2-(N,N-二甲基氨基甲基)苯硼酸频那醇酯 | 129636-11-9

• 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: 2-(N,N-二甲基氨基甲基)苯硼酸频那醇酯
• 中文别名: 2-（N，N-二甲基氨基甲基）苯基硼酸，频哪醇酯
• 英文名称: N,N-dimethyl-1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine
• 英文别名: N,N-dimethyl-1-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine
• CAS: 129636-11-9
• 化学式: C₁₅H₂₄BNO₂
• 分子量: 261.172
• InChiKey: FYNFIFQXALVLHC-UHFFFAOYSA-N

物化性质

• 沸点：
  340.5±25.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放在惰性气体中，温度控制在2至8℃。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester
Synonyms: N,N-Dimethyl-1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

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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: 2-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester
CAS number: 129636-11-9

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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: C15H24BNO2
Molecular weight: 261.2

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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.

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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：

  2-(N,N-二甲基氨基甲基)苯硼酸频那醇酯 在 oxone 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以69%的产率得到2-二甲胺基甲基苯酚
  参考文献：
  名称：

  通过原位生成铑 (II) ATE 配合物对芳烃进行光诱导邻位 C-H 硼化

  摘要：

  半夹心金属配合物的光诱导原位“氧化”为“高价”阳离子金属配合物已被用于加速催化反应。在这里，我们报告了前所未有的光诱导原位“还原”半夹心金属 [Rh(III)] 配合物到“低价”阴离子金属 [Rh(II)] 配合物，这促进了与缺电子元素的配体交换（二硼）。该策略是通过使用我们开发的官能化环戊二烯基 (Cp A3 ) Rh(III) 催化剂实现的，该催化剂能够实现芳烃的碱性基团导向的室温邻位-C-H 硼化。

  DOI：

  10.1021/jacs.1c05859
• 作为产物：
  描述：

  N,N-二甲基苄胺 、 联硼酸频那醇酯 在 2-氨甲基吡啶 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 甲基环己烷 为溶剂， 反应 16.0h， 以73%的产率得到2-(N,N-二甲基氨基甲基)苯硼酸频那醇酯
  参考文献：
  名称：

  铱催化的甲胺的底物导向的CH硼氢化反应

  摘要：

  已开发出铱催化的苄胺的芳烃CH硼氢化反应，可转化典型的空间控制产物分布，从而提供邻位取代的硼酸酯。发现吡啶甲基胺是取代4,4'-二叔丁基联吡啶的理想配体，以诱导导向作用。初步实验与涉及半不稳定二胺配体的一种胺解离的机理是一致的。

  DOI：

  10.1021/ol301635x

文献信息

• [EN] SOS1 INHIBITORS<br/>[FR] INHIBITEURS DE SOS1
  申请人：MIRATI THERAPEUTICS INC

  公开号：WO2021127429A1

  公开（公告）日：2021-06-24

  The present invention relates to compounds that inhibit Son of sevenless homolog 1 (SOS1) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.

  本发明涉及抑制七无子同源物1（SOS1）活性的化合物。具体而言，本发明涉及化合物、药物组合物和使用方法，例如使用本发明的化合物和药物组合物治疗癌症的方法。
• Remarkably Efficient Iridium Catalysts for Directed C(sp²)–H and C(sp³)–H Borylation of Diverse Classes of Substrates
  作者：Md Emdadul Hoque、Mirja Md Mahamudul Hassan、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.0c13415

  日期：2021.4.7

  aliphatic substrates for selective C(sp3)–H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C–H bonds. A number of late-stage C–H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)–H and C(sp3)–H borylations enabling the method more general

  在这里，我们描述了一类新的 C-H 硼化催化剂的发现及其在芳族、杂芳族和脂肪族系统的区域选择性 C-H 硼化中的应用。新催化剂具有 Ir-C(噻吩基) 或 Ir-C(呋喃基) 阴离子配体，而不是标准 C-H 硼化条件中使用的二胺型中性螯合配体。据报道，这些新发现的催化剂的使用对不同种类的芳烃底物显示出优异的反应性和邻位选择性，并具有高分离产率。此外，该催化剂被证明对大量脂肪族底物的选择性 C(sp 3)–H 键硼化。杂环分子利用 C-H 键固有的高反应性选择性地硼化。已经使用相同的催化剂描述了许多后期 C-H 功能化。此外，我们表明其中一种催化剂甚至可以在露天用于 C(sp 2 )-H 和 C(sp 3 )-H 硼酸化，从而使该方法更加通用。初步的机理研究表明，活性催化中间体是 Ir(bis)boryl 络合物，连接的配体作为双齿配体。总的来说，这项研究强调了新型 C-H 硼酸化催化剂的发现，这些催化剂应该在
• Selective Formation of <i>ortho</i>-Aminobenzylamines by the Copper-Catalyzed Amination of Benzylamine Boronate Esters
  作者：Kathryn A. McGarry、Alexi A. Duenas、Timothy B. Clark

