3-羟基-4-甲氧基苯硼酸 | 622864-48-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-羟基-4-甲氧基苯硼酸
• 英文名称: (3-hydroxy-4-methoxyphenyl)boronic acid
• CAS: 622864-48-6
• 化学式: C₇H₉BO₄
• mdl: MFCD12025997
• 分子量: 167.957
• InChiKey: YOPHDOOHKDJUAM-UHFFFAOYSA-N

物化性质

• 熔点：
  221 °C
• 沸点：
  380.5±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)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 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
• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Hydroxy-4-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: 3-Hydroxy-4-methoxyphenylboronic acid
CAS number: 622864-48-6

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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.
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：

  3-羟基-4-甲氧基苯硼酸 在 sodium borohydride acetate 、 potassium carbonate 、 溶剂黄146 、 C₉H₁₅O₂Rh 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 高倍甜味剂标准品
  参考文献：
  名称：

  一种爱德万甜的放大制备方法

  摘要：

  本发明公开了一种爱德万甜的放大制备方法，属于有机合成领域。采用两种方法：A、以丙烯醛和联硼酸频哪醇酯为原料，在铜盐和有机碱催化下水溶液中反应，得到3‑硼酸频哪醇酯丙醛；接着与5‑溴‑2‑甲氧基苯酚在钯催化剂和碱存在下，生成3‑羟基‑4‑甲氧基苯丙醛；B、将5‑溴‑2‑甲氧基苯酚格氏交换后，接着与硼酸酯反应，得到3‑羟基‑4‑甲氧基苯硼酸；接着与丙烯醛在铑催化剂和碱存在下，生成3‑羟基‑4‑甲氧基苯丙醛；最后还原胺环得到爱德万甜。该方法降低了异构体的生成量，提高了反应收率，工艺简单可靠、易于工业化生产，为爱德万甜的合成提供了新的反应路径。

  公开号：

  CN117820101A
• 作为产物：
  描述：

  2-(苄氧基)-4-溴苯甲醚 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-羟基-4-甲氧基苯硼酸
  参考文献：
  名称：

  Combretastatins 4-芳基香豆素类似物的合成和生物学评估。第2部分

  摘要：

  通过交叉偶联反应制备与康普他汀A-4相关的一系列A环的各种甲氧基化的4-（3-羟基-4-甲氧基苯基）香豆素。细胞毒性研究表明，它对HBL100细胞系具有有效的活性。A环上的取代模式仅对抗增殖活性有轻微影响。对于大多数细胞毒性化合物，评估了其作为P-gp和BCRP外排泵潜在调节剂的活性。结果表明，化合物2和7能够以与环孢霉素A相似的浓度恢复米托蒽醌累积（BCRP）。化合物7是逆转P-gp活性的最有效方法。发现所有化合物大部分通过亚化学计量作用模式有效抑制体外微管形成。发现化合物1和2的表观亲和力结合常数与康布雷他汀A-4相似，即1×10 6 M –1。香豆素衍生物的分子模型是根据7的分子结构进行的，这是通过单晶X射线晶体学确定的。该计算表明，在色酮部分平面之外的甲氧基的存在是重要的空间位阻因子，其将这些分子的可及性嵌入微管蛋白上的结合口袋内。

  DOI：

  10.1021/jm901826e

文献信息

• Design, Synthesis, and Biological Evaluation of Novel Pyridine-Bridged Analogues of Combretastatin-A4 as Anticancer Agents
  作者：Shilong Zheng、Qiu Zhong、Madhusoodanan Mottamal、Qiang Zhang、Changde Zhang、Elise LeMelle、Harris McFerrin、Guangdi Wang

  DOI：10.1021/jm500002k

  日期：2014.4.24

  A series of novel pyridine-bridged analogues of combretastatin-A4 (CA-4) were designed and synthesized. As expected, the 4-atom linker configuration retained little cytotoxicities in the compounds 2e, 3e, 3g, and 4i. Activities of the analogues with 3-atom linker varied widely depending on the phenyl ring substitutions, and the 3-atom linker containing nitrogen represents the more favorable linker

  设计并合成了一系列新型吡啶桥连的考布他汀-A4 (CA-4) 类似物。正如预期的那样，4 原子接头构型在化合物2e、3e、3g和4i 中几乎没有细胞毒性。具有 3 原子接头的类似物的活性因苯环取代而有很大差异，含氮的 3 原子接头代表更有利的接头结构。其中，三种类似物（4h、4s和4t）以与 CA-4 相当的方式在体内有效抑制细胞存活和生长、阻止细胞周期并阻断血管生成和脉管系统形成。叠加4H和微管蛋白的秋水仙碱结合口袋中的4s显示 CA- 4、4h和4s的结合姿势是相似的，正如竞争性结合试验所证实的，其中测量了配体替代微管蛋白结合的秋水仙碱的能力。结合数据与观察到的抗增殖和抑制血管生成的生物活性一致，但不能预测它们的抗微管蛋白聚合活性。
• [EN] MACROCYCLIC FLT3 KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE FLT3 MACROCYCLIQUES
  申请人：ONCODESIGN SA

  公开号：WO2013045653A1

  公开（公告）日：2013-04-04

  The present invention relates to macrocylic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of FLT3 (FMS-Related Tyrosine kinase 3). Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the treatment of cell proliferative disorders, such as cancer.

