2-((3-(三氟甲基)苯氧基)甲基)苯硼酸 | 1072951-60-0

• 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: 2-((3-(三氟甲基)苯氧基)甲基)苯硼酸
• 中文别名: 2-[(3'-(三氟甲基)苯氧基)甲基]苯硼酸；2-[(3'-(三氟甲基)苯氧基)甲基]苯基硼酸
• 英文名称: 2-[(3-(trifluoromethyl)phenoxy)methyl]phenylboronic acid
• 英文别名: (2-((3-(Trifluoromethyl)phenoxy)methyl)phenyl)boronic acid；[2-[[3-(trifluoromethyl)phenoxy]methyl]phenyl]boronic acid
• CAS: 1072951-60-0
• 化学式: C₁₄H₁₂BF₃O₃
• 分子量: 296.054
• InChiKey: YCLVPNCQCUGEIR-UHFFFAOYSA-N

物化性质

• 熔点：
  97-101 °C
• 沸点：
  427.5±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险类别码：
  R22
• 海关编码：
  2931900090
• 危险标志：
  GHS07
• 危险性描述：
  H302,H413

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-((3-(Trifluoromethyl)phenoxy)methyl)phenylboronic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H413: May cause long lasting harmful effects to aquatic life

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Section 3. Composition/information on ingredients.
Ingredient name: 2-((3-(Trifluoromethyl)phenoxy)methyl)phenylboronic acid
CAS number: 1072951-60-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H12BF3O3
Molecular weight: 296.0

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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, hydrogen fluoride.

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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-((3-(三氟甲基)苯氧基)甲基)苯硼酸 、 5-碘水杨酸甲酯 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以73%的产率得到2-hydroxy-5-[2-(3-trifluoromethylphenoxymethyl)phenyl]-benzoic acid potassium salt
  参考文献：
  名称：

  水杨酸衍生物抑制原发性高草酸尿症1型小鼠肝细胞中草酸盐的产生。

  摘要：

  原发性高草酸尿症1型（PH1）是一种与乙醛酸代谢有关的罕见的威胁生命的遗传疾病，其特征是草酸钙晶体的积累。当前的治疗涉及肝和/或肾移植，这些过程具有显着的发病率和死亡率，并且需要长期的免疫抑制。因此，迫切需要药物治疗。我们在这里介绍水杨酸衍生物的空前活性，它是能够在低微摩尔范围内降低高草酰脲肝细胞中草酸盐输出的试剂，这意味着其在治疗PH1中的潜在用途。尽管这种表型活性与乙醇酸氧化酶（GO）抑制的相关性尚待验证，但此处描述的大多数水杨酸都是具有IC 50的GO抑制剂值低至3μM。水杨酸在GO内部的结合模式已通过计算机方法进行了研究，并建立了初步的结构-活性关系。类化合物的药物结构和易合成性使其成为结构优化的有前途的命中方法。

  DOI：

  10.1021/acs.jmedchem.8b00399

文献信息

• Virtual Fragment Screening Identification of a Quinoline-5,8-dicarboxylic Acid Derivative as a Selective JMJD3 Inhibitor
  作者：Assunta Giordano、Federica del Gaudio、Catrine Johansson、Raffaele Riccio、Udo Oppermann、Simone Di Micco

  DOI：10.1002/cmdc.201800198

  日期：2018.6.20

  The quinoline‐5,8 dicarboxylic acid scaffold has been identified by a fragment‐based approach as new potential lead compound for the development of JMJD3 inhibitors. Among them, 3‐(2,4‐dimethoxypyrimidin‐5‐yl)quinoline‐5,8‐dicarboxylic acid (compound 3) shows low micromolar inhibitory activity against Jumonji domain‐containing protein 3 (JMJD3). The experimental evaluation of inhibitory activity against

