4-羧基-3-氟苯基硼酸频哪醇酯 | 867256-77-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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: 4-羧基-3-氟苯基硼酸频哪醇酯
• 中文别名: 4-羧基-3-氟苯硼酸频那醇酯；3-羧基-4-氟苯基硼酸频哪醇酯；4-羧基-3-氟苯硼酸频哪酯
• 英文名称: 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
• 英文别名: 4-carboxy-3-fluorophenylboronic acid pinacol ester
• CAS: 867256-77-7
• 化学式: C₁₃H₁₆BFO₄
• 分子量: 266.077
• InChiKey: BZWWFDHWZHGLFH-UHFFFAOYSA-N

物化性质

• 熔点：
  289-295℃
• 沸点：
  377.6±32.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,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-Carboxy-3-fluorophenylboronic acid, pinacol ester
Synonyms: 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

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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-Carboxy-3-fluorophenylboronic acid, pinacol ester
CAS number: 867256-77-7

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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.
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: C13H16BFO4
Molecular weight: 266.1

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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, 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：

  4-羧基-3-氟苯基硼酸频哪醇酯 在 四(三苯基膦)钯 、 potassium phosphate monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 2-[(5S)-2-[4-(3,3-difluoropyrrolidine-1-carbonyl)-3-fluorophenyl]-5H-chromeno[2,3-b]pyridin-5-yl]-N-[(4-methoxyphenyl)methylcarbamoyl]-2-methylpropanamide
  参考文献：
  名称：

  [EN] IMIDE AND ACYLUREA DERIVATIVES AS MODULATORS OF THE GLUCOCORTICOID RECEPTOR
  [FR] DÉRIVÉS IMIDE ET ACYLURÉE UTILISÉS COMME MODULATEURS DU RÉCEPTEUR DE GLUCOCORTICOÏDES

  摘要：

  提供了一种新型的非类固醇化合物，可用于治疗与糖皮质激素受体、AP-1和/或NF-KB活性调节相关的疾病或紊乱，包括代谢性、炎症性和免疫性疾病或紊乱，其结构如下式（I）：其对映体、二对映体或互变异构体，或其药用可接受盐，其中变量如规范中所定义。

  公开号：

  WO2015027021A1
• 作为产物：
  描述：

  4-羧基-3-氟苯硼酸 、 频哪醇 在 甲苯 作用下， 以 toluene ethanol 为溶剂， 反应 16.0h， 以to give 1.42 g的产率得到4-羧基-3-氟苯基硼酸频哪醇酯
  参考文献：
  名称：

  HISTAMINE H3 RECEPTOR AGENTS, PREPARATION AND THERAPEUTIC USES

  摘要：

  本发明披露了公式（I）的新化合物或其药学上可接受的盐，具有组胺H3受体拮抗剂或反向激动剂活性，以及制备这些化合物的方法。在另一种实施方式中，本发明披露了包含公式（I）化合物的制药组合物，以及使用它们治疗肥胖症、认知缺陷、嗜睡病和其他组胺H3受体相关疾病的方法。

  公开号：

  US20070208024A1

文献信息

• [EN] HISTAMINE H3 RECEPTOR AGENTS, PREPARATION AND THERAPEUTIC USES<br/>[FR] AGENTS RECEPTEURS DE L'HISTAMINE H3, PREPARATION ET UTILISATIONS THERAPEUTIQUES
  申请人：LILLY CO ELI

  公开号：WO2005097740A1

  公开（公告）日：2005-10-20

  The present invention discloses novel compounds of Formula (I) or pharmaceutically acceptable salts thereof, which have histamine-H3 receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of using them to treat obesity, cognitive deficiencies, narcolepsy, and other histamine H3 receptor-related diseases

  本发明公开了具有组合物(I)或其药学上可接受的盐的新颖化合物，其具有组胺H3受体拮抗剂或逆激动剂活性，以及制备这种化合物的方法。在另一实施例中，本发明公开了包含组合物(I)的药物组合物，以及使用它们治疗肥胖、认知缺陷、嗜睡症和其他组胺H3受体相关疾病的方法。
• [EN] NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES<br/>[FR] NOUVEAUX COMPOSÉS UTILES POUR LE TRAITEMENT DE MALADIES DÉGÉNÉRATIVES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2010010186A1

  公开（公告）日：2010-01-28

  [1,2,4]Triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: (I) These compound may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  [1,2,4]三唑并[1,5-a]吡啶化合物被披露，其具有以下公式(I)表示的化合物。这些化合物可以制备成药物组合物，并且可以用于预防和治疗包括人类在内的哺乳动物的多种病症，包括但不限于涉及软骨降解、骨骼和/或关节退化的疾病，例如骨关节炎；以及/或涉及炎症或免疫反应的状况，如克罗恩病、类风湿性关节炎、银屑病、过敏性呼吸道疾病（例如哮喘、鼻炎）、幼年特发性关节炎、结肠炎、炎症性肠病、内毒素驱动的疾病状态（例如搭桥手术后的并发症或慢性内毒素状态导致慢性心力衰竭）、涉及软骨转换受损的疾病（例如涉及软骨细胞合成代谢刺激的疾病）、先天性软骨畸形、与IL6过度分泌和移植排斥反应相关的疾病（例如器官移植排斥）以及增殖性疾病。
• Application of a Parallel Synthetic Strategy in the Discovery of Biaryl Acyl Sulfonamides as Efficient and Selective Na_V1.7 Inhibitors
  作者：Erin F. DiMauro、Stephen Altmann、Loren M. Berry、Howard Bregman、Nagasree Chakka、Margaret Chu-Moyer、Elma Feric Bojic、Robert S. Foti、Robert Fremeau、Hua Gao、Hakan Gunaydin、Angel Guzman-Perez、Brian E. Hall、Hongbing Huang、Michael Jarosh、Thomas Kornecook、Josie Lee、Joseph Ligutti、Dong Liu、Bryan D. Moyer、Daniel Ortuno、Paul E. Rose、Laurie B. Schenkel、Kristin Taborn、Jean Wang、Yan Wang、Violeta Yu、Matthew M. Weiss

