4-羧基-3-甲基苯硼酸频那醇酯 | 890839-22-2

• 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-甲基苯硼酸频那醇酯
• 中文别名: 4-羧-3-甲基苯基硼酸频哪醇酯
• 英文名称: 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid
• 英文别名: 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoic acid
• CAS: 890839-22-2
• 化学式: C₁₄H₁₉BO₄
• 分子量: 262.113
• InChiKey: OOIMFYJDAOJRFA-UHFFFAOYSA-N

物化性质

• 沸点：
  396.6±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Carboxy-3-methylphenylboronic acid, pinacol ester
Synonyms: 2-Methyl-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-methylphenylboronic acid, pinacol ester
CAS number: 890839-22-2

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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: C14H19BO4
Molecular weight: 262.1

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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：

  4-羧基-3-甲基苯硼酸频那醇酯 、 3-bromo-5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 8.0h， 以84%的产率得到4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid
  参考文献：
  名称：

  异噁唑化合物的制备

  摘要：

  本发明涉及氟雷拉纳及其类似物的制备方法。具体为1‑取代‑3‑取代‑5‑(3,3,3‑三氟丙‑烯‑2‑基)苯和1,1‑二溴甲醛肟发生反应制备得到3‑溴‑5‑(3‑取代‑5‑取代‑苯基)‑5‑(三氟甲基)‑4,5‑二氢异噁唑；3‑溴‑5‑(3‑取代‑5‑取代‑苯基)‑5‑(三氟甲基)‑4,5‑二氢异噁唑和2‑甲基‑4‑(4,4,5,5‑四甲基‑1,3‑二氧戊环‑2‑基)苯甲酸发生反应，制备得到4‑(5‑(3‑取代‑5‑取代‑苯基)‑5‑(三氟甲基)‑4,5‑二氢异噁唑‑3‑基)‑2‑甲基苯甲酸；4‑(5‑(3‑取代‑5‑取代‑苯基)‑5‑(三氟甲基)‑4,5‑二氢异噁唑‑3‑基)‑2‑甲基苯甲酸和2‑氨基‑N‑(2,2,2‑三氟乙基)乙酰胺盐酸盐发生反应，制备得到氟雷拉纳及其类似物。

  公开号：

  CN114591259A
• 作为产物：
  描述：

  4-溴-2-甲基苯甲酸 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 4-羧基-3-甲基苯硼酸频那醇酯
  参考文献：
  名称：

  开发基于 TCMDC-135051 的强效 PfCLK3 抑制剂作为新型抗疟药。

  摘要：

  蛋白激酶Pf CLK3 在疟原虫 RNA 剪接的调节中起关键作用，对恶性疟原虫的血期生存至关重要。我们最近验证了Pf CLK3 作为疟疾的药物靶点，具有预防、阻断传播和治疗的潜力。在这里，我们描述了我们最初的热门 TCMDC-135051 (1)的合成以及与基于 7-氮杂吲哚的系列建立结构-活性关系的努力。在针对全长重组蛋白激酶Pf CLK3 的时间分辨荧光能量转移测定中评估了总共 14 种类似物，并在无性 3D7（氯喹敏感）菌株中进一步评估了 11 种类似物。恶性疟原虫寄生虫。建立了与 A 环和 B 环相关的 SAR。这些数据连同从该领域的患者中收集的针对寄生虫的活性分析表明，TCMDC-135051 (1)是一种很有前途的先导化合物，可用于开发具有针对Pf CLK3的新作用机制的新型抗疟药。

  DOI：

  10.1021/acs.jmedchem.0c00451

文献信息

• Novel 3 H -[1,2,3]triazolo[4,5- c ]pyridine derivatives as GPR119 agonists: Synthesis and structure-activity/solubility relationships
  作者：Daisuke Matsuda、Yohei Kobashi、Ayako Mikami、Madoka Kawamura、Fumiyasu Shiozawa、Kenichi Kawabe、Makoto Hamada、Shinichi Nishimoto、Kayo Kimura、Masako Miyoshi、Noriko Takayama、Hiroyuki Kakinuma、Norikazu Ohtake

  DOI：10.1016/j.bmc.2017.06.014

  日期：2017.8

  We previously reported a novel series of 1H-pyrazolo[3,4-c]pyridine derivatives and the identification of compound 4b as a highly potent GPR119 agonist. However, the advancement of preclinical evaluations of compound 4b is expected to be difficult because of the compound’s significantly poor aqueous solubility (0.71 μM at pH6.8). In this article, we describe the further optimization of compound 4b

