5-异丙基-2-甲氧基苯硼酸 | 216393-63-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 5-异丙基-2-甲氧基苯硼酸
• 英文名称: (5-isopropyl-2-methoxyphenyl)boronic acid
• 英文别名: 5-isopropyl-2-methoxybenzeneboronic acid；5-Isopropyl-2-methoxyphenylboronic acid；(2-methoxy-5-propan-2-ylphenyl)boronic acid
• CAS: 216393-63-4
• 化学式: C₁₀H₁₅BO₃
• mdl: MFCD01318154
• 分子量: 194.038
• InChiKey: UTKAEAGLVJFBMK-UHFFFAOYSA-N

物化性质

• 熔点：
  84-88 °C
• 沸点：
  350.0±52.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Isopropyl-2-methoxyphenylboronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
5-Isopropyl-2-methoxyphenylboronic acid
Ingredient name:
CAS number: 216393-63-4

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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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H15BO3
Molecular weight: 194.0

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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.

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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：

  5-异丙基-2-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[2-(dimethylamino)ethyl]-N'-(5-(5-isopropyl-2-methoxyphenyl)-2-pyrimidinyl)-N-methylphenyl-1,4-diamine
  参考文献：
  名称：

  基于 2-氨基嘧啶的 LSD1 抑制剂的设计、合成和生物学评价

  摘要：

  AZD9291具有优良的药学特性，据报道具有一定的LSD1抑制活性。因此，我们基于AZD9291骨架进行了结构优化，以增加化合物的LSD1抑制潜力。然后，设计并合成了一系列2-氨基嘧啶衍生物作为LSD1抑制剂，并研究了它们的构效关系。最有希望的化合物X43的 IC 50为 0.89 μM，不仅对 EGFR wt（>100 倍）而且对 MAO-A/B（>50 倍）显示出显着的 LSD1 选择性。进一步的研究表明，X43以剂量依赖性方式抑制 LSD1 活性并诱导 A549 细胞凋亡。同时，化合物X43显示出优异的抑制A549和THP-1细胞增殖的能力，IC 50值分别为1.62 μM和1.21 μM。然后，对人肝微粒体的稳定性、CYP 抑制和大鼠体内药代动力学的分析表明，X43在体外和体内具有良好的特性，并具有进一步研究的潜力。我们的研究结果表明，基于 2-氨基嘧啶的 LSD1 抑制剂值得进一步研究作为

  DOI：

  10.1016/j.bioorg.2022.105699
• 作为产物：
  描述：

  2-bromo-4-isopropylanisole 在 正丁基锂 、 triisopropyl borate 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 5-异丙基-2-甲氧基苯硼酸
  参考文献：
  名称：

  New 5-Aryl-1H-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting

  摘要：

  We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 mu M to single digit mu M. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.

  DOI：

  10.1021/jm400287v
• 作为试剂：
  描述：

  β-四氢萘酮 、 N,N-二甲基甲酰胺 在 5-异丙基-2-甲氧基苯硼酸 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  新型带有环烯烃骨架的胆固醇酯转移蛋白抑制剂的设计，合成和生物学评价

  摘要：

  胆固醇酯转移蛋白（CETP）是心血管疾病治疗的潜在目标，因为抑制CETP会导致人类HDL-C升高。基于Merck的联苯CETP抑制剂的结构，我们利用核心置换和构象限制策略设计了新型的N，N-取代的环烯基-甲胺骨架衍生物。因此，合成了28种化合物并评估了其对CETP的抑制活性。他们的初步结构-活性关系（SARs）研究表明，极性取代基在A部分中具有耐受性，而环己烯5-位的疏水烷基对效能至关重要。其中，化合物17a带有N-（5-吡唑基-嘧啶-2-基）-环烯基-甲胺支架在体外表现出出色的CETP抑制活性（IC 50  = 0.07μM）。此外，它在SD大鼠中显示出可接受的药代动力学特征，在高脂喂养的仓鼠中有效地增加了HDL-C。

  DOI：

  10.1016/j.ejmech.2016.07.065

文献信息

• Directing Group‐Promoted Inert C−O Bond Activation Using Versatile Boronic Acid as a Coupling Agent
  作者：Ram Ambre、Ting‐Hsuan Wang、Anmei Xian、Yu‐Shiuan Chen、Yu‐Fu Liang、Titel Jurca、Lili Zhao、Tiow‐Gan Ong

  DOI：10.1002/chem.202004132

  日期：2020.12.18

  strategy facilitates the efficient catalytic cross‐coupling of methoxyarenes with a variety of organoboron reagents. Directing groups facilitate the activation of inert C−O bonds in under‐utilized aryl methyl ethers enabling their adaptation for C−C cross‐coupling reactions as less toxic surrogates to the ubiquitous haloarenes. The method reported enables C−C cross‐coupling with readily available and economical

