S)-3-乙酰氧基-γ-丁内酯 | 191403-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (S)-3-乙酰氧基-γ-丁内酯
• 中文别名: (S)-3-乙酰氧基-Γ-丁内酯；(S)-3-乙酰氧基-gamma-丁内酯
• 英文名称: (3S)-β-acetoxy-γ-butyrolactone
• 英文别名: (S)-β-acetoxy-γ-butyrolactone；(S)-3-Acetoxy-gamma-butyrolactone；[(3S)-5-oxooxolan-3-yl] acetate
• CAS: 191403-65-3
• 化学式: C₆H₈O₄
• mdl: MFCD00672871
• 分子量: 144.127
• InChiKey: QOAAHMCFVNHTBI-YFKPBYRVSA-N

物化性质

• 沸点：
  182.71°C (rough estimate)
• 密度：
  1.1311 (rough estimate)
• 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)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S37/39
• 储存条件：
  存于阴凉干燥处

SDS

Name:	(S)-3-Acetoxy-gamma-Butyrolactone 95% Material Safety Data Sheet
Synonym:	None Known
CAS:	191403-65-3

Section 1 - Chemical Product MSDS Name:(S)-3-Acetoxy-gamma-Butyrolactone 95% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
191403-65-3	(S)-3-Acetoxy-gamma-butyrolactone	95%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Do NOT use mouth-to-mouth resuscitation.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 191403-65-3: 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: Liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
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: C6H8O4
Molecular Weight: 144.0536

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 191403-65-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-3-Acetoxy-gamma-butyrolactone - 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
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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 191403-65-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 191403-65-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 191403-65-3 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

• 作为产物：
  描述：

  (S)-3-乙酰氧基二氢-2,5-呋喃二酮 O-乙酰基-L-苹果酸酐 在 zinc(II) tetrahydroborate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以85%的产率得到(S)-3-乙酰氧基-γ-丁内酯
  参考文献：
  名称：

  Beta-substituted-gamma-butyrolactones and a process for preparation thereof

  摘要：

  本发明涉及一种制备(S)-或(R)-β-取代-γ-丁内酯或其混合物的过程。将β-取代-γ-琥珀酸酐通过锌硼氢化物在四氢呋喃、二氯甲烷和乙酸乙酯中选择的相容溶剂中转化为相应的β-取代-γ-丁内酯。获得的β-取代-γ-丁内酯晶体形式有用于制药、农药、香料和香精的生产。还公开了新型β-取代-γ-丁内酯。

  公开号：

  EP1398312A1

文献信息

• N-HETEROCYCLIC CARBENE-AMIDO PALLADIUM(II) CATALYSTS AND METHOD OF USE THEREOF
  申请人：Jung Kyung Woon

  公开号：US20100036131A1

  公开（公告）日：2010-02-11

  A new N-heterocyclic catalyst system which contains N-heterocyclic carbene and amido as ligands, which are strongly bound to a palladium metal. Another heteroatom functionality can be used as a third ligand L. The NHC-amidate ligand system is unique in structure, and shows excellent reactivities in a number of chemical reactions. The chemical reactions include carbon-carbon and carbon-heteroatom (oxygen and nitrogen) bond formations, and oxidation reactions of saturated carbon chemicals via C—H activation.

  一个新的N-杂环催化剂系统包含N-杂环卡宾和酰胺作为配体，它们与钯金属结合紧密。另一个杂原子功能基可以用作第三个配体L。NHC-酰胺配体系统在结构上独特，并在许多化学反应中显示出优异的反应性。这些化学反应包括碳-碳和碳-杂原子（氧和氮）键的形成，以及通过C—H活化对饱和碳化学物质的氧化反应。
• Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis – a novel transformation in carbohydrate chemistry
  作者：Markus Draskovits、Hubert Kalaus、Christian Stanetty、Marko D. Mihovilovic

  DOI：10.1039/c9cc05906g

  日期：——

  The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown

  据报道，N-杂环卡宾（NHC）催化醛糖的截留脱同位反应的发展。在还原糖的复杂情况下，可以利用NHC对醛的独特选择性。确定并机械理解了用于截留脱配或随后的氧化还原-内酯化的强底物治理的实例。更重要的是，已表明，催化剂的设计允许针对两种情况中的任何一种，调节具有结构上无偏的起始原料的反应的选择性。
• Process for the preparation of oxazolidinones and method of use thereof
  申请人：Hollingsworth I. Rawle

  公开号：US20070265451A1

  公开（公告）日：2007-11-15

  A process for preparing N-(substituted)-C-(substituted methyl)-oxazolidinones, C-(substituted methyl)-oxazolidinones, and N-(substituted)-C-(substituted methyl)-oxazolidinones, preferably chiral, from optically active C-(protected oxymethyl)-oxazolidinones is described. The process can be used to produce combinatorial libraries of the above substituted oxazolidinones in a two or three step reaction comprising a plurality of reagents differing in numbers of carbons or particular substituted oxazolidinones. A number of substituted oxazolidinones produced using the above process have been discovered to have antimicrobial activity.

  本文介绍了一种从光学活性的C-（保护的氧甲基）-噁唑烷酮制备N-（取代）-C-（取代甲基）-噁唑烷酮、C-（取代甲基）-噁唑烷酮和N-（取代）-C-（取代甲基）-噁唑烷酮的方法，其中优选手性化合物。该方法可用于在包含多种碳数或特定取代噁唑烷酮的多种试剂的两步或三步反应中产生上述取代噁唑烷酮的组合库。使用上述方法生产的许多取代噁唑烷酮已被发现具有抗微生物活性。
• PROCESS FOR THE PREPARATION OF OXAZOLIDINONES AND METHOD OF USE THEREOF
  申请人：Hollingsworth Rawle I.

  公开号：US20080146458A1

  公开（公告）日：2008-06-19

  Substituted oxazolidinone of the formula: wherein R 2 is alkyl selected from the group consisting of methyl, ethyl, and isopropyl moieties, are described. The compounds are antibacterial.

  描述了以下化学式的氧杂环丙酮类替代物：其中R2是选择自甲基，乙基和异丙基基团的烷基。这些化合物具有抗菌作用。
• Process for preparing optically pure (S)-3-hydroxy-gamma-butyrolactone
  申请人：Samsung Fine Chemicals Co., Ltd.

  公开号：US20020048796A1

  公开（公告）日：2002-04-25

  The present invention relates to a process for preparing optically pure (S)-3-hydroxy-&ggr;-butyrolactone expressed by the following Formula 1 and more particularly, to a process that enables preparing optically pure (S)-3-hydroxy-&ggr;-butyrolactone economically in large quantities, by: (a) Preparing &agr;-(1,4) linked oligosaccharide with adequate sugar distribution by reacting starch which is easily available from natural product with enzyme under a specific condition; and (b) Performing oxidation and cyclization sequentially under a specific condition. 1

  本发明涉及一种制备光学纯(S)-3-羟基-&ggr;-丁内酯的工艺，由下式 1 表示，更具体地说，涉及一种能够通过以下方法经济地大量制备光学纯(S)-3-羟基-&ggr;-丁内酯的工艺： (a) 通过在特定条件下使天然产物中容易获得的淀粉与酶反应，制备具有充分糖分 分布的&agr;-(1,4)连接寡糖；以及 (b) 在特定条件下依次进行氧化和环化反应。 1