4-三氟甲基硫代苯硼酸频那醇酯 | 1005206-25-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 4-三氟甲基硫代苯硼酸频那醇酯
• 中文别名: 三氟甲硫基-4-（4,4,5,5-四甲基-[1,3,2]二氧杂硼烷-2-基）-苯
• 英文名称: 4,4,5,5-tetramethyl-2-(4-((trifluoromethyl)thio)phenyl)-1,3,2-dioxaborolane
• 英文别名: 2-(4-((trifluoromethyl)thio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-[4-(trifluoromethylsulfanyl)phenyl]-1,3,2-dioxaborolane
• CAS: 1005206-25-6
• 化学式: C₁₃H₁₆BF₃O₂S
• 分子量: 304.141
• InChiKey: RSMWGZJSATWLMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P270,P273,P301+P312,P330
• 危险性描述：
  H302,H413

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-trifluoromethylthiophenylboronic acid pinacol ester
Synonyms: Trifluoromethylthio-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene

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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-trifluoromethylthiophenylboronic acid pinacol ester
CAS number: 1005206-25-6

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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: C13H16BF3O2S
Molecular weight: 304.1

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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, sulfur oxides.

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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：

  4-三氟甲基硫代苯硼酸频那醇酯 在 sodium periodate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.5h， 以73%的产率得到4-哌啶并唑,1-(4,6-二氨基-1,3,5-三嗪-2-基)-
  参考文献：
  名称：

  [EN] ARYL-HYDROXYETHYLAMINO-PYRIMIDINES AND TRIAZINES AS MODULATORS OF FATTY ACID AMIDE HYDROLASE
  [FR] ARYL-HYDROXYÉTHYLAMINO-PYRIMIDINES ET TRIAZINES EN TANT QUE MODULATEURS D'AMIDE D'ACIDE GRAS HYDROLASE

  摘要：

  描述了某些芳基-羟乙基氨基嘧啶和三嗪化合物，这些化合物可用作FAAH抑制剂。这些化合物可用于制备药物组合物和治疗由脂肪酸酰胺水解酶（FAAH）活性介导的疾病状态、紊乱和症状，如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢障碍和运动障碍（例如多发性硬化）。还公开了合成这些化合物的方法。

  公开号：

  WO2009105220A1
• 作为产物：
  描述：

  对三氟甲硫基苯甲酸 在 4-二甲氨基吡啶 、 4-(叔丁氧羰基)吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 反应 17.0h， 生成 4-三氟甲基硫代苯硼酸频那醇酯
  参考文献：
  名称：

  N-羟基邻苯二甲酰亚胺酯对异烟酸酯的催化（杂）芳基和烯基羧酸的脱羧硼化反应

  摘要：

  芳基和链烯基羧酸与双（频哪醇合）二硼的脱羧硼化通过实现Ñ使用-hydroxyphthalimide酯叔异烟酸丁酯在无碱条件下作为催化剂。可以将具有不同官能团和电子特性的各种芳基羧酸平稳地转化为芳基硼酸酯，包括在过渡金属催化下难以脱羧的芳基硼酸酯，从而提供了一种新方法，使羧酸可以用作有机合成中的基础。机理分析表明，该反应通过自由基脱羧产生的瞬态芳基与吡啶稳定的持久性硼基的偶联而进行。氧化还原活性酯的活化可以通过分子内单电子转移（SET）过程，通过吡啶-二硼-邻苯二甲酰亚胺加合物进行，并说明了无碱反应条件。

  DOI：

  10.1021/acs.orglett.7b01950

文献信息

• Target Elucidation by Cocrystal Structures of NADH-Ubiquinone Oxidoreductase of <i>Plasmodium falciparum</i> (<i>Pf</i>NDH2) with Small Molecule To Eliminate Drug-Resistant Malaria
  作者：Yiqing Yang、You Yu、Xiaolu Li、Jing Li、Yue Wu、Jie Yu、Jingpeng Ge、Zhenghui Huang、Lubin Jiang、Yu Rao、Maojun Yang

  DOI：10.1021/acs.jmedchem.6b01733

  日期：2017.3.9

  Drug-resistant malarial strains have been continuously emerging recently, which posts a great challenge for the global health. Therefore, new antimalarial drugs with novel targeting mechanisms are urgently needed for fighting drug-resistant malaria. NADH-ubiquinone oxidoreductase of Plasmodium falciparum (PfNDH2) represents a viable target for antimalarial drug development. However, the absence of

  最近，耐药性疟疾菌株不断出现，这对全球健康构成了巨大挑战。因此，迫切需要具有新颖靶向机制的新抗疟药来对抗耐药性疟疾。恶性疟原虫的NADH-泛醌氧化还原酶（Pf NDH2）代表了抗疟疾药物开发的可行目标。但是，缺乏有关Pf NDH2的结构信息限制了合理的药物设计和进一步的开发。在这里，我们首次报道了Af-，NADH-和RYL-552（一种新的抑制剂）结合状态的Pf NDH2蛋白的高分辨率晶体结构。该Pf的NDH2抑制剂通过潜在的变构机制，对体外耐药菌和体内寄生虫感染的小鼠均表现出出色的效力。此外，发现该抑制剂可以与二氢青蒿素（DHA）协同地结合使用。这些发现不仅对于基于疟疾Pf NDH2蛋白的药物开发很重要，而且对其他含有NDH2的致病微生物（如结核分枝杆菌）也可能具有广泛的意义。
• Discovery, Optimization, and Target Identification of Novel Potent Broad-Spectrum Antiviral Inhibitors
  作者：Yiqing Yang、Lin Cao、Hongying Gao、Yue Wu、Yaxin Wang、Fang Fang、Tianlong Lan、Zhiyong Lou、Yu Rao