  一个简单的Ni（cod）2卡宾介导的策略促进了甲氧基芳烃与多种有机硼试剂的高效催化交叉偶联。定向基团可促进未充分利用的芳基甲基醚中惰性C-O键的活化，使它们能够适应C-C交叉偶联反应，因为对普遍存在的卤代芳烃的毒性较小。报道的方法可以使C-C与现成的经济型芳基硼酸试剂进行交叉偶联，这是前所未有的，并且可以与具有类似高反应活性的其他有机硼试剂进行比较。据报道，扩展了引导基团辅助的化学选择性的C-O键裂解，并进一步应用于合成新型双官能联芳基。
• SARs for the Antiparasitic Plant Metabolite Pulchrol. Part 2: B- and C-Ring Substituents
  作者：Paola Terrazas、Sophie Manner、Olov Sterner、Marcelo Dávila、Alberto Giménez、Efrain Salamanca

  DOI：10.3390/molecules25194510

  日期：——

  research on the plant metabolite pulchrol, a natural benzochromene which has been shown to possess antiparasitic activity against Trypanosoma and Leishmania species. In a recent study, we investigated how changes in the benzyl alcohol functionality affected the antiparasitic activity, but the importance of B- and C-ring substituents is not understood. Fifteen derivatives of pulchrol with different substituents

  被忽视的热带病影响热带国家的大多数贫困人口。其中包括恰加斯病和利什曼病，主要存在于南美洲和中美洲、非洲和东亚。目前的治疗时间长且具有严重的副作用，因此迫切需要开发替代方案。在这项研究中，我们的研究基于植物代谢物 pulchrol，这是一种天然苯并色烯，已被证明对锥虫和利什曼原虫具有抗寄生虫活性。在最近的一项研究中，我们研究了苯甲醇功能的变化如何影响抗寄生虫活性，但 B 环和 C 环取代基的重要性尚不清楚。pulchrol 的 15 种衍生物，在 1、2、3 和 6 位具有不同的取代基，同时保持 A 环完整，因此，通过全合成制备、测定并与 pulchrol 和阳性对照进行比较。生成的系列和亲本分子在体外测试了对克氏锥虫、巴西利什曼原虫和亚马逊乳杆菌的抗寄生虫活性，以及​​使用 RAW 细胞的细胞毒性。观察到合成的化合物活性存在显着差异，其中一些化合物比阳性对照苯并硝唑对克氏锥虫更有效。一般的趋势是烷基取代基提高效力，尤其是当位于
• [EN] CETP INHIBITORS<br/>[FR] INHIBITEURS DE CETP
  申请人：MERCK & CO INC

  公开号：WO2005100298A1

  公开（公告）日：2005-10-27

  Compounds of Formula (I), including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compounds of Formula 1, A1 and A2 are each an aromatic ring, a 5-6-membered heterocyclic ring, an aromatic ring fused to a heterocyclic ring, a phenyl ring fused to a heterocyclic ring, or a cycloalkyl ring.

  公式（I）的化合物，包括这些化合物的药用可接受盐，是CETP抑制剂，可用于提高HDL-胆固醇，降低LDL-胆固醇，并用于治疗或预防动脉粥样硬化。在公式1的化合物中，A1和A2分别是芳香环，5-6成员杂环，芳香环与杂环融合，苯环与杂环融合或环烷基环。
• [EN] MELANIN-CONCENTRATING HORMONE RECEPTOR ANTAGONISTS AND COMPOSITIONS AND METHODS RELATED THERETO<br/>[FR] ANTAGONISTES DU RECEPTEUR DE L'HORMONE CONCENTRANT LA MELANINE ET COMPOSITIONS ET METHODES CORRESPONDANTES
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2004081005A1

  公开（公告）日：2004-09-23

  Melanin-concentrating hormone (MCH) receptor antagonists are disclosed having utility for the treatment of MCH receptor-based disorders such as obesity. The compounds of this invention have the following structure: including stereoisomers, prodrugs, and pharmaceutically acceptable salts thereof, wherein m, n, X, R1, R2, R3, R4, and R5 are as defined herein. Also disclosed are compositions containing a compound of this invention, as well as methods relating to the use thereof.

  黑色素浓缩激素（MCH）受体拮抗剂被披露具有用于治疗基于MCH受体的疾病，如肥胖症。本发明的化合物具有以下结构：包括立体异构体、前药和其药用盐，其中m、n、X、R1、R2、R3、R4和R5如本文所定义。还披露了含有本发明化合物的组合物，以及与其使用相关的方法。
• Diacylglycerol acyltransferase inhibitors
  申请人：Michoud Christophe

  公开号：US20060258740A1

  公开（公告）日：2006-11-16

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.

  本文提供了以下式(I)的化合物： 以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗诸如肥胖、2型糖尿病和代谢综合征等疾病是有用的。