1-(甲苯-4-磺酰基)-1H-吲哚-3-硼酸频哪醇酯 | 1073354-51-4

• 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: 1-(甲苯-4-磺酰基)-1H-吲哚-3-硼酸频哪醇酯
• 中文别名: 3-（4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基）-1-甲苯基-1H-吲哚
• 英文名称: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indole
• 英文别名: 1-(4-methylphenyl)sulfonyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• CAS: 1073354-51-4
• 化学式: C₂₁H₂₄BNO₄S
• 分子量: 397.303
• InChiKey: KRZHRMGPJBEROU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,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: 1-(Toluene-4-sulfonyl)-1H-indole-3-boronic acid pinacol ester
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: 1-(Toluene-4-sulfonyl)-1H-indole-3-boronic acid pinacol ester
CAS number: 1073354-51-4

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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, under −20◦C.
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: C21H24BNO4S
Molecular weight: 397.3

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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, nitrogen oxides, 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：

  1-(甲苯-4-磺酰基)-1H-吲哚-3-硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-(5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)-6-isopropoxyisoindolin-5-amine trifluoroacetic acid
  参考文献：
  名称：

  嘧啶衍生物类间变性淋巴瘤激酶抑制剂

  摘要：

  本发明属于医药技术领域，具体涉及通式(Ⅰ)所示的嘧啶衍生物类间变性淋巴瘤激酶抑制剂或其立体异构体、或者其药学上可接受的盐、酯或溶剂化物，其中R1、R2、R3、R4、R5和A环如说明书中所定义。本发明还涉及这些化合物的制备方法，含有这些化合物的药物制剂和药物组合物，以及该化合物或其立体异构体、或者其药学上可接受的盐、酯或溶剂化物在制备治疗和/或预防由间变性淋巴瘤激酶介导的癌症相关疾病的药物中的应用。。

  公开号：

  CN104876914B
• 作为产物：
  描述：

  吲哚 在 四(三苯基膦)钯 、 碘 、 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 1-(甲苯-4-磺酰基)-1H-吲哚-3-硼酸频哪醇酯
  参考文献：
  名称：

  通过 Masuda Borylation-Suzuki Arylation (MBSA) 序列一锅法合成 Camalexins 和 3,3'-联吲哚

  摘要：

  从 N 保护的 3-碘吲哚开始的 Masuda 硼酸化/铃木芳基化 (MBSA) 序列已成功扩展到芳基化步骤中五元杂环和吲哚的偶联，这是以前开发的 MBSA 方法无法实现的。通过这种方法，该方法的一锅法特性以及简单催化剂体系的使用得到了保留。该方法的适用性已通过 camalexins 和 3,3'-联吲哚的轻松合成得到证明，这些化合物由于其显着的抗真菌、抗菌和细胞毒性活性而受到特别关注。

  DOI：

  10.1002/ejoc.201300133

文献信息

• Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters
  作者：Alexander M. Haydl、John F. Hartwig

  DOI：10.1021/acs.orglett.9b00025

  日期：2019.3.1

  method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities

  报道了一种使芳基，杂芳基和乙烯基硼酸酯直接甲基化的方法，该方法涉及碘甲烷与由钯和​​PtBu 2 Me催化的芳基，杂芳基和乙烯基硼酸酯的反应。这种转化发生的范围非常广，并且适合于通过硼酸酯进行生物活性化合物的后期衍生化。通过串联形成碳-硼键形成反应和钯催化的甲基化反应，证明了该方法的独特功能。
• Iridium(I)‐Catalyzed C−H Borylation in Air by Using Mechanochemistry
  作者：Yadong Pang、Tatsuo Ishiyama、Koji Kubota、Hajime Ito

