5-氯-2-糠酸 | 618-30-4

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 5-氯-2-糠酸
• 中文别名: 5-氯呋喃-2-甲酸；5-氯-2-呋喃羧酸
• 英文名称: 5-chlorofuran-2-carboxylic acid
• 英文别名: 5-chloro-2-furoic acid；5-chlorofuroic acid；5-Chlor-furan-2-carbonsaeure；5-Chlor-2-furancarbonsaeure；5-chloro-2-furancarboxylic acid
• CAS: 618-30-4
• 化学式: C₅H₃ClO₃
• mdl: MFCD00093272
• 分子量: 146.53
• InChiKey: NNTBDUTXMIMRKK-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C
• 沸点：
  246.8±20.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 海关编码：
  2932190090
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-2-furoic acid
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Chloro-2-furoic acid
CAS number: 618-30-4

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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.

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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.

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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.

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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:

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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.

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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: C5H3ClO3
Molecular weight: 146.5

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

5-氯-2-糠酸是羧酸类衍生物，可用作医药中间体。

制备

5-氯-2-糠酸可以通过两种方法制取：一是以5-氯-2-呋喃甲醛为原料进行氧化反应；二是通过坎尼扎罗反应（Cannizzaro reaction）完成。具体而言，由5-氯-2-糖醛经空气氧化可制得，此过程在45℃、强烈搅拌的条件下进行。将反应物过滤回收催化剂氧化铜后，滤液用硫酸酸化至pH值为3-2.5，随后吸滤、水洗、烘干即可得到糠酸。

另一种制备方法是，在中性或碱性介质中，使用次氯酸钠或高锰酸钾对5-氯-2-糠醛进行氧化反应约2小时，然后用盐酸酸化。此法的收率可达98%左右。

反应信息

• 作为反应物：
  描述：

  5-氯-2-糠酸 在 Pd-BaSO₄ 、 氯化亚砜 、 xylene 、 苯 作用下， 生成 5-氯-2-糠醛
  参考文献：
  名称：

  Okuzumi, Nippon Kagaku Zasshi, 1958, vol. 79, p. 1366,1369

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-2-糠醛 在 NADH oxidase and vanillin dehydrogenase 1 co-expressed in Escherichia coli cells 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以99%的产率得到5-氯-2-糠酸
  参考文献：
  名称：

  辅因子设计的全细胞生物催化剂可高效生产呋喃羧酸

  摘要：

  呋喃羧酸是各种工业中有用的化学物质。在这项工作中，据报道，辅因子工程化的大肠杆菌细胞具有高生产率的生物催化生产呋喃羧酸。将NADH氧化酶（NOX）引入具有醛脱氢酶（ALDHs）的大肠杆菌中，以促进细胞内NAD +再生，从而显着增强ALDH催化的氧化作用。这些工程化的生物催化剂能够有效地好氧氧化各种芳香醛。更重要的是，它们显示出对有毒呋喃的高底物耐受性。大肠杆菌共表达香草醛脱氢酶和NOX（E. coli_CtVDH1_NOX）可以将250 mM的5-羟甲基糠醛（HMF）有效氧化为5-羟甲基-2-呋喃甲酸（HMFCA），生产率为3.7 g / L h。使用E. coli_ CtVDH2_NOX作为催化剂，可以平滑地氧化多达240 mM的糠醛和5-甲氧基甲基糠醛（MMF）。分批进料合成生产了2-呋喃甲酸（FCA，227 mM）和5-甲氧基甲基-2-呋喃甲酸（MMFCA，287 mM），分别提供了2

  DOI：

  10.1002/cctc.202000259
• 作为试剂：
  描述：

  2-BOC-八氢吡咯基[3,4-C]吡咯 、 5-氯-2-糠酸 在 5-氯-2-糠酸 作用下， 以60的产率得到Tert-butyl 5-(5-chlorofuran-2-carbonyl)-octahydropyrrolo[3,4-c]pyrrole-2-carboxylate
  参考文献：
  名称：

  Nicotinic acetylcholine receptor sub-type selective amides of diazabicycloalkanes

  摘要：

  本发明涉及化合物、包括该化合物的制药组合物以及其制备和使用方法。该化合物是酰胺化合物，可以由某些杂环羧酸和某些二氮杂双环烷制备而成。该化合物对中枢神经系统（CNS）中的α4β2亚型神经尼古丁受体具有选择性和高亲和力。该化合物和组合物可用于治疗和/或预防各种疾病或疾病，特别是CNS疾病。该化合物可以：（i）改变患者大脑尼古丁胆碱受体的数量，（ii）表现出神经保护作用，以及（iii）在有效剂量下，不会产生明显的不良副作用（例如显著增加血压和心率、对胃肠道产生显著负面影响以及对骨骼肌产生显著影响等副作用）。

  公开号：

  US09580434B2

文献信息

• [EN] COMBINATION PHARMACEUTICAL AGENTS AS RSV INHIBITORS<br/>[FR] AGENTS PHARMACEUTIQUES EN COMBINAISON EN TANT QU'INHIBITEURS DE RSV
  申请人：ENANTA PHARM INC

  公开号：WO2019067864A1

  公开（公告）日：2019-04-04

  The present invention relates to pharmaceutical agents administered to a subject either in combination or in series for the treatment of a Respiratory Syncytial Virus (RSV) infection, wherein treatment comprises administering a compound effective to inhibit the function of the RSV and an additional compound or combinations of compounds having anti-RSV activity.

