3-(苄氧基)-4-甲氧基苯硼酸 | 243990-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(苄氧基)-4-甲氧基苯硼酸
• 英文名称: (3-(benzyloxy)-4-methoxyphenyl)boronic acid
• 英文别名: 3-(Benzyloxy)-4-methoxyphenylboronic acid；(4-methoxy-3-phenylmethoxyphenyl)boronic acid
• CAS: 243990-54-7
• 化学式: C₁₄H₁₅BO₄
• 分子量: 258.082
• InChiKey: GKHSIZCQILKQCU-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(Benzyloxy)-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-(Benzyloxy)-4-methoxyphenylboronic acid
CAS number: 243990-54-7

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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: C14H15BO4
Molecular weight: 258.1

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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-(苄氧基)-4-甲氧基苯硼酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 24.0h， 生成 4-(3'-hydroxy-4'-methoxyphenyl)-5-methoxycoumarin
  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
• 作为产物：
  描述：

  2-(苄氧基)-4-溴苯甲醚 在 正丁基锂 、 硼酸三异丙酯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(苄氧基)-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

• [EN] THIENO[3,2-C]PYRIDIN-4(5H)-ONES AS BET INHIBITORS<br/>[FR] THIÉNO[3,2-C]PYRIDIN-4(5H)-ONES UTILES COMME INHIBITEURS DE BET
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2014078257A1

  公开（公告）日：2014-05-22

  Thienopyridone compounds of formula (I) or a salt thereof, pharmaceutical compositions containing such compounds and their use in therapy, in particular in the treatment of diseases or conditions for which a bromodomain inhibitor is indicated.

  噻诺吡啶酮化合物或其盐，含有该化合物的药物组合物及其在治疗中的用途，特别是在溴结构域抑制剂用于治疗的疾病或症状中。
• Cyclic bridged analogs of isoCA-4: Design, synthesis and biological evaluation
  作者：Shannon Pecnard、Olivier Provot、Hélène Levaique、Jérome Bignon、Laurie Askenatzis、Francois Saller、Delphine Borgel、Sophie Michallet、Marie-Catherine Laisne、Laurence Lafanechère、Mouad Alami、Abdallah Hamze

  DOI：10.1016/j.ejmech.2020.112873

  日期：2021.1

  In this work, a series of cyclic bridged analogs of isocombretastatin A-4 (isoCA-4) with phenyl or pyridine linkers were designed and synthesized. The synthesis of the desired analogs was performed by the formation of nitro-vinyl intermediates, followed by a Cadogan cyclization. Structure activity relationship (SAR) study demonstrates the critical role of the combination of quinaldine as ring A, pyridine

  在这项工作中，设计并合成了一系列具有苯或吡啶连接基的异康他汀A-4（iso CA-4）的环状桥连类似物。所需类似物的合成通过形成硝基-乙烯基中间体，然后进行Cadogan环化来进行。结构活性关系（SAR）研究表明，在同一分子中，奎尼丁（作为环A），吡啶（作为连接基）和吲哚（作为B环）的组合对于细胞毒活性具有关键作用。在所有测试的化合物中，化合物42对一组癌细胞具有最高的抗增殖活性，平均IC50值为5.6 nM。另外，化合物42对过表达MDR1的K562R细胞系显示出高的抗增殖活性；因此，它的活性分别比参考化合物iso CA-4和CA-4高1.5倍和12倍。此外，有42种化合物对结肠癌细胞（HT-29）表现出强大的抗增殖活性，该细胞对康布雷他汀A-4和iso CA-4有抵抗力，并且发现其活性是天然CA-4的8000倍。 。化合物42还有效地抑制了体外和细胞中的微管蛋白聚合，并诱导了G2 /
• Synthesis and anti-inflammatory activity of isoquebecol
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  DOI：10.1016/j.bmc.2017.01.050

  日期：2017.4

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• 二芳基取代稠杂环类化合物及其制备方法和在制药中的用途
  申请人：复旦大学

  公开号：CN111732584A

  公开（公告）日：2020-10-02

  本发明属合成药物化学领域，涉及二芳基取代稠杂环类化合物，具体涉及二芳基取代咪唑并[4,5‑c]吡啶和咪唑并[4,5‑c]吡啶‑2‑酮类化合物或其药学盐化合物及其在制药中的应用。本发明还包括所述化合物、其药用盐及其药物组合物在制备预防或治疗与肿瘤相关疾病药物中的应用。本发明提供的化合物或其在药学上可接受的盐具有优秀的Tubulin/Katanin双重作用、多种肿瘤细胞增殖抑制活性以及体内抗肿瘤活性，可应用于制备预防或治疗与肿瘤相关疾病的药物；所述与肿瘤相关疾病包括良、恶性肿瘤以及肿瘤引起的其他疾病。
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  作者：Yanzhao Wang、Jingzhao Xia、Guoqiang Yang、Wanbin Zhang

  DOI：10.1016/j.tet.2017.12.015

  日期：2018.1

  An Ir-catalyzed asymmetric hydrogenation of 2-substituted 1,4-benzodioxines was developed for the preparation of chiral 1,4-benzodioxanes, which are present in numerous biologically active compounds and natural products. Our tropos biphenyl phosphine-oxazoline ligand is essential for obtaining good ee. A broad range of substrates were tolerable to the reaction conditions and gave the corresponding

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