4-羟基-2(5H)-呋喃酮 | 541-57-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 4-羟基-2(5H)-呋喃酮
• 中文别名: 季酮酸
• 英文名称: 4-hydroxy-2(5H)-furanone
• 英文别名: tetronic acid；4-hydroxyfuran-2(5H)-one；3-hydroxy-2H-furan-5-one
• CAS: 541-57-1
• 化学式: C₄H₄O₃
• mdl: MFCD00052187
• 分子量: 100.074
• InChiKey: JZQBAGOECGRTSA-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  316.03°C
• 密度：
  1.5510
• 溶解度：
  DMSO（少量）、甲醇（少量）
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解。避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存于阴凉、干燥、通风良好的库房。远离火种和热源，防止阳光直射，并确保包装密封。应与酸类及食用化学品分开存放，切忌混储。储区应备有合适的材料以处理可能的泄漏物。

SDS

Name:	4-Hydroxy-2(5h)-furanone 98% Material Safety Data Sheet
Synonym:	2,4-(3H,5H)-Furandione; beta-Tetronic aci
CAS:	541-57-1

Section 1 - Chemical Product MSDS Name:4-Hydroxy-2(5h)-furanone 98% Material Safety Data Sheet
Synonym:2,4-(3H,5H)-Furandione; beta-Tetronic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
541-57-1	4-Hydroxy-2(5H)-furanone, 98%	98%	208-785-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
Non-irritating to the skin.
Ingestion:
Low hazard for usual industrial handling.
Inhalation:
May cause respiratory tract irritation.
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 if irritation develops or persists. Flush skin with plenty of soap and water.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Avoid contact with skin and eyes.
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:
Good general ventilation should be sufficient to control airborne levels. Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.
Exposure Limits CAS# 541-57-1: 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: Solid
Color: light yellow-beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 142 - 143 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: soluble
Specific Gravity/Density:
Molecular Formula: C4H4O3
Molecular Weight: 100.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
None reported.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 541-57-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy-2(5H)-furanone, 98% - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 541-57-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 541-57-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 541-57-1 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

制备方法与用途

合成制备方法

暂无相关信息。

用途

暂无相关信息。

反应信息

• 作为反应物：
  描述：

  4-羟基-2(5H)-呋喃酮 在 草酰溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以83%的产率得到4-溴-2(5h)-呋喃酮
  参考文献：
  名称：

  分子内[2 + 2]光环加成反应合成氟代三环支架

  摘要：

  神话般的氟：在优化辐照条件后，通过[2 + 2]光环加成法合成氟化产物1和2是很容易的。缺电子的三氟烯烃单元在分子内与产物1反应（9个例子，dr> 95：5）。在侧链的位置2都被一个或两个氟取代基修饰后（例如，产生产物2），还对该反应进行了研究。

  DOI：

  10.1002/anie.201204080
• 作为产物：
  描述：

  乙酰基乙醇酸乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-羟基-2(5H)-呋喃酮
  参考文献：
  名称：

  一种季酮酸的合成工艺

  摘要：

  本发明提供了一种季酮酸的合成工艺。本发明是以廉价易得的羟基乙酸酯为起始前驱物，将其与乙酰卤进行反应，得到关键中间体2‑乙酰氧基乙酸酯，然后在碱性条件下进行迪克曼缩合，得到目标产物季酮酸。本发明的原料易得，反应条件温和，操作简便，合成成本低，便于大规模工业化生产。所得最终产物季酮酸纯度和收率高，收率可以达到93％以上。

  公开号：

  CN106008419B

文献信息

• Syntheses and antimicrobial activities of five-membered heterocycles having a phenylazo substituent.
  作者：KUNIYOSHI TANAKA、KEIZO MATSUO、AI NAKANISHI、MISAKO JO、HIRONORI SHIOTA、MIKIKO YAMAGUCHI、SAKIKO YOSHINO、KEIKO KAWAGUCHI

  DOI：10.1248/cpb.32.3291

  日期：——

  Several five-membered heterocycles having a phenylazo substituent, 3-phenylazotetronic acids (2a-n), 3-phenylazotetramic acids (4a-i), 4-phenylazo-5-isoxazolinones (6a-g, 8a-f) and 5-phenylazo-4-thiazolidinones (10a-f, 12a-e), were synthesized and tested for antimicrobial activities. Tetronic acid and tetramic acid derivatives (2 and 4) inhibited the growth of gram-positive bacteria. 5-Isoxazolinone and 4-thiazolidinone derivatives (8 and 10) showed inhibitory activities against fungi as well as bacteria.

