1-甲基吲哚-5-硼酸频哪醇酯 | 837392-62-8

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基吲哚-5-硼酸频哪醇酯
• 中文别名: N-甲基吲唑-5-硼酸；1-甲基吲哚-5-硼酸嚬哪醇酯；1-甲基吲哚-5-硼酸频那醇酯
• 英文名称: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• 英文别名: 1-methylindole-5-boronic acid pinacol ester；1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
• CAS: 837392-62-8
• 化学式: C₁₅H₂₀BNO₂
• 分子量: 257.14
• InChiKey: JQLYKUPEQYNDFF-UHFFFAOYSA-N

物化性质

• 熔点：
  110-114 °C (lit.)
• 沸点：
  391.3±15.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methylindole-5-boronic acid, pinacol ester
Synonyms: 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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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-Methylindole-5-boronic acid, pinacol ester
CAS number: 837392-62-8

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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: C15H20BNO2
Molecular weight: 257.1

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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, 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：

  1-甲基吲哚-5-硼酸频哪醇酯 在 盐酸 作用下， 反应 6.0h， 以87.3%的产率得到1-甲基吲哚-5-硼酸
  参考文献：
  名称：

  一种苯并杂环硼酸的制备方法

  摘要：

  本发明提供了一种苯并杂环硼酸的制备方法，所述制备方法包括以下步骤：(1)将式I所示苯并杂环化合物溶于溶剂A中，得到A溶液，将硼基化试剂溶于溶剂B中，得到B溶液，将钯催化剂和碱性试剂固载在连续流动反应器通道上，将A溶液与B溶液连续加料反应，流出反应管后终止反应得到中间体；(2)将步骤(1)得到的中间体经水解反应后得到所述苯并杂环硼酸；本发明所提供的制备方法，使用流动化学技术合成苯并杂环硼酸，相比于现有技术中的方法，本发明中产物的收率在86％以上，最高可达90％以上，产率非常高，并且反应速率快，大大降低了反应的能耗，并且可操作性高，自动化程度高，有利于生产操作，利于工业化生产。

  公开号：

  CN108440588A
• 作为产物：
  描述：

  5-碘吲哚 在 1,10-菲罗啉 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 反应 30.5h， 生成 1-甲基吲哚-5-硼酸频哪醇酯
  参考文献：
  名称：

  在无过渡金属的碱性条件下竞争性脱卤与芳基碘化物和溴化物的硼化反应

  摘要：

  在这项工作中，描述了可选择性控制的碱促进的无过渡金属的硼化和芳基卤化物的脱卤作用。在硼化条件下，通过仔细控制硼化条件可以很好地控制作为竞争性副反应而出现的脱卤作用。另一方面，使用苯甲醛作为氢源的脱卤也已经完成。芳基卤化物的直接自由基硼化和脱卤的应用证明了它们在面向药物的有机合成中的合成实用性。根据实验证据，揭示了两种竞争反应的t BuOK / 1,10-Phen激发的自由基性质。

  DOI：

  10.1021/acs.joc.9b01350

文献信息

• Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
  作者：Justin S. Marcum、Courtney C. Roberts、Rajith S. Manan、Tia N. Cervarich、Simon J. Meek

  DOI：10.1021/jacs.7b08575

  日期：2017.11.8

  Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

  据报道N-杂芳烃向末端和内部1，3-二烯的催化对映选择性加成。5 mol％的Rh催化剂促进了反应，该催化剂由新型手性钳碳二碳烯配体支撑，该配体可提供高达95％的收率和高达98：2 er的烯丙基取代的芳烃。机械和透视证据呈现支持经由铑（III）-η反应进行3 -烯丙基。
• [EN] ANTICANCER BENZOPYRAZINES VIA THE INHIBITION OF FGFR KINASES<br/>[FR] BENZOPYRAZINES ANTICANCÉREUSES PAR LE BIAIS DE L'INHIBITION DE FGFR KINASES
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013061081A1

  公开（公告）日：2013-05-02

  The invention relates to new quinoxaline derivative compounds, to pharmaceutical compositions comprising said compounds, to processes for the preparation of said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  这项发明涉及新的喹啉衍生物化合物，包括含有该化合物的药物组合物，用于制备该化合物的方法以及该化合物在治疗疾病（例如癌症）中的用途。
• Suzuki–Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
  作者：Shigehiro Asano、Seiji Kamioka、Yoshiaki Isobe

  DOI：10.1016/j.tet.2011.10.057

  日期：2012.1

  Suzuki–Miyaura cross-coupling reaction with 2-heteroarylboronic acids is generally challenging due to these acids easy decomposition. To overcome this problem, we developed a coupling method that uses 2-heteroaryl pinacol boronates in the presence of 1.0 mol % Pd(OAc)2 and 2.0 mol % S-Phos with 4 equiv amount of LiOH in dioxane and H2O at 80 °C for 30 min. This developed method allowed for the synthesis

  由于这些酸易于分解，因此与2-杂芳基硼酸的铃木-宫浦交叉偶联反应通常具有挑战性。为克服此问题，我们开发了一种偶合方法，该方法在1.0 mol％Pd（OAc）2和2.0 mol％S-Phos的存在下，在80％的二恶烷和H 2 O中于80摩尔下使用2-杂芳基频哪醇硼酸酯°C 30分钟。这种发达的方法允许从2-氯嘧啶基衍生物高产率地合成各种各样的2-杂芳基嘧啶，并且还可以用于由杂芳基氯化物制备各种联芳基衍生物。
• Enantioselective Synthesis of Functionalized Arenes by Nickel‐Catalyzed Site‐Selective Hydroarylation of 1,3‐Dienes with Aryl Boronates
  作者：Justin S. Marcum、Tiffany R. Taylor、Simon J. Meek

  DOI：10.1002/anie.202004982

  日期：2020.8.10

  A catalytic method for the site‐selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3‐dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol % of a readily available monodentate phosphoramidite‐Ni complex in ethanol, affording a variety of enantioenriched products in up to 96 % yield and

  报道了一种通过端基和内部1,3-二烯与芳基频哪醇硼酸酯的分子间氢芳基化反应来催化官能化芳烃的选择性和对映选择性合成的催化方法。5.0 mol％的乙醇中容易获得的单齿亚磷酰胺-Ni络合物可促进反应，从而以高达96％的收率和99：1 er提供多种对映体富集的产品。机理研究表明，Ni-烯丙基的形成是不可逆的，并且与芳基硼酸酯的性质有关。
• [EN] SUBSTITUTED INDOLE MCL-1 INHIBITORS<br/>[FR] INHIBITEURS D'INDOLES MCL-1 SUBSTITUÉS
  申请人：UNIV VANDERBILT

  公开号：WO2017152076A1

  公开（公告）日：2017-09-08

  The present disclosure provides for compounds that inhibit the activity of an anti- apoptotic Bcl-2 family member Myeloid cell leukemia-1 (Mcl-1) protein. The present disclosure also provides for pharmaceutical compositions as well as methods for using compounds for treatment of diseases and conditions (e.g., cancer) characterized by the over- expression or dysregulation of Mcl-1 protein.

  本公开提供了抑制抗凋亡Bcl-2家族成员髓细胞白血病-1（Mcl-1）蛋白活性的化合物。本公开还提供了用于治疗由Mcl-1蛋白过度表达或失调所特征的疾病和病况（例如癌症）的药物组合物以及使用化合物的方法。