4-(5-甲酰基-2-呋喃基)苯甲酸甲酯 | 53355-29-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(5-甲酰基-2-呋喃基)苯甲酸甲酯
• 中文别名: 4-(5-甲酰基呋喃-2-基)苯甲到甲酯
• 英文名称: methyl 4-(5-formylfuran-2-yl)benzoate
• CAS: 53355-29-6
• 化学式: C₁₃H₁₀O₄
• mdl: MFCD00439546
• 分子量: 230.22
• InChiKey: JHCPIIVQUDGETN-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  394.7±37.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932190090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-(5-formylfuran-2-yl)benzoate
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: Methyl 4-(5-formylfuran-2-yl)benzoate
CAS number: 53355-29-6

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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: C13H10O4
Molecular weight: 230.2

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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.

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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

反应信息

• 作为反应物：
  描述：

  4-(5-甲酰基-2-呋喃基)苯甲酸甲酯 在 lithium hydroxide monohydrate 、 水 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.1h， 生成 sortin1
  参考文献：
  名称：

  Synthesis of alkyne-tagged and biotin-tagged Sortin1 as novel photoaffinity probes

  摘要：

  Sortin1 is an inhibitor of vesicular biogenesis and transport, which is shared among eukaryotes and plants with an unknown mode of action. Toward exploration of its target proteins, we developed alkyne as well as biotin conjugated photoaffinity probes derived from Sortin1. Due to the presence of phenylketone moiety, Sortin1 was anticipated to serve as a photoreactive group in a similar manner to a commonly used photoreactive group, benzophenone. The core structure based on 5-oxo-1,4-dihydroindenopyridine was constructed in one step using three-component Hantzsch dihydropyridine synthesis. We demonstrated that Sortin1 displayed photocrosslinking reactivity against a model binding protein, which would be useful for capturing and detecting binding proteins. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.060
• 作为产物：
  描述：

  2-糠醛缩二乙醇 在 palladium on activated charcoal 正丁基锂 、 三乙胺 作用下， 以 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-(5-甲酰基-2-呋喃基)苯甲酸甲酯
  参考文献：
  名称：

  A Practical One-Pot Synthesis of 5-Aryl-2-furaldehydes

  摘要：

  描述了一种有用的一锅法合成5-芳基-2-呋喃醛的方法，该方法通过钯介导的铃木偶联反应将芳基卤化物与原位生成的5-(二乙氧基甲基)-2-呋喃硼酸结合。该程序具有广泛的适用性，能够提供高产率，并且易于放大。

  DOI：

  10.1055/s-2001-16759

文献信息

• Common ligand mimics: benzimidazoles
  申请人：——

  公开号：US20030104473A1

  公开（公告）日：2003-06-05

  The present invention provides common ligand mimics that act as common ligands for a receptor family. The present invention also provides bi-ligands containing these common ligand mimics. Bi-ligands of the invention provide enhanced affinity and/or selectivity of ligand binding to a receptor or receptor family through the synergistic action of the common ligand mimic and specificity ligand that compose the bi-ligand. The present invention also provides combinatorial libraries containing the common ligand mimics and bi-ligands of the invention. Further, the present invention provides methods for manufacturing the common ligand mimics and bi-ligands of the invention and methods for assaying the combinatorial libraries of the invention.

  本发明提供了作为受体家族的共同配体的共同配体模拟物。本发明还提供了含有这些共同配体模拟物的双配体。本发明的双配体通过共同配体模拟物和构成双配体的特异性配体的协同作用，提供了对受体或受体家族的配体结合的增强亲和力和/或选择性。本发明还提供了含有本发明的共同配体模拟物和双配体的组合库。此外，本发明提供了制造本发明的共同配体模拟物和双配体的方法，以及检测本发明的组合库的方法。
• Synthesis and biological evaluation of novel rhodanine-based structures with antiviral activity towards HHV-6 virus
  作者：Valentina Gentili、Giulia Turrin、Paolo Marchetti、Sabrina Rizzo、Giovanna Schiuma、Silvia Beltrami、Virginia Cristofori、Davide Illuminati、Greta Compagnin、Claudio Trapella、Roberta Rizzo、Daria Bortolotti、Anna Fantinati

  DOI：10.1016/j.bioorg.2021.105518

  日期：2022.2

  of anti-HHV6 compounds provides a valuable opportunity for developing efficient antiviral therapies. A possible target for antiviral drugs is the virus-cell fusion step. In this study, we synthetized potential fusion intermediates inhibitors based on the rhodanine structure. The obtained derivatives were tested for cytotoxicity and for antiviral activity in human cells infected with HHV6. Level of infection