  我们先前报道了一系列新型的1 H-吡唑并[3,4- c ]吡啶衍生物，并将化合物4b鉴定为高效GPR119激动剂。但是，由于该化合物的水溶性差（在pH6.8下为0.71μM），因此很难进行化合物4b的临床前评估。在本文中，我们描述了化合物4b的进一步优化，重点是提高其水溶性。优化中央间隔基，左手的芳基和右手的哌啶N-封端基团导致鉴定出强效的GPR119激动剂3 H- [1,2,3]三唑[4,5- c ]]吡啶衍生物32o，具有改善的溶解度（在pH6.8下为15.9μM）。
• [EN] TOLL-LIKE RECEPTOR 8 (TLR8)-SPECIFIC ANTAGONISTS AND METHODS OF MAKING AND USES THEREOF<br/>[FR] ANTAGONISTES SPÉCIFIQUES DU RÉCEPTEUR DE TYPE TOLL 8 ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION ASSOCIÉS
  申请人：UNIV COLORADO REGENTS

  公开号：WO2019089648A1

  公开（公告）日：2019-05-09

  Toll-like receptor 8 (TLR8)-specific inhibitors and methods of using the same in individuals having an autoimmune disease or an inflammatory disorder.

  Toll样受体8(TLR8)-特异性抑制剂及其在患有自身免疫疾病或炎症性疾病个体中的使用方法。
• SUBSTITUTED IMIDAZOPYRIDAZINES
  申请人：Klar Ulrich

  公开号：US20130338133A1

  公开（公告）日：2013-12-19

  The present invention relates to substituted imidazopyridazine compounds of general formula (I), which are Mps-1 (Monopolar Spindle 1) Kinase inhibitors (also known as Tyrosine Threonine Kinase, TTK) in which R 3 , R 5 , and A are as defined in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyper-proliferative and/or angiogenesis disorder, as a sole agent or in combination with other active ingredients.

  本发明涉及一般式（I）的取代咪唑吡啶基化合物，它们是Mps-1（单极纺锤体1）激酶抑制剂（也称为酪氨酸苏氨酸激酶，TTK），其中R3，R5和A如权利要求所定义，以制备这些化合物的方法，包括所述化合物的制药组合物和配伍物，以及使用所述化合物制造用于治疗或预防疾病的制药组合物，特别是用作单一剂量或与其他活性成分联合使用，用于治疗或预防过度增生和/或血管生成障碍。
• Substituted imidazopyridazines
  申请人：Klar Ulrich

  公开号：US09255100B2

  公开（公告）日：2016-02-09

  The present invention relates to substituted imidazopyridazine compounds of general formula (I), which are Mps-1 (Monopolar Spindle 1) Kinase inhibitors (also known as Tyrosine Threonine Kinase, TTK) in which R3, R5, and A are as defined in the claims, to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyper-proliferative and/or angiogenesis disorder, as a sole agent or in combination with other active ingredients.

  本发明涉及通式（I）的取代咪唑吡啶烷化合物，其是Mps-1（单极纺锤体1）激酶抑制剂（也称为酪氨酸苏氨酸激酶，TTK），其中R3、R5和A如权利要求中所定义，以及制备这些化合物的方法，包括含有这些化合物的药物组合物和制造用于治疗或预防疾病，特别是增生和/或血管生成障碍的药物组合物的方法，作为单一药剂或与其他活性成分联合使用。
• 一种异噁唑啉类衍生物的制备方法
  申请人：武汉工程大学

  公开号：CN114957147A

  公开（公告）日：2022-08-30

  本发明涉及农药化学技术领域，尤其涉及一种异噁唑啉类衍生物的制备方法。所述异噁唑啉类衍生物为弗雷拉纳，所述弗雷拉纳的化学结构式如通式Ⅰ所示：制备所述弗雷拉纳的具体反应步骤如下：步骤A：将化合物e、化合物d和碱一加入到溶剂一中进行关环反应，制得中间体Ⅰ；步骤B：将中间体Ⅰ、化合物c、碱二和催化剂加入到溶剂二中进行Suzuki‑Miyaura反应，制得中间体Ⅱ；步骤C：将中间体Ⅱ、化合物b、碱三和缩合剂加入到溶剂三中进行酰胺化缩合反应，即得弗雷拉纳。本发明的制备方法制得的弗雷拉纳的产率高，整个制备过程中产生的杂质少，有利于弗雷拉纳的产业化合成生产，降低生产成本，提升弗雷拉纳的市场竞争力。