  DOI：10.1021/acs.joc.5b01074

  日期：2015.7.17

  The copper-catalyzed coupling between benzylamino boronate esters and aryl amines has been investigated. Formation of ortho-aminobenzylamines was achieved under oxidative conditions in the presence of copper(II) acetate. The major side product of the transformation is the homocoupling of the aryl boronate ester. The formation of the desired diamines was found to be improved in the absence of base,

  已经研究了苄基氨基硼酸酯和芳基胺之间的铜催化偶联。邻位形成在乙酸铜（II）的存在下，在氧化条件下获得-氨基苄胺。转化的主要副产物是芳基硼酸酯的均偶联。发现在不存在碱的情况下所需二胺的形成得到改善，相对于均偶联产物增加了选择性。在反应条件下，在硼酸酯底物和苯胺偶联配偶体上都可以同时接受给电子和吸电子取代基。相邻苄胺基团的存在似乎增强了硼酸酯的反应性并影响了最终产物的分布，这可能是通过影响催化循环中金属转移的竞争速率来实现的。
• Synthesis of Biaryl Ethers by the Copper-Catalyzed Chan–Evans–Lam Etherification from Benzylic Amine Boronate Esters
  作者：Justin S. Marcum、Kathryn A. McGarry、Carl J. Ferber、Timothy B. Clark

  DOI：10.1021/acs.joc.6b01254

  日期：2016.9.2

  benzylic amines with phenols has been achieved to provide biaryl ethers that are prevalent in biologically active compounds. A variety of substitution patterns on the aryl boronate ester and the phenol are tolerated under the reaction conditions, providing moderate to high yields. A competition reaction between phenol and aniline revealed condition-dependent selectivity in which the phenol could be highly

  已经实现了邻苯甲酰化苄基胺与苯酚的铜催化醚化，以提供在生物活性化合物中普遍存在的联芳醚。在反应条件下，可以耐受芳基硼酸酯和苯酚上的多种取代方式，从而提供中等至高收率。苯酚和苯胺之间的竞争反应显示了条件依赖性的选择性，其中苯酚可能比苯胺更受青睐。
• Synthesis and Structure–Activity Relationships of 5′-Aryl-14-alkoxypyridomorphinans: Identification of a μ Opioid Receptor Agonist/δ Opioid Receptor Antagonist Ligand with Systemic Antinociceptive Activity and Diminished Opioid Side Effects
  作者：Rakesh H. Vekariya、Wei Lei、Abhisek Ray、Surendra K. Saini、Sixue Zhang、Gabriella Molnar、Deborah Barlow、Kelly L. Karlage、Edward J. Bilsky、Karen L. Houseknecht、Tally M. Largent-Milnes、John M. Streicher、Subramaniam Ananthan

  DOI：10.1021/acs.jmedchem.0c00503

  日期：2020.7.23

  14-position of the morphinan as a mixed μ opioid receptor (MOR) agonist and δ/κ opioid receptor (DOR/KOR) antagonist with potent antinociceptive activity and diminished tolerance and dependence in rodents. Structural variations at the 5′- and 14-positions of this molecule gave insights into the structure–activity relationships for binding and functional activity. Subtle structural changes exerted significant

  我们之前鉴定了一种吡啶吗啡喃 ( 6 , SRI-22138)，在吡啶的 5'-位具有 4-氯苯基取代基，在吗啡喃的 14-位具有 3-苯基丙氧基作为混合 μ 阿片受体 (MOR) 激动剂和 δ/κ 阿片受体 (DOR/KOR) 拮抗剂，具有强效镇痛活性并降低啮齿动物的耐受性和依赖性。该分子 5' 和 14 位的结构变化让我们深入了解了结合和功能活性的结构-活性关系。细微的结构变化产生了重大影响，特别是对化合物在 MOR 中作为激动剂发挥作用的能力。体内评估鉴定出化合物20(SRI-39067) 作为 MOR 激动剂/DOR 拮抗剂，在小鼠甩尾试验中产生全身活性强效镇痛活性，与吗啡相比，耐受性、依赖性/戒断、奖赏责任和呼吸抑制降低。这些结果支持混合 MOR 激动剂/DOR 拮抗剂配体可能作为新型阿片类镇痛剂出现并减少副作用的假设。