  DOI：10.1021/acs.jmedchem.9b00091

  日期：2019.4.25

  exploited by phenotypic screening to discover new antiviral inhibitors. After optimizations from hit to lead, a novel potent small molecule (RYL-634) was identified, showing excellent broad-spectrum inhibition activity against various pathogenic viruses, including hepatitis C virus, dengue virus, Zika virus, chikungunya virus, enterovirus 71, human immunodeficiency virus, respiratory syncytial virus

  病毒感染正在增加，并且可能是持久的全球风险。在这项研究中，通过表型筛选开发了一个化学文库，以发现新的抗病毒抑制剂。经过从头到尾的优化后，鉴定出一种新型的强效小分子（RYL-634），它对各种致病性病毒（包括丙型肝炎病毒，登革热病毒，寨卡病毒，基孔肯雅病毒，肠病毒71，人免疫缺陷病毒，呼吸道合胞病毒等。通过结合基于活性的蛋白质谱分析和其他技术，进一步探索了RYL-634的作用机理和潜在靶标。最后，人二氢乳清酸酯脱氢酶被证实是RYL-634的主要靶标。在使用RYL-634进行压力选择时，我们没有观察到任何突变抗性，并且与某些获得美国食品药品监督管理局（FDA）批准的药物具有很强的协同作用。因此，有很大的潜力开发基于RYL-634的新型广谱抗病毒药。
• GSK-3BETAINHIBITOR
  申请人：Itoh Fumio

  公开号：US20100069381A1

  公开（公告）日：2010-03-18

  For the purpose of providing a GSK-3β inhibitor containing an oxadiazole compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.

  为了提供一种含有噁二唑化合物或其盐或其前药的GSK-3β抑制剂，用作GSK-3β相关病理或疾病的预防或治疗剂，本发明提供了一种含有由以下式（I）表示的化合物的GSK-3β抑制剂： 其中每个符号如规范中定义，或其盐或其前药。
• [EN] ARYL-HYDROXYETHYLAMINO-PYRIMIDINES AND TRIAZINES AS MODULATORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] ARYL-HYDROXYÉTHYLAMINO-PYRIMIDINES ET TRIAZINES EN TANT QUE MODULATEURS D'AMIDE D'ACIDE GRAS HYDROLASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009105220A1

  公开（公告）日：2009-08-27

  Certain aryl-hydroxyethylamino-pyrimidine and triazine compounds are described, which are useful as FAAH inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by fatty acid amide hydrolase (FAAH) activity, such as anxiety, pain, inflammation, sleep disorders, eating disorders, energy metabolism disorders, and movement disorders (e.g., multiple sclerosis). Methods of synthesizing such compounds are also disclosed.

  描述了某些芳基-羟乙基氨基嘧啶和三嗪化合物，这些化合物可用作FAAH抑制剂。这些化合物可用于制备药物组合物和治疗由脂肪酸酰胺水解酶（FAAH）活性介导的疾病状态、紊乱和症状，如焦虑、疼痛、炎症、睡眠障碍、进食障碍、能量代谢障碍和运动障碍（例如多发性硬化）。还公开了合成这些化合物的方法。
• [EN] BRIDGED PIPERIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PIPÉRIDINE PONTÉS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017042114A1

  公开（公告）日：2017-03-16

  The present invention relates to compounds of formula (I); hetaryl is a five membered heteroaryl group, containing 1 to 3 heteroatoms, selected from O, S or N; R1 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkyl substituted by halogen, S-lower alkyl substituted by halogen or lower alkoxy substituted by halogen, or two neighboring carbon atoms may form on phenyl an additional ring containing -O-CH2-O-; n is 1 to 5; R2 is hydrogen or lower alkyl substituted by halogen; R3 is hydrogen or lower alkyl substituted by halogen; or to pharmaceutically active acid addition salts thereof, to racemic mixtures or to its corresponding enantiomers or optical isomers or stereoisomers thereof. The compounds may be used for the treatment of Alzheimer's disease, cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi-infarct dementia, dementia pugilistica or Down syndrome.

  本发明涉及式(I)的化合物；hetaryl是一个含有1至3个杂原子（O、S或N）的五元杂芳基团；R1是氢、卤素、低碳链烷基、低碳链烷氧基、被卤素取代的低碳链烷基、被卤素取代的S-低碳链烷基或被卤素取代的低碳链烷氧基，或者邻近的两个碳原子可在苯基上形成一个含有-O-CH2-O-的额外环；n为1至5；R2是氢或被卤素取代的低碳链烷基；R3是氢或被卤素取代的低碳链烷基；或其药用酸加合物、消旋混合物、对映体或光学异构体或立体异构体。这些化合物可用于治疗阿尔茨海默病、脑淀粉样血管病、遗传性脑出血伴淀粉样病变的荷兰型（HCHWA-D）、多梗塞性痴呆、拳击性痴呆或唐氏综合征。