3-甲氧基-4-甲苯硼酸 | 917757-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基-4-甲苯硼酸
• 中文别名: 3-甲氧基-4-甲基苯硼酸；(3-甲氧基-4-甲基)苯硼酸；3-甲氧基-4-甲苯硼酸,97%
• 英文名称: 3-methoxy-4-methylphenylboronic acid
• 英文别名: (3-methoxy-4-methylphenyl)boronic acid
• CAS: 917757-15-4
• 化学式: C₈H₁₁BO₃
• mdl: MFCD08274479
• 分子量: 165.985
• InChiKey: UMGAGEBOUIODFE-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194°C
• 沸点：
  318.3±52.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-Methoxy-4-methylphenylboronic 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.
3-Methoxy-4-methylphenylboronic acid
Ingredient name:
CAS number: 917757-15-4

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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.
Storage: Store in closed vessels.

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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: C8H11BO3
Molecular weight: 166.0

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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：

  3-甲氧基-4-甲苯硼酸 在 四氮唑 、 叔丁基过氧化氢 、 四(三苯基膦)钯 、 三溴化硼 、 碳酸氢钠 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 22.25h， 生成 (R_p)-4,12-di(4-methyl-phenyl-3-yl)-[2.2]paracyclophane-hydrogenphosphate
  参考文献：
  名称：

  平面手性磷酸与[2.2]对环苯甲酰基骨架作为有机催化剂的高对映选择性氮杂-弗里德尔-工艺反应的设计

  摘要：

  合成了一种新型的带有[2.2]对环环烷骨架的新型强力平面手性磷酸，它被证明是不对称氮杂-Friedel-Crafts反应的最佳催化剂，可用于首次以良好的收率和良好的对映选择性合成富含对映体的苯乙烯基吲哚基甲胺衍生物（93 –> 99％ee），催化剂负载量为0.5–1 mol％。

  DOI：

  10.1021/acs.orglett.9b01127
• 作为产物：
  描述：

  硼酸三异丙酯 、 2-甲基-5-溴苯甲醚 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.75h， 以97%的产率得到3-甲氧基-4-甲苯硼酸
  参考文献：
  名称：

  轻松合成含1,2-二酮的山茱tan类似物以生成人羧酸酯酶抑制剂

  摘要：

  最近，基于丹参酮已经鉴定出一系列选择性的人羧酸酯酶抑制剂，其具有1，2-二酮基团的生物活性分子作为萘醌核心的一部分。不幸的是，这类化合物的合成很复杂。在这里，我们描述了一种使用统一方法生成含1,2-二酮的二萜类化合物的新方法，该方法将硼酸通过Suzuki偶联与乙烯基溴-环己烯衍生物连接，然后进行电环化并氧化成邻位-菲醌。这允许构建一组含有一系列取代基（甲基，异丙基，氟，甲氧基）的米替隆类似物，这些取代基已用于与两种人羧酸酯酶同工型发展初步的SAR。因此，我们已经合成这些酶（K的高度有效的抑制剂我 <15纳米），其保持所述芯丹参酮支架。因此，我们开发了一种简便易行且可重现的方法，用于合成abetanene类似物，从而产生了一系列米替农衍生物，这些衍生物将是评估羧酸酯酶生物学的有用工具化合物。

  DOI：

  10.1016/j.ejmech.2018.02.052

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS D'UTILISATION
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2015058084A1

  公开（公告）日：2015-04-23

  The present application discloses compounds that are inhibitors of Btk, compounds that are inhibitors of ΡΒΚδ, and compounds that are dual inhibitors of both Btk and PI3Kδ. Also described are methods for synthesizing such inhibitors and methods for using such inhibitors for the treatment of diseases wherein inhibition of Btk and PI3Kδ provides a therapeutic benefit to a patient having the disease.

  本申请公开了抑制Btk的化合物、抑制ΡΒΚδ的化合物，以及既是Btk又是PI3Kδ的双重抑制剂的化合物。还描述了合成这些抑制剂的方法，以及利用这些抑制剂治疗疾病的方法，其中抑制Btk和PI3Kδ对患有该疾病的患者提供治疗益处。
• Bicyclic sulfonamide compounds as sodium channel inhibitors
  申请人：AMGEN INC.