  喹啉5,8二羧酸支架已被基于片段的方法鉴定为开发JMJD3抑制剂的新的潜在先导化合物。其中，3-（2,4-二甲氧基嘧啶-5-基）喹啉-5,8-二羧酸（化合物3）对含有Jumonji域的蛋白3（JMJD3）的微摩尔抑制活性较低。对JMJD3的七个相关同工型的抑制活性的实验评估突显了对目标生物学靶标的前所未有的选择性。
• Discovery of new potent molecular entities able to inhibit mPGES-1
  作者：Simone Di Micco、Stefania Terracciano、Vincenza Cantone、Katrin Fischer、Andreas Koeberle、Antonio Foglia、Raffaele Riccio、Oliver Werz、Ines Bruno、Giuseppe Bifulco

  DOI：10.1016/j.ejmech.2017.10.039

  日期：2018.1

  disclosed molecules, except for LY3023705, which recently entered clinical trials, are available for clinical use, therefore the discovery of new effective mPGES-1 inhibitors with increased drug–like properties are urgently needed. Continuing our work aimed at identifying new chemical platforms able to interact with this enzyme, here we describe the discovery of potent mPGES-1 modulators, featuring a 1-fluoro-2

  谷胱甘肽依赖性膜蛋白mPGES-1参与PGE 2的生产，已被公认为开发抗炎和抗癌药物的战略目标。已证明选择性控制炎症刺激诱导的PGE 2水平，既不影响组成性产生的PGE 2，也不影响稳态前列腺素，因此其调节可代表控制PGE 2的更好策略。与使用传统抗炎药相比，这种药物具有严重的副作用。尽管进行了深入的研究以鉴定有效的mPGES-1抑制剂作为药物开发的有吸引力的候选药物，但除LY3023705（最近进入临床试验）外，所公开的分子均无法用于临床，因此发现了新的有效mPGES-迫切需要1种具有类似药物特性的抑制剂。继续我们旨在鉴定能够与该酶相互作用的新化学平台的工作，在此我们描述了通过加工和对接一种有效的mPGES-1调节剂的发现，该调节剂具有基于1-氟-2,4-二硝基联苯的支架。少量可合成的分子集合，围绕两个主要片段构建，在我们的计算机筛选中披露。已合成并测试了得分最高的命中数据，其中五个预测
• Fragment-based discovery of potent inhibitors of the anti-apoptotic MCL-1 protein
  作者：Andrew M. Petros、Steven L. Swann、Danying Song、Kerren Swinger、Chang Park、Haichao Zhang、Michael D. Wendt、Aaron R. Kunzer、Andrew J. Souers、Chaohong Sun

  DOI：10.1016/j.bmcl.2014.02.010

  日期：2014.3

  Apoptosis is regulated by the BCL-2 family of proteins, which is comprised of both pro-death and pro-survival members. Evasion of apoptosis is a hallmark of malignant cells. One way in which cancer cells achieve this evasion is thru overexpression of the pro-survival members of the BCL-2 family. Overexpression of MCL-1, a pro-survival protein, has been shown to be a resistance factor for Navitoclax, a potent inhibitor of BCL-2 and BCL-XL. Here we describe the use of fragment screening methods and structural biology to drive the discovery of novel MCL-1 inhibitors from two distinct structural classes. Specifically, cores derived from a biphenyl sulfonamide and salicylic acid were uncovered in an NMR-based fragment screen and elaborated using high throughput analog synthesis. This culminated in the discovery of selective and potent inhibitors of MCL-1 that may serve as promising leads for medicinal chemistry optimization efforts.
• EP3593803
  申请人：——

  公开号：——

  公开（公告）日：——
• Dual IGF-1R/SRC inhibitors based on a N′-aroyl-2-(1H-indol-3-yl)-2-oxoacetohydrazide structure
  作者：Stefanie Schmidt、Lutz Preu、Thomas Lemcke、Frank Totzke、Christoph Schächtele、Michael H.G. Kubbutat、Conrad Kunick

  DOI：10.1016/j.ejmech.2011.03.065

  日期：2011.7

  The N'-aroyl-2-(1H-indol-3-yl)-2-oxoacetohydrazide motif was identified as a novel scaffold for the development of kinase inhibitors. Derivatives with a biphenyl element attached to the hydrazide structure proved to be submicromolar dual inhibitors of the cancer-related kinases IGF-1R and SRC. One of the most potent kinase inhibitors of the series produced a selective growth inhibition in a panel of cultivated cancer cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.