2-(四氢吡喃-2-基氧基)苯硼酸 | 502159-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(四氢吡喃-2-基氧基)苯硼酸
• 英文名称: 2-(tetrahydropyran-2-yloxy)-phenylboronic acid
• 英文别名: 2-(Tetrahydropyran-2-yloxy)phenylboronic acid；[2-(oxan-2-yloxy)phenyl]boronic acid
• CAS: 502159-01-5
• 化学式: C₁₁H₁₅BO₄
• 分子量: 222.049
• InChiKey: LLKRMUSMQFLZLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Tetrahydropyran-2-yloxy)phenylboronic 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: 2-(Tetrahydropyran-2-yloxy)phenylboronic acid
CAS number: 502159-01-5

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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: C11H15BO4
Molecular weight: 222.0

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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：

  2-(四氢吡喃-2-基氧基)苯硼酸 在 四(三苯基膦)钯 、 对甲苯磺酸 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 benzyl [2'-hydroxy-1,1'-biphenyl-3-yl]-acetate
  参考文献：
  名称：

  Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists

  摘要：

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.

  DOI：

  10.1021/jm060536g
• 作为产物：
  描述：

  2-苯氧基四氢吡喃 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2-(四氢吡喃-2-基氧基)苯硼酸
  参考文献：
  名称：

  过渡金属催化反应的合适配体的鉴定：苯乙烯对映选择性硼氢化中模块化配体库的筛选

  摘要：

  基于一般的模块化合成方案，可以从苯酚或萘酚衍生的骨架系统开始，以有效的分散方式获得各种手性双齿P / P-，P / S-，P / N-和P / Se配体。在氧化后处理后，在Rh催化的苯乙烯不对称硼氢化反应中测试了20个选定配体的文库，以产生高达91％ee的1-苯基乙醇。结果表明，配体结构的微小变化会导致原位生成的铑配合物的性能出现明显的，无法预测的差异。模块化方法应该适用于鉴定和优化其他过渡金属催化的转化的合适配体，而所需的努力相对较小。

  DOI：

  10.1002/1615-4169(200209)344:8<868::aid-adsc868>3.0.co;2-m

文献信息

• 一类芳氧基醚骨架的双金属配合物、制备方法及应用
  申请人：万华化学集团股份有限公司

  公开号：CN111943977B

  公开（公告）日：2023-03-24

  本发明提供了一类芳氧基醚骨架的双金属配合物、制备方法及应用。所述双金属配合物具有如下所示结构表达式。还有该双金属配合物的催化体系用于催化烯烃均聚或烯烃/α‑烯烃共聚合反应时表现出非常好的催化活性和热稳定性，并且催化生成的聚合产物具有较高的分子量和α‑烯烃插入率，具有很好的工业应用前景。
• Identification of Suitable Ligands for a Transition Metal-Catalyzed Reaction: Screening of a Modular Ligand Library in the Enantioselective Hydroboration of Styrene
  作者：Florian Blume、Saskia Zemolka、Thorsten Fey、Remo Kranich、Hans-Günther Schmalz

  DOI：10.1002/1615-4169(200209)344:8<868::aid-adsc868>3.0.co;2-m

  日期：2002.9

  general modular synthetic scheme, a variety of chiral bidentate P/P-, P/S-, P/N-, and P/Se-ligands is accessible in an efficient divergent manner starting from phenol or naphthol derived backbone systems. A library of 20 selected ligands was tested in the Rh-catalyzed asymmetric hydroboration of styrene to give 1-phenylethanol in up to 91% ee after oxidative work-up. It was demonstrated that small variations

  基于一般的模块化合成方案，可以从苯酚或萘酚衍生的骨架系统开始，以有效的分散方式获得各种手性双齿P / P-，P / S-，P / N-和P / Se配体。在氧化后处理后，在Rh催化的苯乙烯不对称硼氢化反应中测试了20个选定配体的文库，以产生高达91％ee的1-苯基乙醇。结果表明，配体结构的微小变化会导致原位生成的铑配合物的性能出现明显的，无法预测的差异。模块化方法应该适用于鉴定和优化其他过渡金属催化的转化的合适配体，而所需的努力相对较小。
• New Pyridine ONN-Pincer Gold and Palladium Complexes: Synthesis, Characterization and Catalysis in Hydrogenation, Hydrosilylation and CC Cross-Coupling Reactions
  作者：N. Debono、M. Iglesias、F. Sánchez

  DOI：10.1002/adsc.200700209

  日期：2007.11.5

  13C NMR spectroscopy. Palladium(II) and gold(III) complexes have been prepared as air-stable solids, with the ONN-tridentate ligand after deprotonation of the hydroxy group, the coordination of the metal ion is completely stereospecific and gives rise to only one diastereoisomer. These complexes were shown to be very active catalysts in the hydrogenation (80 % ee was achieved with the chiral gold complex)

  的ONN-三齿不对称钳形2- [6-（吡咯烷-1-基甲基）吡啶-2-基]苯酚和ñ -叔丁基-1 - [6-（2-羟基苯基）吡啶-2-基]甲基}吡咯烷-2-羧酰胺配体通过简便的方法合成，纯度高，收率高。所有的有机化合物都通过元素分析，质谱，IR和1 H和13 C NMR光谱进行了表征。钯（II）和金（III）配合物已制备为空气稳定的固体，羟基去质子化后具有ONN-三齿配体，金属离子的配位是完全立体定向的，仅产生一种非对映异构体。这些配合物在氢化反应中显示出非常活跃的催化作用（ee为80％ 在温和的条件下，通过手性金络合物，氢化硅烷化和CC偶联，Suzuki和Heck反应实现。
• Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists
  作者：Remo Kranich、Anke S. Busemann、Daniel Bock、Sabine Schroeter-Maas、Diana Beyer、Bo Heinemann、Michael Meyer、Katrin Schierhorn、Rainer Zahlten、Gerhard Wolff、Ewald M. Aydt

  DOI：10.1021/jm060536g

  日期：2007.3.1

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.