  对与人类疱疹病毒 6 (HHV-6) 感染或再激活相关的疾病的认识提高，导致人们对评估可用于 HHV-6 疾病临床管理的最佳治疗方案的兴趣日益浓厚。然而，尚未批准专门用于 HHV-6 感染治疗的化合物。出于这个原因，抗 HHV6 化合物的鉴定为开发有效的抗病毒疗法提供了宝贵的机会。抗病毒药物的一个可能目标是病毒-细胞融合步骤。在这项研究中，我们合成了基于罗丹宁结构的潜在融合中间体抑制剂。测试了获得的衍生物在感染 HHV6 的人类细胞中的细胞毒性和抗病毒活性。在感染后长达 7 天的不同时间点通过病毒 DNA 定量监测感染水平。在合成衍生物中，图9e显示对病毒复制的显着抑制作用持续超过7天，这可能归因于罗丹宁部分的亲水性和疏水性取代基的特定组合。我们的结果支持使用这些两亲性融合抑制剂治疗 HHV-6 感染。
• Non-thiol farnesyltransferase inhibitors: N-(4-tolylacetylamino-3-benzoylphenyl)-3-arylfurylacrylic acid amides
  作者：Andreas Mitsch、Pia Wißner、Katrin Silber、Peter Haebel、Isabel Sattler、Gerhard Klebe、Martin Schlitzer

  DOI：10.1016/j.bmc.2004.07.010

  日期：2004.9

  We have designed arylfurylacryl-substituted benzophenones as non-thiol farnesyltransferase inhibitors utilizing a novel aryl binding site of farnesyltransferase. These compounds display activity in the low nanomolar range.

  我们已经设计了芳基呋喃基丙烯酸取代的二苯甲酮作为非硫醇法呢基转移酶抑制剂，利用了法呢基转移酶的新型芳基结合位点。这些化合物在低纳摩尔范围内显示活性。
• Structure-based discovery of new selective small-molecule sirtuin 5 inhibitors
  作者：Sha Liu、Sen Ji、Zhu-Jun Yu、Hua-Li Wang、Xu Cheng、Wei-Jian Li、Li Jing、Yamei Yu、Qiang Chen、Ling-Ling Yang、Guo-Bo Li、Yong Wu

  DOI：10.1111/cbdd.13077

  日期：2018.1

  Human sirtuin 5 (SIRT5) is a protein deacylase regulating metabolic pathways and stress responses and is implicated in metabolism-related diseases. Small-molecule inhibitors for SIRT5 are sought as chemical tools and potential therapeutics. Herein, we proposed a customized virtual screening approach targeting catalytically important and unique residues Tyr102 and Arg105 of SIRT5. Of the 20 tested virtual

  人Sirtuin 5（SIRT5）是一种蛋白质脱酰基酶，调节代谢途径和应激反应，并与代谢相关疾病有关。寻找用于SIRT5的小分子抑制剂作为化学工具和潜在的治疗剂。在这里，我们提出了针对SIRT5的催化重要且独特的Tyr102和Arg105残基的定制虚拟筛选方法。在测试的20个虚拟筛选结果中，有6种化合物显示出对SIRT5的明显抑制活性。对于命中化合物19，进行了一系列新合成的（E）-2-氰基-N-苯基-3-（5-苯基呋喃-2-基）丙烯酰胺衍生物/类似物的结构-活性关系分析，得出了新的更有效的抑制剂，其中37种对SIRT5表现出最强的抑制作用，IC 50值为5.59±0.75μM。生化研究表明，有37种可能是通过与琥珀酰赖氨酸底物而非NAD +辅因子竞争性抑制而起作用的，并且它显示出对SIRT5的选择性比SIRT2和SIRT6更高。这项研究将有助于进一步努力开发新的选择性SIRT5抑制剂作为工具和治疗剂。
• Preparation of Highly Functionalized Heterocyclic Zinc Organometallics via a Li(acac)-Catalysis of the I/Zn-Exchange Reaction
  作者：Paul Knochel、Liu-Zhu Gong

  DOI：10.1055/s-2004-837206

  日期：——

  of Li(acac) in NMP with various functionalized heterocyclic iodides provides new polyfunctional diheteroarylzincs, which undergo smooth Negishi cross-coupling reactions and CuCN.2LiCl-catalyzed allylation reactions under mild conditions. Remarkably, even an aldehyde function can be present in the diorganozinc reagents.

  在 NMP 中催化量的 Li(acac) 存在下，i-Pr 2 Zn 与各种功能化杂环碘化物的反应提供了新的多功能二杂芳基锌，其在温和条件下进行平滑的 Negishi 交叉偶联反应和 CuCN.2LiCl 催化的烯丙基化反应. 值得注意的是，甚至醛官能团也可以存在于二有机锌试剂中。