3-(叔丁基二甲基甲硅烷基氧基)1-丁炔硼酸频那醇酯 | 849820-20-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 3-(叔丁基二甲基甲硅烷基氧基)1-丁炔硼酸频那醇酯
• 中文别名: 3-（叔丁基二甲基甲硅烷氧基）丁-1-炔基硼酸，频哪醇酯
• 英文名称: tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-yn-2-yloxy)silane
• 英文别名: tert-Butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-yn-2-yl)oxy)silane；tert-butyl-dimethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-yn-2-yloxy]silane
• CAS: 849820-20-8
• 化学式: C₁₆H₃₁BO₃Si
• 分子量: 310.317
• InChiKey: KGDJKWYVGUGRCG-UHFFFAOYSA-N

物化性质

• 密度：
  0.9158 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(t-Butyldimethylsilyloxy)but-1-ynylboronic acid, pinacol ester
Synonyms: 2-((3-tert-Butyldimethylsilyloxy)-1-butyn-1-yl)-4,4,5,5-tetramethyl-(1,3,2)dioxaborolane

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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: 3-(t-Butyldimethylsilyloxy)but-1-ynylboronic acid, pinacol ester
CAS number: 849820-20-8

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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, 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: C16H31BO3Si
Molecular weight: 310.3

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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, 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

制备方法与用途

炔基硼酸酯可以参与多种区域选择性和立体选择性的碳-碳键形成过程，包括烯炔的交叉复分解反应和Alder烯反应。1,2

反应信息

• 作为反应物：
  描述：

  3-(叔丁基二甲基甲硅烷基氧基)1-丁炔硼酸频那醇酯 、 5-已烯-2-酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(E)-8-(tert-Butyl-dimethyl-silanyloxy)-7-methylene-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-non-5-en-2-one
  参考文献：
  名称：

  Boron-Directed Regio- and Stereoselective Enyne Cross Metathesis:  Efficient Synthesis of Vinyl Boronate Containing 1,3-Dienes

  摘要：

  Regio- and stereoselective enyne cross metathesis reactions between borylated alkynes and terminal alkenes were realized to provide a variety of functionalized vinyl boronates. High chemical yield and regioselectivity was achieved irrespective of substituents on the alkyne and alkene counterparts, whereas Z/E-selectivity was found to be dependent upon the substituents both on the alkyne and alkene.

  DOI：

  10.1021/ol050542r
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 生成 3-(叔丁基二甲基甲硅烷基氧基)1-丁炔硼酸频那醇酯
  参考文献：
  名称：

  Boron-Directed Regio- and Stereoselective Enyne Cross Metathesis:  Efficient Synthesis of Vinyl Boronate Containing 1,3-Dienes

  摘要：

  Regio- and stereoselective enyne cross metathesis reactions between borylated alkynes and terminal alkenes were realized to provide a variety of functionalized vinyl boronates. High chemical yield and regioselectivity was achieved irrespective of substituents on the alkyne and alkene counterparts, whereas Z/E-selectivity was found to be dependent upon the substituents both on the alkyne and alkene.

  DOI：

  10.1021/ol050542r

文献信息

• [EN] SULFONYLPIPERAZINE DERIVATIVES THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN FOR THE TREATMENT OF DIABETES<br/>[FR] DÉRIVÉS DE SULFONYLPIPÉRAZINE QUI INTERAGISSENT AVEC LA PROTÉINE RÉGULATRICE DE LA GLUCOKINASE POUR LE TRAITEMENT DU DIABÈTE
  申请人：AMGEN INC

  公开号：WO2012027261A1

  公开（公告）日：2012-03-01

  The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

  本发明涉及与葡萄糖激酶调节蛋白相互作用的化合物I式，或其药用盐，此外，本发明涉及使用这些化合物或其药用盐治疗2型糖尿病和其他涉及葡萄糖激酶调节蛋白的疾病和/或症状的方法，以及含有这些化合物或其药用盐的药物组合物。
• Synthesis of β,β-Disubstituted Vinyl Boronates via the Ruthenium-Catalyzed Alder Ene Reaction of Borylated Alkynes and Alkenes
  作者：Eric C. Hansen、Daesung Lee

  DOI：10.1021/ja0424629

  日期：2005.3.1

  Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding β,β-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the ene subunit across the alkyne, which is the opposite stereochemical outcome observed for other internal alkynes

  硼化炔烃和末端烯烃之间的钌催化阿尔德烯反应产生相应的 β,β-二取代乙烯基硼酸酯，对支化异构体具有高选择性。乙烯基硼酸酯部分的立体化学是烯亚基在炔烃上正式反式加成的结果，这与其他内部炔烃观察到的立体化学结果相反。
• COMPOUNDS THAT INTERACT WITH GLUCOKINASE REGULATORY PROTEIN FOR THE TREATMENT OF DIABETES
  申请人：Ashton Kate

  公开号：US20120225854A1

  公开（公告）日：2012-09-06

  The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

  本发明涉及公式I的化合物或其药学上可接受的盐，其与葡萄糖激酶调节蛋白相互作用。此外，本发明涉及使用这些化合物或其药学上可接受的盐以及含有这些化合物或其药学上可接受的盐的药物组合物治疗2型糖尿病以及其他与葡萄糖激酶调节蛋白有关的疾病和/或病况的方法。
• Compounds that interact with glucokinase regulatory protein for the treatment of diabetes
  申请人：Ashton Kate

  公开号：US08431563B2

  公开（公告）日：2013-04-30

  The present invention relates to compounds of Formula I, or pharmaceutically acceptable salts thereof, that interact with glucokinase regulatory protein. In addition, the present invention relates to methods of treating type 2 diabetes, and other diseases and/or conditions where glucokinase regulatory protein is involved using the compounds, or pharmaceutically acceptable salts thereof, and pharmaceutical compositions that contain the compounds, or pharmaceutically acceptable salts thereof.

  本发明涉及式I的化合物或其药学上可接受的盐，该化合物与葡萄糖激酶调节蛋白相互作用。此外，本发明涉及使用该化合物或其药学上可接受的盐以及含有该化合物或其药学上可接受的盐的制药组合物治疗2型糖尿病和其他涉及葡萄糖激酶调节蛋白的疾病和/或病状的方法。