  DOI：10.1002/chem.201900685

  日期：2019.3.27

  the first time to an iridium(I)‐catalyzed C−H borylation reaction. By using either none or just a catalytic amount of a liquid, the mechanochemical C−H borylation of a series of heteroaromatic compounds proceeded in air to afford the corresponding arylboronates in good‐to‐excellent yields. A one‐pot mechanochemical C−H borylation/Suzuki–Miyaura cross‐coupling sequence for the direct synthesis of 2‐aryl

  机械化学已首次应用于铱（I）催化的CH硼酸酯化反应。通过不使用或仅使用催化量的液体，一系列杂芳族化合物的机械化学CH硼化在空气中进行，从而以优异的产率获得了相应的芳基硼酸酯。还描述了直接合成2-芳基吲哚衍生物的一锅机械化学CH硼化/ Suzuki-Miyaura交叉偶联序列。这项研究是发展工业上有吸引力的无溶剂CH键在空气中的功能化过程的重要里程碑。
• 一种选择性针对细胞周期依赖性激酶12活性的化合物、制备方法及医药用途
  申请人：赛诺哈勃药业（成都）有限公司

  公开号：CN114133394A

  公开（公告）日：2022-03-04

  本说明书提供了具有化学式(I)的化合物，或其药学上可接受的盐、氘代化合物、互变异构体、顺反异构体、内消旋体、外消旋体、对映异构体、非对映异构体或其混合物，用于制备此类化合物的方法，以及此类化合物用于调节或是抑制细胞周期依赖性激酶(Cyclin‑dependent kinases，CDKs)的活性并且用于治疗和预防与CDKs活性相关的疾病的用途。
• Nature-Inspired (di)Azine-Bridged Bisindole Alkaloids with Potent Antibacterial <i>In Vitro</i> and <i>In Vivo</i> Efficacy against Methicillin-Resistant <i>Staphylococcus aureus</i>
  作者：Nidja Rehberg、Gereon A. Sommer、Daniel Drießen、Marco Kruppa、Emmanuel T. Adeniyi、Shang Chen、Lin Wang、Karina Wolf、Boris O. A. Tasch、Thomas R. Ioerger、Kui Zhu、Thomas J. J. Müller、Rainer Kalscheuer

  DOI：10.1021/acs.jmedchem.0c00826

  日期：2020.11.12

  highly active against methicillin-resistant Staphylococcus aureus (MRSA) and further Gram-positive pathogens at minimal inhibitory concentrations ranging from 0.20 to 0.78 μM. These compounds showed strong bactericidal killing effects but only moderate cytotoxicity against human cell lines. Furthermore, the two front-runner compounds 4j and 4n exhibited potent in vivo efficacy against MRSA in a mouse

  天然双吲哚生物碱，如Hyrtinadine A和Alocasin A，已知具有多种生物活性，它们为药物开发提供了有希望的化学支架。通过优化Masuda的borylation–Suzuki偶联序列，创建了各种天然产物衍生的和非天然（二）嗪桥联的双吲哚的文库。尽管未取代的双吲哚没有抗菌活性，但5,5'-氯衍生物在最小抑菌浓度范围为0.20至0.78μM时对耐甲氧西林的金黄色葡萄球菌（MRSA）和其他革兰氏阳性病原体具有高活性。这些化合物显示出很强的杀菌作用，但对人细胞系仅具有中等的细胞毒性。此外，两个领先的化合物4j和4n在小鼠伤口感染模型中显示出针对MRSA的有效体内功效。尽管据报道结构相关的双吲哚专门针对MRSA中的丙酮酸激酶，但4j和4n的抗菌活性与丙酮酸激酶无关。而是，这些化合物导致细菌膜通透性和低分子量分子的细胞外排。
• Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF₃
  作者：Shitao Pan、Qiqiang Xie、Xiu Wang、Qian Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/d2cc00975g

  日期：——

  The TMSCF₃-derived CuCF₂CF₃ species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes.

  TMSCF3衍生的CuCF2CF3物种已成功应用于有机硼酸酯和末端炔烃的五氟乙基化反应。