  本发明涉及大环化合物以及含有作为激酶抑制剂，特别是FLT3（FMS相关酪氨酸激酶3）抑制剂的所述化合物的组合物。此外，本发明还提供了所述化合物的制备过程，以及使用它们的方法，例如作为药物，特别用于治疗细胞增殖紊乱，如癌症。
• MACROCYCLIC FLT3 KINASE INHIBITORS
  申请人：ONCODESIGN S.A.

  公开号：US20140303159A1

  公开（公告）日：2014-10-09

  The present invention relates to macrocylic compounds and compositions containing said compounds acting as kinase inhibitors, in particular as inhibitors of FLT3 (FMS-Related Tyrosine kinase 3). Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the treatment of cell proliferative disorders, such as cancer.

  本发明涉及大环化合物以及含有作为激酶抑制剂，特别是FLT3（FMS相关酪氨酸激酶3）抑制剂的所述化合物的组合物。此外，本发明还提供了所述化合物的制备过程，以及使用它们的方法，例如作为药物，特别用于治疗细胞增殖紊乱，如癌症。
• Design, synthesis and bioevaluation of 6-aryl-1-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazoles as tubulin polymerization inhibitors
  作者：Runlai Liu、Mingxin Huang、Shuai Zhang、Long Li、Mi Li、Jun Sun、Lan Wu、Qi Guan、Weige Zhang

  DOI：10.1016/j.ejmech.2021.113826

  日期：2021.12

  6-aryl-1-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazoles as tubulin polymerization inhibitors targeting the colchicine-binding site were designed to restrict bioactive configuration of (Z,E)-vinylogous CA-4. All of the target compounds were synthesized and then evaluated for their in vitro antiproliferative activities. Among them, 2a exhibited the most potent activities against three cancer cell lines with IC50

  一系列新的 6-aryl-1-(3,4,5-trimethoxyphenyl)-1 H - benzo[ d ]imidazoles 作为微管蛋白聚合抑制剂靶向秋水仙碱结合位点，旨在限制 ( Z,E )的生物活性构型-插藤CA-4。合成所有目标化合物，然后评估其体外抗增殖活性。其中，2a对三种癌细胞系表现出最有效的活性，IC 50值在0.037-0.20 μM范围内。进一步的机制研究表明，2a抑制微管蛋白聚合，破坏细胞微管网络，在 G2/M 期阻止细胞周期，诱导细胞凋亡并阻碍癌细胞迁移。此外，2a在 4T1 异种移植小鼠模型中显示出显着的体内抗肿瘤功效，在 2.5 mg/kg 的剂量下肿瘤生长抑制率为 52%。秋水仙碱竞争试验和2a与微管蛋白复合物的对接模型表明2a作用于秋水仙碱结合位点。
• Synthesis and Structure-Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4
  作者：Martin Arthuis、Renée Pontikis、Guy G. Chabot、Johanne Seguin、Lionel Quentin、Stéphane Bourg、Luc Morin-Allory、Jean-Claude Florent

  DOI：10.1002/cmdc.201100154

  日期：2011.9.5

  A series of combretastatin A4 (CA4) analogues with a lactam or lactone ring fused to the trimethoxyphenyl or the B‐phenyl moiety were synthesized in an efficient and stereoselective manner by using a domino Heck–Suzuki–Miyaura coupling reaction. The vascular‐disrupting potential of these conformationally restricted CA4 analogues was assessed by various in vitro assays: inhibition of tubulin polymerization

  通过使用多米诺Heck-Suzuki-Miyaura偶联反应以高效且立体选择性的方式合成了一系列具有内酰胺或内酯环与三甲氧基苯基或B-苯基部分融合的康维他汀A4（CA4）类似物。这些构象受限的CA4类似物的破坏血管的潜力通过各种体外测定法进行了评估：微管蛋白聚合的抑制，内皮细胞形态的改变以及内皮细胞线的破坏。还评估了化合物对鼠和人肿瘤细胞的生长抑制作用。含有羟吲哚环（与带有苯并呋喃酮环的化合物相比）受B环约束的衍生物以及带有与三甲氧基苯基环稠合的六元内酯核的类似物具有显着的生物活性。9 b）特别令人感兴趣，因为它结合了化学稳定性和血管分裂剂的生物学活性特征。