(4-羟基-3-甲氧基苯基)硼酸 | 182344-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (4-羟基-3-甲氧基苯基)硼酸
• 中文别名: D-天冬氨酸,3-氟-,苏-(9CI)
• 英文名称: (4-hydroxy-3-methoxyphenyl)boronic acid
• 英文别名: 4-hydroxy-3-(methoxy)phenylboronic acid；4-hydroxy-3-methoxyphenylboronic acid；3-methoxy-4-hydroxyphenyl boronic acid
• CAS: 182344-21-4
• 化学式: C₇H₉BO₄
• 分子量: 167.957
• InChiKey: UZFBWSFTHSYXCN-UHFFFAOYSA-N

物化性质

• 沸点：
  377.6±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 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: 4-Hydroxy-3-methoxyphenylboronic 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: 4-Hydroxy-3-methoxyphenylboronic acid
CAS number: 182344-21-4

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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, under −20◦C.
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: C7H9BO4
Molecular weight: 168.0

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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：

  (4-羟基-3-甲氧基苯基)硼酸 在 palladium diacetate 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 potassium fluoride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.33h， 生成 Trifluoro-methanesulfonic acid 3-methoxy-4'-methyl-biphenyl-4-yl ester
  参考文献：
  名称：

  Repetitive Two-step Method for Oligoarene Synthesis through Rapid Cross-coupling of Hydroxyphenylboronic Acids and Anhydrides

  摘要：

  在钯催化的交叉偶联步骤中使用了羟基苯硼酸或酸酐，开发出了一种用于合成低聚烯烃的两步式 Suzuki-Miyaura 偶联-三氟化反应程序。

  DOI：

  10.1246/cl.2006.164
• 作为产物：
  描述：

  4-溴邻甲氧基苯酚 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium periodate 、 potassium acetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 (4-羟基-3-甲氧基苯基)硼酸
  参考文献：
  名称：

  (−)-Amovillosumin A 的全合成和 (−)-Amovillosumin C 的化学合成结构校正

  摘要：

  去甲木脂素是从多种植物中分离出来的一类罕见的天然产物，其中许多具有有趣的生物活性，包括抗菌、抗氧化、植物毒性、血小板聚集抑制作用等。 amovillosumins A ( 1 ) 和 C ( 3 ) 是从砂仁(Amomi Fructus) 中分离出来的去甲木脂素，由于其具有有趣的生物活性，特别是能够增加胰高血糖素样肽-1 (GLP-) 的刺激，因此对其合成感兴趣。 1）分泌。本研究利用关键中间体15立体选择性合成( 7R , 8R )-amovillosumins A( 1 )和C( 3 )。所开发的方法包括 Mitsunobu 偶联、改进的铑催化 Miyaura 芳基化以及关键成键步骤中的酸催化环化。合成后， 1的结构得到确认，但发现文献中提出的amovillosumin C( 3 )的含苯并二恶烷的结构是错误的。因此，通过进一步研究，通过合成实现了3的结构修正，正确的结构是8- O -4'-羟基去木脂素。

  DOI：

  10.1021/acs.jnatprod.3c01069

文献信息

• Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators
  作者：Iain R. Greig、Gemma L. Baillie、Mostafa Abdelrahman、Laurent Trembleau、Ruth A. Ross

  DOI：10.1016/j.bmcl.2016.08.018

  日期：2016.9

  CB1-mediated effects. Thus, a greater range of molecular tools are required to allow definitive elucidation of the effects of CB1 allosteric modulation. In this study, we show a novel series of indole sulfonamides. Compounds 5e and 6c (ABD1075) had potencies of 4 and 3nM respectively, and showed good oral exposure and CNS penetration, making them highly versatile tools for investigating the therapeutic

  现有的CB1阴性变构调节剂（NAM）属于结构类别的有限范围。尽管具有CB1 NAM的理论潜力，但已发表的体内研究通常不能证明预期的与治疗相关的CB1介导的作用。因此，需要更大范围的分子工具才能明确阐明CB1变构调节作用。在这项研究中，我们显示了一系列新颖的吲哚磺酰胺。化合物5e和6c（ABD1075）的效力分别为4和3nM，并显示出良好的口服暴露和CNS渗透性，使其成为研究大麻素系统的变构调节作用的潜在治疗工具。
• Indolin-2-one derivatives as selective Aurora B kinase inhibitors targeting breast cancer
  作者：Eman M.E. Dokla、Amal Kamal Abdel-Aziz、Sandra N. Milik、Amr H. Mahmoud、Mona Kamal Saadeldin、Martin J. McPhillie、Saverio Minucci、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2021.105451

  日期：2021.12

  indicated that 6e and 8a induced G2/M cell cycle arrest, apoptosis, and necrosis of MDA-MB-468 cells and western blot analysis of 8a effect on MDA-MB-468 cells revealed 8a‘s ability to reduce Aurora B and its downstream target, Histone H3 phosphorylation. 6e and 8a displayed better safety profiles than multikinase inhibitors such as sunitinib, showing no cytotoxic effects on normal rat cardiomyoblasts