  公开号：US09212182B2

  公开（公告）日：2015-12-15

  The present invention provides compounds of Formula I, and pharmaceutically acceptable salts thereof, that are inhibitors of voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders and itch. Also provided are pharmaceutical compositions containing compounds of the present invention.

  本发明提供了式I的化合物及其药学上可接受的盐，这些化合物是钠通道的抑制剂，特别是Nav1.7。这些化合物对于治疗与钠通道活性相关的疾病，如疼痛障碍和瘙痒，是有用的。还提供了含有本发明化合物的药物组合物。
• Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols
  作者：Eric D. Nacsa、David W. C. MacMillan

  DOI：10.1021/jacs.7b12768

  日期：2018.3.7

  two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide

  大自然通常使用醇作为离去基团，因为 DNA 生物合成依赖于通过自由基介导的“自旋中心转移”（SCS）机制从核糖核苷二磷酸中去除水。然而，由于醇在双电子途径中的低反应性，醇在合成化学中作为烷化剂仍然没有得到充分利用。我们在此报告了基于自旋中心位移的机械原理，使用醇作为烷化剂的醛的对映选择性 α-苄基化。该策略利用光氧化还原和有机催化的双重激活模式，通过 SCS 与醇结合，并用催化生成的烯胺捕获产生的苄基自由基。机理研究为 SCS 作为关键的基本步骤提供了证据，确定了竞争反应的起源，
• 双环酮磺酰胺化合物
  申请人：美国安进公司

  公开号：CN107531705B

  公开（公告）日：2020-09-18

  本发明提供式(I)化合物，其中：式(II)为如本说明书中所定义的，其中：其对映异构体、非对映异构体、阻转异构体或其混合物或其药学上可接受的盐，这些化合物是电压门控钠通道、具体地为Nav 1.7的抑制剂。所述化合物适用于治疗可通过抑制钠通道治疗的疾病，例如疼痛病症、咳嗽或瘙痒症。本文还提供含有本发明化合物的药物组合物。
• Design, synthesis and biological evaluation of novel vicinal diaryl-substituted 1H-Pyrazole analogues of combretastatin A-4 as highly potent tubulin polymerization inhibitors
  作者：Romeo Romagnoli、Paola Oliva、Maria Kimatrai Salvador、Maria Encarnacion Camacho、Chiara Padroni、Andrea Brancale、Salvatore Ferla、Ernest Hamel、Roberto Ronca、Elisabetta Grillo、Roberta Bortolozzi、Fatlum Rruga、Elena Mariotto、Giampietro Viola

  DOI：10.1016/j.ejmech.2019.111577

  日期：2019.11

  derivatives, prepared as cis-rigidified combretastatin A-4 (CA-4) analogues, were synthesized and evaluated for their in vitro antiproliferative against six different cancer cell lines and, for selected highly active compounds, inhibitory effects on tubulin polymerization, cell cycle effects and in vivo potency. We retained the 3′,4′,5′-trimethoxyphenyl moiety as ring A throughout the present investigation

  一系列3-（3'，4'，5'-三甲氧基苯基）-4-取代的1 H-吡唑及其相关的3-芳基-4-（3'，4'，5'-三甲氧基苯基）-1- H合成了作为顺式刚性康普他汀A-4（CA-4）类似物制备的对吡唑区域异构衍生物，并评估了其对六种不同癌细胞系的体外抗增殖作用，并针对某些高活性化合物对微管蛋白聚合的抑制作用进行了评估，细胞周期效应和体内效力。在整个本研究中，我们保留了3'，4'，5'-三甲氧基苯基部分作为环A，并通过添加吸电子（OCF 3，CF 3）或第二个芳基环上的电子释放基团（烷基和烷氧基），对应于CA-4的B环，位于吡唑核的3或4位。另外，B环被苯并[ b ]噻吩-2-基部分取代。对于许多化合物，它们的活性均大于或与CA-4相当。在两种区域异构衍生物中观察到最大活性，其特征在于在1 H的C-3和C-4位置存在4-乙氧基苯基和3'，4'，5'-三甲氧基苯基，反之亦然-吡唑环。数据表明，3