(3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷 | 108794-10-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: (3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷
• 英文名称: 4-[(tert-butyldimethylsilyl)oxy]-1-butene
• 英文别名: (but-3-en-1-yloxy)(tert-butyl)dimethylsilane；(but-3-enyloxy)(tert-butyl)dimethylsilane；1-tert-butyldimethylsilyloxy-3-butene；1-(tert-butyldimethylsiloxy)-3-butene；(but-3-en-1-yloxy) (t-butyl)dimethylsilane；but-3-enoxy-tert-butyl-dimethyl-silane；But-3-enyloxy-tert-butyl-dimethyl-silane；but-3-enoxy-tert-butyl-dimethylsilane
• CAS: 108794-10-1
• 化学式: C₁₀H₂₂OSi
• mdl: MFCD09033284
• 分子量: 186.37
• InChiKey: SQEJDOVXJLMAJA-UHFFFAOYSA-N

物化性质

• 沸点：
  180.8±9.0 °C(Predicted)
• 密度：
  0.807±0.06 g/cm3(Predicted)
• 保留指数：
  1030

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (But-3-en-1-yloxy)-tert-butyldimethylsilane
Synonyms:

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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: (But-3-en-1-yloxy)-tert-butyldimethylsilane
CAS number: 108794-10-1

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H22OSi
Molecular weight: 186.4

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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

反应信息

• 作为反应物：
  描述：

  (3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷 在 正丁基锂 、 臭氧 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.75h， 生成 N-[5-(tert-butyldimethylsilanyloxy)pent-2-enoyl]benzamide
  参考文献：
  名称：

  奎宁和奎尼丁的催化不对称全合成

  摘要：

  奎宁和奎尼丁的催化不对称合成分 16 步完成。最近开发的salen（Al）催化的氰基乙酸甲酯的对映选择性迈克尔加成用于将关键的C4立体中心设置为92％ee，并且后期不对称二羟基化用于区分常见中间体并获得两种所需的具有高的非对映体产品选择性。

  DOI：

  10.1021/ja039550y
• 作为产物：
  描述：

  4-(叔丁基二甲基硅杂氧基)-1-丁炔 在 氢气 、 二乙烯三胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以96%的产率得到(3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷
  参考文献：
  名称：

  氮化硼催化剂上钯的研制及其在炔烃半加氢中的应用

  摘要：

  完成了一种新型的载于氮化硼催化剂上的钯（Pd / BN）的制备方法。Pd / BN广泛适用于在二亚乙基三胺（DETA）的存在下对单取代炔烃和双取代炔烃进行半氢化反应，以提供相应的烯烃，这对半氢化反应显示出前所未有的促进作用，而对过氢化反应则显示出抑制作用烷烃。

  DOI：

  10.1002/adsc.201100936
• 作为试剂：
  描述：

  4-碘-1-甲苯磺酰-1H-咪唑 在 四(三苯基膦)钯 (3-丁烯-1-基氧基)(二甲基)(2-甲基-2-丙基)硅烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以55%的产率得到1,1'-Di-p-tosyl-4,4'-biimidazole
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Acetyl-4(5)-(1,2,4-trihydroxybutyl)imidazoles

  摘要：

  A method for preparing trihydroxybutyl analogues of the biologically active compound 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole (THI) is reported. This method employs a palladium(0)catalyzed coupling of 1-(ethoxymethyl)-4-iodoimidazole (3a) to functionalized vinylstannane 11, 1-alkynylstannane 16, or alkyne 10 to introduce the C-4 imidazole 4-carbon side chain, The 1,2-dihydroxyfunctionality of the butyl side chain was introduced by a Sharpless catalytic asymmetric dihydroxylation.

  DOI：

  10.1021/jo00113a016

文献信息

• [EN] GROUP 5 METAL COMPLEXES FOR CATALYTIC AMINE FUNCTIONALIZATION<br/>[FR] COMPLEXES MÉTALLIQUES DU GROUPE 5 POUR LA FONCTIONNALISATION CATALYTIQUE D'AMINE
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2018213938A1

  公开（公告）日：2018-11-29

  This application pertains to group 5 metal complexes having the structure of Formula I; and their potential utility in catalyzing α-alkylation of secondary amine-containing moieties.

