3-甲氧基-4-羧基苯硼酸 | 851335-12-1

• 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: 3-甲氧基-4-羧基苯硼酸
• 英文名称: 4-borono-2-methoxybenzoic acid
• 英文别名: 3-Methoxy-4-carboxyphenylboronic acid
• CAS: 851335-12-1
• 化学式: C₈H₉BO₅
• mdl: MFCD06656278
• 分子量: 195.967
• InChiKey: ASOXJGFTNRPKEN-UHFFFAOYSA-N

物化性质

• 沸点：
  430.7±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,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: 3-Methoxy-4-carboxyphenylboronic 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: 3-Methoxy-4-carboxyphenylboronic acid
CAS number: 851335-12-1

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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: C8H9BO5
Molecular weight: 196.0

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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：

  3-甲氧基-4-羧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 2-Methoxy-N-(4-trifluoromethyl-phenyl)-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide
  参考文献：
  名称：

  从芳基脲到联芳基酰胺再到氨基喹唑啉：发现新型有效的TRPV1拮抗剂。

  摘要：

  铅VR1拮抗剂1中芳基环的哌嗪生物等位取代导致了联芳基酰胺系列的产生。B环SAR的发展导致构象受限的类似物70。所得氨基喹唑啉70代表一种新型VR1拮抗剂，与先导系列的类似化合物相比，具有更高的体外效价和口服生物利用度。

  DOI：

  10.1016/j.bmcl.2006.07.010
• 作为产物：
  描述：

  四羟基二硼 、 4-碘-2-甲氧基苯甲酸 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 四甲基醋酸铵 作用下， 以 2-甲基四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 3-甲氧基-4-羧基苯硼酸
  参考文献：
  名称：

  钯和镍基体系用于芳基（假）卤化物与B2（OH）4的催化硼化反应。

  摘要：

  尽管在金属催化的芳基（假）卤化物的硼化反应方面取得了最新进展，但仍需要开发出可靠的方法来获得可用于进一步官能化的早期和晚期有机硼中间体。尤其是，在广泛的亲电子伙伴中，在温和的反应条件下运行的通用催化系统的开发仍然难以实现。本文中，我们报道了使用四羟基二硼（B 2（OH）4）进行芳基（假）卤化物直接硼化的三种催化体系（两种基于Pd的体系和一种基于Ni的体系）的开发和应用）。对于基于Pd的催化剂体系，我们已经确定了一般的反应条件，该条件允许通过简单的沉淀来螯合卤离子，从而导致催化剂负载量低至0.01 mol％（100 ppm），反应温度低至室温。我们还描述了一种互补的基于Ni的催化剂体系，该体系采用简单的未连接的Ni（II）盐作为对基于Pd的芳基（假）卤化物进行硼化的体系的廉价替代品。在先进的中间体和原料药上，还证明了将所有三个系统外推至一锅串联硼化/ Suzuki-Miyaura交叉偶联。

  DOI：

  10.1021/acs.joc.0c00929

文献信息

• Structure-activity relationship study of the pyridine moiety of isothiazolo[4,3-b]pyridines as antiviral agents targeting cyclin G-associated kinase
  作者：Belén Martinez-Gualda、Szu-Yuan Pu、Mathy Froeyen、Piet Herdewijn、Shirit Einav、Steven De Jonghe

  DOI：10.1016/j.bmc.2019.115188

  日期：2020.1

  promising antiviral activity. In this manuscript, the structure-activity relationship study was expanded to synthesis of isothiazolo[4,3-b]pyridines with modifications of the pyridine moiety. This effort led to the discovery of an isothiazolo[4,3-b]pyridine derivative with a 3,4-dimethoxyphenyl residue at position 5 that displayed low nanomolar GAK binding affinity and antiviral activity against dengue

  以前，我们报道了3,6-二取代异噻唑并[4,3-b]吡啶的发现，它是有效的和选择性的细胞周期蛋白G相关激酶（GAK）抑制剂，具有有希望的抗病毒活性。在该手稿中，结构-活性关系研究扩展到合成具有吡啶部分修饰的异噻唑并[4,3-b]吡啶。这项工作导致发现了在位置5具有3,4-二甲氧基苯基残基的异噻唑并[4,3-b]吡啶衍生物，该衍生物显示出低的纳摩尔GAK结合亲和力和抗登革热病毒的抗病毒活性。
• [EN] SUBSTITUTED TRIAZOLOPYRIDINES<br/>[FR] TRIAZOLOPYRIDINES SUBSTITUÉES
  申请人：BAYER PHARMA AG

  公开号：WO2011157688A1

  公开（公告）日：2011-12-22

  The present invention relates to substituted triazolopyridine compounds of general formula (I) : in which R1, R2, R3, R4, and R5 are as given in the description and in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease of uncontrolled cell growth, proliferation and/or survival as well as to the use of intermediate compounds for the preparation of said compounds.