  几种含有苯偶氮取代基的五元杂环化合物，即3-苯偶氮四嗪酸（2a-n）、3-苯偶氮四胺酸（4a-i）、4-苯偶氮-5-异恶唉酮（6a-g, 8a-f）和5-苯偶氮-4-噻唑烷酮（10a-f, 12a-e），被合成并测试了它们的抗菌活性。四嗪酸和四胺酸衍生物（2和4）抑制了革兰氏阳性细菌的生长。5-异恶唉酮和4-噻唑烷酮衍生物（8和10）不仅对细菌，而且对真菌也显示出抑制活性。
• A Synthetic Route to α-Substituted Butenolides: Enantioselective Synthesis of (+)-Ancepsenolide
  作者：Cynthia Ghobril、Jérémy Kister、Rachid Baati

  DOI：10.1002/ejoc.201100491

  日期：2011.7

  A variety of α-substituted butenolides was efficiently synthesized starting from commercially available tetronic acid and carboxylic acids in four steps. The effectiveness of this approach is illustrated in the short synthesis of one of the first butenolide acetogenins: (+)-ancepsenolide.

  从市售的特电子酸和羧酸开始，分四步有效地合成了各种 α-取代的丁烯内酯。这种方法的有效性在第一个丁烯内酯 acetogenins 之一的短合成中得到了说明：(+)-ancepsenolide。
• Synthesis of vulpinic and pulvinic acids from tetronic acid
  作者：Yann Bourdreux、Ewen Bodio、Catherine Willis、Célia Billaud、Thierry Le Gall、Charles Mioskowski

  DOI：10.1016/j.tet.2008.06.058

  日期：2008.9

  A common precursor, tetronic acid, was used in the synthesis of several vulpinic acids and pulvinic acids, which are pigments found in several lichens and mushrooms. The key features of this method are a two-step alkylidenation of benzyl tetronate and a Suzuki–Miyaura cross-coupling. The synthesis of several natural products, vulpinic acid, pinastric acid, xerocomic acid is described.

  常见的前体tetronic酸被用于合成几种硫化松香酸和pulvinic酸，这是在几种地衣和蘑菇中发现的颜料。该方法的关键特征是四甲基苄酯的两步烷基化和Suzuki-Miyaura交叉偶联。描述了几种天然产物的合成，如松果酸，松果酸，异黄酸。
• Free radical reactions for heterocycle synthesis. Part 7: 2-Bromobenzoic acids as building blocks in the construction of spirobenzolactones and spirobenzolactams
  作者：Wei Zhang、Georgia Pugh

  DOI：10.1016/s0040-4020(03)00655-0

  日期：2003.6

  A straightforward 2-step parallel synthesis for structurally diversified spiro compounds is developed. 2-Bromobenzoic acids are used as common building blocks to couple with a series of conjugated enoles or enamines. Sequential intramolecular free radical Michael additions lead to formation of spirobenzolactones, spirobenzolactams, spirobenzolactone-lactams, spiorbenzolactone-thiolactones, spiordilactones

  开发了一种简单的两步平行合成方法，用于结构上多样化的螺环化合物。2-溴苯甲酸用作常见的结构单元，与一系列共轭的烯醇或烯胺偶联。依次的分子内自由基迈克尔加成导致形成螺苯并内酯，螺苯并内酰胺，螺苯并内酯-内酰胺，螺苯并内酯-硫代内酯，螺二内酯和桥连螺内酯。
• Synthesis of novel potent cytotoxicy podophyllotoxin-naphthoquinone compounds via microwave-assited multicomponent domino reactions
  作者：Quynh Giang Nguyen Thi、Giang Le-Nhat-Thuy、Tuyet Anh Dang Thi、Phuong Hoang Thi、Anh Nguyen Tuan、Thu Ha Nguyen Thi、Thanh Tra Nguyen、Thanh Nguyen Ha、Ha Hoang Mai、Tuyen Van Nguyen

  DOI：10.1016/j.bmcl.2021.127841

  日期：2021.4

  A series of novel podophyllotoxin-naphthoquinone compounds 5a-p were synthesized in good yields using microwave-assisted four-component reactions of 2-hydroxy-1,4-naphthoquinone, aromatic benzaldehydes, tetronic acid and ammonium acetate. All the synthesized compounds were fully characterized by spectral data and evaluated for their cytotoxicity activities against KB, HepG2, Lu1, MCF7, and non-cancerous

  使用 2-羟基-1,4-萘醌、芳香族苯甲醛、丁酮酸和乙酸铵的微波辅助四组分反应，合成了一系列新型鬼臼毒素-萘醌化合物5a-p，收率良好。所有合成的化合物都通过光谱数据进行了充分表征，并评估了它们对 KB、HepG2、Lu1、MCF7 和非癌性 Hek-293 细胞系的细胞毒性活性。在筛选的 16 种新化合物中，化合物5a、5d、5h和5k显示出高效的抑制活性，IC 50 < 40 nM 对 HepG2 和 SK-Lu-1 细胞系，并且对非癌性 Hek-293 细胞系显示较低的毒性，证明这些化合物在开发潜在抗癌剂中的潜在重要性。

表征谱图