  DOI：10.1021/acs.jmedchem.6b00425

  日期：2016.9.8

  a parallel synthetic approach was applied to rapidly generate the derived acyl sulfonamides. A biaryl acyl sulfonamide hit from this library was elaborated, optimizing for potency and selectivity with attention to physicochemical properties. The resulting novel leads are potent, ligand and lipophilic efficient, and selective over hNaV1.5. Representative lead 36 demonstrates selectivity over other human

  大多数有效的和选择性的hNa V 1.7抑制剂具有常见的药理学特征，包括杂芳基磺酰胺头基和亲脂性芳族尾基。最近，已经出现了类似的芳香族尾基与酰基磺酰胺头基结合的报道，酰基磺酰胺赋予了相对于hNa V的选择性水平1.5与杂芳基磺酰胺相当。从满足亲脂性尾部中选定药理学要求的市售羧酸开始，采用平行合成方法快速生成衍生的酰基磺酰胺。精心制作了该文库中的联芳基酰基磺酰胺，优化了效价和选择性，并关注了理化性质。所得的新的铅是有效的，配体和亲脂性的，并且在hNa V 1.5上具有选择性。代表性的铅36证明了在鼠类中对其他人类Na V同工型的选择性和良好的药代动力学。与已知的杂芳基磺酰胺抑制剂相比，本文报道的联芳基酰基磺酰胺还可以提供ADME优势。
• Efficient Synthesis of Boron-Containing α-Acyloxyamide Analogs via Microwave Irradiation
  作者：Chih-Cheng Chai、Pin-Yi Liu、Chia-Hung Lin、Hsien-Chi Chen、Yang-Chang Wu、Fang-Rong Chang、Po-Shen Pan

  DOI：10.3390/molecules18089488

  日期：——

  three-component reaction utilizing boron-containing carboxylic acids or aldehydes is discussed. The reaction was carried out in water and facilitated by the use of microwave irradiation. This methodology allowed for the efficient formation of a broad range of boron-containing α-acyloxyamides under mild conditions within a short time. Two series of boron-containing α-acyloxyamides were synthesized and

  在本报告中，讨论了利用含硼羧酸或醛的 Passerini 三组分反应。该反应在水中进行并通过使用微波辐射来促进。这种方法允许在短时间内在温和条件下有效形成范围广泛的含硼 α-酰氧基酰胺。合成了两个系列的含硼 α-酰氧基酰胺，随后使用 MTT 细胞活力测定筛选了细胞毒性。发现两种潜在的先导化合物对 HepG2 癌细胞系具有强效活性，证明了这种方法在开发新型药物方面的潜力。
• [EN] DIOL-MODIFIED INSULIN ANALOGUES CONTAINING A GLUCOSE-REGULATED CONFORMATIONAL SWITCH<br/>[FR] ANALOGUES DE L'INSULINE MODIFIÉS AVEC UN DIOL CONTENANT UN COMMUTATEUR DE CONFORMATION RÉGULÉ PAR LE GLUCOSE
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2017070617A1

  公开（公告）日：2017-04-27

  An insulin analogue contains a specific combination of modifications to the A- and B chains: (i) a phenylboronic acid derivative (optionally including a halogen atom substitution) linked by a connecting element either to the alpha-amino group of GlyA1, to the epsilon-amino group of non-standard variant D-LysA1, to the epsilon-amino group of standard variant L-LysA4, to the alpha-amino group of D-LysA1 and its epsilon-amino group, to the alpha-amino group of GlyA1 and the epsilon-amino group of L-LysA4, or to any combination of the above three sites; and (ii) one, two or three diol-containing adducts linked to side chains in the wild-type or variant B27-B30 segment, or within a one-residue C-terminal extension of the B chain (B31) or within a two-residue extension of the B chain (B31-B32). A method of treating a patient comprises administration of an effective amount of the insulin analogue or a physiologically acceptable salt thereof to a patient.

  一种胰岛素类似物包含特定的A链和B链修饰组合：(i)一种苯基硼酸衍生物（可包括卤素原子替代），通过连接元素连接到GlyA1的α-氨基基团，非标准变异体D-LysA1的ε-氨基基团，标准变异体L-LysA4的ε-氨基基团，D-LysA1和其ε-氨基基团的α-氨基基团，GlyA1的α-氨基基团和L-LysA4的ε-氨基基团，或以上三个位点的任意组合；(ii)一个、两个或三个含二醇的加合物，连接到野生型或变异型B27-B30段的侧链，或B链的一个氨基酸C端扩展（B31）或B链的两个氨基酸扩展（B31-B32）中。一种治疗患者的方法包括向患者施用胰岛素类似物或其生理上可接受的盐的有效量。