4-溴-2(5h)-呋喃酮 | 56634-50-5

• 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-溴-2(5h)-呋喃酮
• 英文名称: 4-bromo-5H-furan-2-one
• 英文别名: 4-bromofuran-2(5H)-one；4-bromo-2(5H)-furanone；4-bromofuran-2-one；β-tetronic acid bromide；3-bromo-2H-furan-5-one
• CAS: 56634-50-5
• 化学式: C₄H₃BrO₂
• 分子量: 162.971
• InChiKey: GQSKFTFPHAXZSA-UHFFFAOYSA-N

物化性质

• 熔点：
  77 °C
• 沸点：
  274.3±33.0 °C(Predicted)
• 密度：
  1.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090
• 储存条件：
  2-8°C，惰性气氛

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Bromofuran-2-one
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromofuran-2-one
CAS number: 56634-50-5

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H3BrO2
Molecular weight: 163

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴-2(5h)-呋喃酮 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到4-azido-5H-furan-2-one
  参考文献：
  名称：

  4-Azidotetronic Acids: A New Class of Azido Derivatives

  摘要：

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.

  DOI：

  10.1080/00397910008087364
• 作为产物：
  描述：

  4-(tributylstannyl)furan-2(5H)-one 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到4-溴-2(5h)-呋喃酮
  参考文献：
  名称：

  Reactions of Stannylfuranones: Facile Preparation of 4-Halo-2(5H)-furanones

  摘要：

  4-Halo-2(SH)-furanones are readily prepared from 4-tributylstannyl-2(SH)-furanone.

  DOI：

  10.1080/00397919408011296

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150322063A1

  公开（公告）日：2015-11-12

  A compound represented by Formula [1] (in the formula, Z 1 represents N, CH, or the like; X 1 represents NH or the like; R 1 represents a heteroaryl group or the like; each of R 2 , R 3 , and R 4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R 5 represents a heteroaryl group or the like) or salt thereof.

  由式[1]表示的化合物（在该式中，Z表示N、CH或类似物；X表示NH或类似物；R表示杂环烷基或类似物；R2、R3和R4中的每一个表示氢原子、卤原子、烷氧基或类似物；R5表示杂环烷基或类似物）或其盐。
• Enantioselective Total Synthesis of Cannogenol-3-<i>O</i>-α-<scp>l</scp>-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions
  作者：Bijay Bhattarai、Pavel Nagorny

  DOI：10.1021/acs.orglett.7b03513

  日期：2018.1.5

  A concise and scalable enantioselective total synthesis of the natural cardenolides cannogenol and cannogenol-3-O-α-l-rhamnoside has been achieved in 18 linear steps. The synthesis features a Cu(II)-catalyzed enantioselective and diastereoselective Michael reaction/tandem aldol cyclization and a one-pot reduction/transposition, which resulted in a rapid (6 linear steps) assembly of a functionalized

  简明和天然卡烯内酯的对映选择性可伸缩总合成cannogenol和cannogenol -3- ö -α-升-rhamnoside已在18个线性步骤来实现。该合成具有Cu（II）催化的对映选择性和非对映选择性Michael反应/串联醛醇缩合环化和一锅还原/易位，可快速（6线性步骤）组装含C19氧合的功能化中间体到去烯醇内啡醇。此外，对于在合成cannogenol的C3位实现区域选择性和立体选择性糖基化策略开发和应用的制备cannogenol -3- ö -α-升-rhamnoside。
• [EN] INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL<br/>[FR] INHIBITEURS DU CANAL POTASSIQUE MÉDULLAIRE EXTERNE RÉNAL
  申请人：MERCK SHARP & DOHME

  公开号：WO2015100147A1

  公开（公告）日：2015-07-02

  Novel spirocyclic compounds of formula I: and pharmaceutically acceptable salts thereof are disclosed as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention. Pharmaceutical compositions and methods of treatment are also included.

  公开了公式I的新型螺环化合物及其药学上可接受的盐，作为ROMK（Kir1.1）通道的抑制剂。这些化合物可用作利尿剂和/或钠利尿剂，并用于治疗和预防包括高血压、心力衰竭和慢性肾脏疾病在内的心血管疾病以及与过多盐分和水分潴留有关的疾病。还包括药物组合物和治疗方法。
• [EN] INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL<br/>[FR] INHIBITEURS DU CANAL POTASSIQUE MÉDULLAIRE EXTERNE RÉNAL
  申请人：MERCK SHARP & DOHME

  公开号：WO2016127358A1

  公开（公告）日：2016-08-18

  Disclosed are compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

  公开的是Formula I的化合物及其药学上可接受的盐，这些化合物是ROMK (Kir1.1)通道的抑制剂。这些化合物可用作利尿剂和/或钠利尿剂，并用于治疗和预防包括高血压、心力衰竭和慢性肾脏疾病在内的心血管疾病以及与过多盐分和水分潴留有关的疾病。
• Diverted total synthesis of melodorinol analogues and evaluation of their cytotoxicity
  作者：Tanatorn Khotavivattana、Thitiphong Khamkhenshorngphanuch、Kitiya Rassamee、Pongpun Siripong、Tirayut Vilaivan

  DOI：10.1016/j.tetlet.2018.06.005

  日期：2018.7

  melodorinol analogues were synthesized via a diverted total synthesis approach, leading to structural modifications on several regions of the molecule. Their cytotoxicity was evaluated against five human cancer cell lines (KB, HeLa-S3, MCF-7, HT-29 and A549). Structure-activity relationship studies revealed key parameters that affect the cytotoxicity. In particular, the novel 4-bromo-furanone analogues exhibited

  通过合成了一系列的melodorinol类似物一种转移的全合成方法，导致分子几个区域的结构修饰。评估了它们对五种人类癌细胞系（KB，HeLa-S3，MCF-7，HT-29和A549）的细胞毒性。结构-活性关系研究揭示了影响细胞毒性的关键参数。特别地，与相应的非溴代类似物相比，新型4-溴呋喃酮类似物表现出更大的细胞毒性。C-6的立体化学以及C-6和C-7羟基上的酰基取代基的性质也起着重要的作用。最有效的类似物显示出对KB和HeLa-S3的细胞毒性比美洛瑞诺高约15倍，并且对MCF-7，HT-29和A549细胞系也显示出极高的效能。