  本发明涉及通式（I）的取代三唑吡啶化合物，其中R1、R2、R3、R4和R5如描述和索赔中所述，以及制备所述化合物的方法，包括所述化合物的药物组合物和组合物，用于制造用于治疗或预防细��生长、增殖和/或存活失控疾病的药物组合物以及用于制备所述化合物的中间化合物的用途。
• C-3 benzoic acid derivatives of C-3 deoxybetulinic acid and deoxybetulin as HIV-1 maturation inhibitors
  作者：Zheng Liu、Jacob J. Swidorski、Beata Nowicka-Sans、Brian Terry、Tricia Protack、Zeyu Lin、Himadri Samanta、Sharon Zhang、Zhufang Li、Dawn D. Parker、Sandhya Rahematpura、Susan Jenkins、Brett R. Beno、Mark Krystal、Nicholas A. Meanwell、Ira B. Dicker、Alicia Regueiro-Ren

  DOI：10.1016/j.bmc.2016.03.001

  日期：2016.4

  A series of C-3 phenyl- and heterocycle-substituted derivatives of C-3 deoxybetulinic acid and C-3 deoxybetulin was designed and synthesized as HIV-1 maturation inhibitors (MIs) and evaluated for their antiviral activity and cytotoxicity in cell culture. A 4-subsituted benzoic acid moiety was identified as an advantageous replacement for the 3′3′-dimethylsuccinate moiety present in previously disclosed

  设计并合成了一系列C-3脱氧贝丁酸和C-3脱氧贝丁酸的C-3苯基和杂环取代衍生物，作为HIV-1成熟抑制剂（MIs），并评估了它们在细胞培养中的抗病毒活性和细胞毒性。鉴定出4-取代的苯甲酸部分是先前公开的MI中存在的3'3'-二甲基琥珀酸酯部分的有利替代物，其阐明了药效团的拓扑学的新方面。与原型HIV-1 MI bevirimat（1，BVM）相比，新的类似物对野生型（wt）病毒具有出色的体外抗病毒活性，并且血清转移降低，这是临床研究中第一个评估的MI。化合物9a对wt病毒表现出与1类似的细胞培养能力（ 对于9a， WT EC 50 = 16 nM，而对于1a，则为10 nM ）。但是，9a的效力受人血清的影响较小，而该化合物在大鼠中的药代动力学特征与1相似。因此，9a（脱氧贝丁酸的4-苯甲酸衍生物）代表了探索第二代MI设计的新起点。
• General Access to <i>C</i>-Centered Radicals: Combining a Bioinspired Photocatalyst with Boronic Acids in Aqueous Media
  作者：Maheshwerreddy Chilamari、Jacob R. Immel、Steven Bloom

  DOI：10.1021/acscatal.0c03422

  日期：2020.11.6

  indispensable building blocks for modern synthetic chemistry. In recent years, visible light photoredox catalysis has become a promising avenue to access C-centered radicals from a broad array of latent functional groups, including boronic acids. Herein, we present an aqueous protocol wherein water features a starring role to help transform aliphatic, aromatic, and heteroaromatic boronic acids to C-centered

  以碳为中心的自由基是现代合成化学必不可少的组成部分。近年来，可见光光氧化还原催化已成为从包括硼酸在内的广泛的潜在官能团中进入以C为中心的自由基的有前途的途径。在本文中，我们介绍了一种水性方案，其中水起着星形作用，以帮助将脂族，芳族和杂芳族硼酸转化为C具有生物启发性的黄素光催化剂的中心自由基。这些自由基通过开壳共轭物加成到不同的Michael受体上，以递送各种不同的烷基化产物，包括三种药学上相关的化合物。通过计算研究，氘标记，自由基捕获实验和光谱分析研究了反应机理。
• [EN] AMINOQUINOLINE DERIVATIVES AS ANTIVIRAL AGENTS<br/>[FR] DÉRIVÉS D'AMINOQUINOLÉINE COMME AGENTS ANTIVIRAUX
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012037108A1

  公开（公告）日：2012-03-22

  Provided are compounds of Formula (I) and Formula (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

  提供的是式(I)和式(II)的化合物及其药用盐，它们的药物组合物，它们的制备方法，以及它们用于治疗由黄病毒科病毒介导的病毒感染，如丙型肝炎病毒（HCV）。