  这种应用涉及具有公式I结构的5族金属配合物；以及它们在催化含有次要胺基团的α-烷基化中的潜在用途。
• Site-Selective Mono-Oxidation of 1,2-Bis(boronates)
  作者：Lu Yan、James P. Morken

  DOI：10.1021/acs.orglett.9b01204

  日期：2019.5.17

  Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

  通过在1-丁醇溶剂中使用三甲胺N-氧化物来完成邻位双（硼酸酯）的位点选择性氧化。该反应在一系列底物上以良好的效率和选择性进行，从而提供了2-氢-1-硼酸酯，该酯被证明是手性结构单元合成中的通用中间体。
• One-pot sequential cross-metathesis/hydride reduction: highly stereoselective synthesis of primary (E)-allylic alcohols from terminal olefins
  作者：Tapas Paul、Gopal Sirasani、Rodrigo B. Andrade

  DOI：10.1016/j.tetlet.2008.03.132

  日期：2008.5

  Several di- and trisubstituted primary (E)-allylic alcohols have been prepared from the corresponding terminal olefins in a highly stereoselective manner (>20:1 E/Z) by sequencing olefin cross-metathesis (CM) with hydride reduction (DIBAL-H) in good yields utilizing only commercially available reagents in a one-pot fashion. The method is a reliable alternative to the direct CM of terminal olefins with

  通过以氢化物还原法对烯烃交叉复分解（CM）进行测序（DIBAL-H），从相应的末端烯烃以高度立体选择性的方式（> 20：1 E / Z）制备了几种二和三取代的伯（E）烯丙基醇。）仅使用一锅法仅使用市售试剂即可获得高收率）。该方法是端烯与烯丙醇直接CM的可靠替代方法，后者并不总是立体选择性的，而是高度依赖底物的。
• Catalytic Asymmetric Addition of Alkylzinc and Functionalized Alkylzinc Reagents to Ketones
  作者：Sang-Jin Jeon、Hongmei Li、Celina García、Lynne K. LaRochelle、Patrick J. Walsh

  DOI：10.1021/jo048683e

  日期：2005.1.1

  We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl ethers, alkyl chlorides, and alkyl bromides. In general, the resulting tertiary alcohol products are isolated with high ee's. With some substrates, yields are low as a result

  我们描述了将简单和功能化的二烷基锌试剂催化不对称添加到各种饱和酮和烯酮中的完整报告。官能化的有机锌试剂包含酯，甲硅烷基醚，烷基氯和烷基溴化物。通常，将所得的叔醇产物与高ee分离。对于某些底物，由于醛醇副产物的形成，收率低。大多数基材都经过添加，其良率高达91％。
• Cobalt-Catalyzed Regioselective Olefin Isomerization Under Kinetic Control
  作者：Xufang Liu、Wei Zhang、Yujie Wang、Ze-Xin Zhang、Lei Jiao、Qiang Liu

  DOI：10.1021/jacs.8b01815

  日期：2018.6.6

  Olefin isomerization is a significant transformation in organic synthesis, which provides a convenient synthetic route for internal olefins and remote functionalization processes. The selectivity of an olefin isomerization process is often thermodynamically controlled. Thus, to achieve selectivity under kinetic control is very challenging. Herein, we report a novel cobalt-catalyzed regioselective olefin

  烯烃异构化是有机合成的重大转变，为内烯烃和远程功能化过程提供了一条便捷的合成路线。烯烃异构化过程的选择性通常受热力学控制。因此，在动力学控制下实现选择性是非常具有挑战性的。在此，我们报告了一种新型的钴催化区域选择性烯烃异构化反应。通过利用可微调的 NNP 钳配体结构，该催化系统具有区域选择性的高动力学控制。这种温和的催化系统能够以优异的产率和区域选择性将带有多种官能团的 1,1-二取代烯烃异构化。这种转化的合成效用通过高度选择性地制备用于全合成 minfiensine 的关键中间体得到了强调。此外，还开发了一种新策略，通过在双键的 γ 位上安装取代基来实现 1-烯烃到 2-烯烃的选择性单异构化。机理研究支持原位生成的 Co-H 物种经历了双键/β-H 消除序列的迁移插入以提供异构化产物。由于对β-H消除步骤的区域选择性的有效配体控制，在这种钴催化的烯烃异构化中总是优选受阻较小的烯烃产物。开发了一种新策略，通过在双键的