  本发明涉及用于治疗呼吸道合胞病毒（RSV）感染的药物剂，该药物剂可以单独或连续给予受试者，治疗包括给予一种有效抑制RSV功能的化合物以及具有抗RSV活性的另一种化合物或化合物组合。
• Electrochemical Oxidation Enables Regioselective and Scalable α-C(sp³)-H Acyloxylation of Sulfides
  作者：Huamin Wang、Meng He、Yongli Li、Heng Zhang、Dali Yang、Masanari Nagasaka、Zongchao Lv、Zhipeng Guan、Yangmin Cao、Fengping Gong、Zhilin Zhou、Jingyun Zhu、Supravat Samanta、Abhishek Dutta Chowdhury、Aiwen Lei

  DOI：10.1021/jacs.1c00288

  日期：2021.3.10

  A highly selective, environmentally friendly, and scalable electrochemical protocol for the construction of α-acyloxy sulfides, through the synergistic effect of self-assembly-induced C(sp3)–H/O–H cross-coupling, is reported. It features exceptionally broad substrate scope, high regioselectivity, gram-scale synthesis, construction of complex molecules, and applicability to a variety of nucleophiles

  报道了一种通过自组装诱导的 C(sp 3 )-H/O-H 交叉偶联的协同效应构建 α-酰氧基硫化物的高选择性、环境友好和可扩展的电化学方案。它具有极其广泛的底物范围、高区域选择性、克级合成、复杂分子的构建以及对各种亲核试剂的适用性。此外，软X射线吸收技术和一系列控制实验已被用来证明基板自组装的关键作用，这确实是我们电化学方案中高区域选择性的出色兼容性和精确控制的原因.
• Synthesis and evaluation of 2‐(4‐[4‐acetylpiperazine‐1‐carbonyl] phenyl)‐ <scp>1H</scp> ‐benzo[d]imidazole‐4‐carboxamide derivatives as potential <scp>PARP</scp> ‐1 inhibitors and preliminary study on structure‐activity relationship
  作者：Miaojia Chen、Honglin Huang、Kaiyue Wu、Yunfan Liu、Lizhi Jiang、Yang Li、Guotao Tang、Junmei Peng、Xuan Cao

  DOI：10.1002/ddr.21843

  日期：2022.2

  Here in, a series of 2-(4-[4-acetylpiperazine-1-carbonyl]phenyl)-1H-benzo[d]imidazole-4-carboxamide derivatives have been designed, synthesized, and successful characterization as novel and effective poly ADP-ribose polymerases (PARP)-1 inhibitors to improve the structure–activity relationships about the substituents in the hydrophobic pocket. These derivatives were evaluated for their PARP-1 inhibitory

  尽管对 1H-苯并[d]咪唑-4-甲酰胺衍生物的探索已经很长时间，但疏水袋（AD 结合位点）中取代基的构效关系尚未彻底发现。在这里，设计、合成了一系列 2-(4-[4-乙酰基哌嗪-1-羰基]苯基)-1H-苯并[d]咪唑-4-甲酰胺衍生物，并成功表征为新型有效的聚 ADP -核糖聚合酶（PARP）-1抑制剂，以改善疏水袋中取代基的结构-活性关系。使用 PARP 试剂盒测定法和 MTT 方法评估这些衍生物的 PARP-1 抑制活性和对 BRCA-1 缺陷细胞 (MDA-MB-436) 和野生细胞 (MCF-7) 的细胞抑制作用。结果表明，与其他杂环化合物相比，14n-14q表现出更好的 PARP-1 抑制活性。在这些衍生物中，化合物14p对 PARP-1 酶的抑制作用最强（IC 50  = 0.023 μM），与奥拉帕尼接近。14p (IC 50  = 43.56 ± 0.69 μM) 和14q
• [EN] BENZODIAZEPINE DERIVATIVES AS RSV INHIBITORS<br/>[FR] DÉRIVÉS BENZODIAZÉPINE UTILISÉS COMME INHIBITEURS DU VIRUS RESPIRATOIRE SYNCYTIAL (RSV)
  申请人：ENANTA PHARM INC

  公开号：WO2017015449A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了化合物的结构式（I），或其药学上可接受的盐、酯或前药：这些化合物抑制呼吸道合胞病毒（RSV）。本发明还涉及包含上述化合物的药物组合物，用于治疗患有RSV感染的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的RSV感染的方法。
• [EN] THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION<br/>[FR] COMPOSÉS THÉRAPEUTIQUES ET MÉTHODES POUR TRAITER UNE INFECTION
  申请人：UNIV RUTGERS

  公开号：WO2019099402A1

  公开（公告）日：2019-05-23

  Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

  本文披露了化合物的结构式（I）或其盐，以及包含表现出抗菌活性的化合物的组合物的组合物，当单独测试和/或与细菌外排泵抑制剂结合时。还披露了治疗或预防动物细菌感染的方法，包括向动物单独或与细菌外排泵抑制剂的给药结合给动物的结构式（I）的化合物。

表征谱图