  Aurora B 是一种关键的细胞周期调节剂，其功能错误会导致多倍体、遗传不稳定和肿瘤发生。它在许多癌症中过度表达，因此，用小分子抑制剂靶向 Aurora B 构成了一种有前途的抗癌治疗方法。在基于结构的设计和分子杂交方法的指导下，我们基于先前报道的基于 indolin-2-one 的多激酶抑制剂开发了一系列十五种 indolin-2-one 衍生物 ( 1 )。七种衍生物5g、6a、6c - e、7和8a在 NCI-60 细胞系筛选中显示出优先的抗增殖活性，其中氨基甲酸酯6e和环丙基脲8a衍生物对 Aurora B（IC 50 分别为 16.2 和 10.5 nM）和 MDA-MB-468 细胞（IC 50  = 32.6 ± 9.9 和 29.1 ± 7.3 nM）显示出最佳活性。此外，6e和8a损害了 MDA-MB-468 细胞的克隆形成潜力。机制研究表明，6e和8a诱导 MDA-MB-468
• [EN] ISOTHIAZOLOQUINOLONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS<br/>[FR] ANTI-INFECTIEUX A BASE D'ISOTHIAZOLOQUINOLONES ET DE SELS CORRESPONDANTS
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2005019228A1

  公开（公告）日：2005-03-03

  The invention provides compounds and salts of Formula (I) and Formula (II): which possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula (I) and Formula (II). The variables A1, R2, R3, R5, R6, R7, A8 and R9 are defined herein. Certain compounds of Formula (I) and Formula (II) disclosed herein are potent and selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula (I) or Formula (II) and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula (I) or Formula (II) as the only active agent or may contain a combination of a compound of Formula (I) or Formula (II) and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

  本发明提供了具有抗菌活性的公式(I)和公式(II)的化合物及盐类：本发明还提供了用于制造公式(I)和公式(II)化合物的新的合成中间体。变量A1、R2、R3、R5、R6、R7、A8和R9在此文中定义。本文披露的某些公式(I)和公式(II)化合物是细菌DNA合成和细菌复制的强效和选择性抑制剂。本发明还提供了含有一种或多种公式(I)或公式(II)化合物以及一种或多种载体、辅料或稀释剂的抗菌组合物，包括药物组合物。这样的组合物可以只含有公式(I)或公式(II)的化合物作为唯一的活性成分，也可以含有公式(I)或公式(II)的化合物与一种或多种其他活性成分的组合。本发明还提供了用于治疗动物微生物感染的方法。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS D'UTILISATION
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2015058084A1

  公开（公告）日：2015-04-23

  The present application discloses compounds that are inhibitors of Btk, compounds that are inhibitors of ΡΒΚδ, and compounds that are dual inhibitors of both Btk and PI3Kδ. Also described are methods for synthesizing such inhibitors and methods for using such inhibitors for the treatment of diseases wherein inhibition of Btk and PI3Kδ provides a therapeutic benefit to a patient having the disease.

  本申请公开了抑制Btk的化合物、抑制ΡΒΚδ的化合物，以及既是Btk又是PI3Kδ的双重抑制剂的化合物。还描述了合成这些抑制剂的方法，以及利用这些抑制剂治疗疾病的方法，其中抑制Btk和PI3Kδ对患有该疾病的患者提供治疗益处。
• [EN] NOVEL COMPOUNDS AND THEIR USE IN THERAPY<br/>[FR] COMPOSÉS INÉDITS ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：BIOCHROMIX PHARMA AB

  公开号：WO2013009259A1

  公开（公告）日：2013-01-17

  The present invention relates to novel chemical compounds formula (I) (C)n-B-(A)m-B-(C)n (I) wherein m is 0 or 1, and n is independently 0, 1, 2 or 3, A, each B and each C are independently selected from phenylene and five-and six-membered heteroaromatic rings, and for a terminal ring B or C also from bicyclic heteroaromatic fused rings having seven to ten ring members, wherein the bond between at least two of the rings A to C may be replaced by a carbonyl group (-CO-), wherein at least two of the rings A to C are substituted with one or two groups R, and wherein each ring A to C further optionally is substituted with one or two groups R1. The compounds are useful in therapy, especially therapy of a mammal suffering from a disease involving misfolded or aggregated forms of proteins.

  本发明涉及一种新型化合物的化学式（I）（C）n-B-（A）m-B-（C）n（I），其中m为0或1，n独立地为0、1、2或3，A、每个B和每个C独立地选自苯基和五元和六元杂芳环，对于末端环B或C还可以选自具有七至十个环成员的双环杂芳融合环，其中至少两个环A到C之间的键可以被羰基（-CO-）取代，其中至少两个环A到C被一个或两个基团R取代，每个环A到C还可以选择地被一个或两个基团R1取代。这些化合物在治疗中有用，特别是在治疗患有涉及蛋白质错误折叠或聚集形式的疾病的哺乳动物的治疗中。