3-乙酰氧基-1-丙烯基硼酸频哪酯 | 161395-97-7

• 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-乙酰氧基-1-丙烯基硼酸频哪酯
• 英文名称: (E)-3-acetoxy-1-propenylboronic acid pinacol ester
• 英文别名: (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl acetate；3-Acetoxy-1-propenylboronic acid pinacol ester；[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enyl] acetate
• CAS: 161395-97-7
• 化学式: C₁₁H₁₉BO₄
• mdl: MFCD03788751
• 分子量: 226.08
• InChiKey: ZXBRLGZFCXGTBA-VOTSOKGWSA-N

物化性质

• 沸点：
  250.4±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H335,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Acetoxy-1-propenylboronic acid pinacol ester
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: 3-Acetoxy-1-propenylboronic acid pinacol ester
CAS number: 161395-97-7

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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: C11H19BO4
Molecular weight: 226.1

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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.

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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-乙酰氧基-1-丙烯基硼酸频哪酯 在 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 叔丁基锂 、 lithium chloride 作用下， 以 乙醚 、 乙酸乙酯 、 正戊烷 为溶剂， 反应 5.83h， 生成
  参考文献：
  名称：

  双(烯基)硼酸酯的化学选择性和立体选择性烯丙基化

  摘要：

  Ir 催化的双烯基硼酸酯烯丙基化反应具有高基团选择性（取代程度较高的烯烃的迁移）、对映选择性和非对映选择性。所得光学活性叔烯丙基硼试剂可以通过硼的直接取代或通过烯丙基官能化参与转化。形成环状和非环状产物，并创建多达五个新的立体中心。

  DOI：

  10.1002/anie.202407824
• 作为产物：
  描述：

  乙酸炔丙酯 、 频那醇硼烷 在 bis(cyclohexanyl)borane 作用下， 反应 24.0h， 以77%的产率得到3-乙酰氧基-1-丙烯基硼酸频哪酯
  参考文献：
  名称：

  烯基从硼转移到硼制备(E)-1-烯基硼酸频哪醇酯

  摘要：

  研究了 (E)-1-烯基硼酸频哪醇酯 3 的两种合成路线。1-炔烃 I 与 1,3,2-苯并二恶硼烷（儿茶酚硼烷）的硼氢化反应是在 THF 中的 BH 3 与儿茶酚反应生成的，在 THF 中催化量的二环己基硼烷存在下，室温下进行，得到相应的 (E)-1-烯基硼酸儿茶酚酯 2. 用 2,3-二甲基-2,3-丁二醇 (频哪醇) 处理所得酯 2 容易得到所需产物 3，其对空气、水分和色谱不敏感，整体产量好到高。顺序反应是以一锅方式从THF中的BH 3 到3的高效途径。或者，用 4,4,5,5-四甲基-1,3 对 1 进行硼氢化，2-二氧硼烷（频哪醇硼烷）是在催化量的二环己基硼烷的存在下在室温下在纯净条件下获得的，以良好至极好的产率直接提供相应的产物 3。从充分利用频哪醇硼烷和不使用溶剂的角度来看，该路线非常有效且对环境无害，并且能够使用多种炔烃1，包括官能化的炔烃1，例如HCCCH 2 Cl和HCCCH

  DOI：

  10.1055/s-2004-829165

文献信息

• Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (<i>E</i>,<i>E</i>)-1,3-Dienes
  作者：Dattatraya H. Dethe、Nagabhushana C. Beeralingappa、Amar Uike

  DOI：10.1021/acs.joc.0c02823

  日期：2021.2.19

  An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst

  已经开发出活化烯烃和乙烯基硼酸酯衍生物之间的氧化交叉偶联反应，以用于合成有用的（E，E）-1，3-二烯的高度立体选择性的结构。该反应的亮点在于，使用便宜的[RuCl 2（p- Cymene）] 2催化剂，可从无碱，无配体和温和的催化条件下获得独特的立体选择性（仅E，E-异构体）。
• Boron-tethered oxidopyrylium-based [5 + 2] cycloadditions
  作者：Seth I. Corrie、Aaron C. Pearce、Jacob P. Grabowski、Kee A. Randolph、Wentao Guo、Dean J. Tantillo、T. Andrew Mitchell

  DOI：10.1016/j.tetlet.2022.154094

  日期：2022.9

  Oxidopyrylium-based [5 + 2] cycloadditions between diethanolamine appended silyloxypyrones and organoboronic acid derivatives were achieved. Evidence for the diethanolamine boronate (i.e. DABO) complex was observed by 1H NMR at room temperature with boronic acids and [5 + 2] cycloaddition was achieved in a single reaction mixture in DCE. Pinacol boronates required elevated temperature (140 °C) in refluxing p-xylene

  实现了二乙醇胺附加的甲硅烷氧基吡喃酮和有机硼酸衍生物之间的基于氧化吡喃的 [5 + 2] 环加成反应。在室温下用硼酸通过1 H NMR观察到二乙醇胺硼酸盐（即 DABO）络合物的证据，并且在 DCE 中的单一反应混合物中实现了 [5 + 2] 环加成。频哪醇硼酸盐在回流对二甲苯中需要升高温度 (140 °C)，但可以使用硼酸不易获得的产品。理论计算为异步协调过渡状态提供了证据。观察到良好的官能团耐受性，产物分离为氧杂双环[3.2.1]-辛烷 DABO 环加合物。
• Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates
  作者：Krishna Kishore Kukkadapu、Aziz Ouach、Pedro Lozano、Michel Vaultier、Mathieu Pucheault

  DOI：10.1021/ol201661s

  日期：2011.8.5

  Three-carbon highly functionalized gamma-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An Ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%.
• A facile method for the preparation of 4-hydroxy-Δ2-isoxazolines via a cycloaddition/oxidation procedure employing nitrile oxides and vinylboronic esters
  作者：Richard H. Wallace、Jinchu Liu

  DOI：10.1016/s0040-4039(00)78326-2

  日期：1994.10

  The 1,3-dipolar cycloaddition of aromatic nitrile oxides with trans-1,2-disubstituted vinylboronic esters affords the 4-boronic ester substituted Delta(2)-isoxazoline as the major regioisomer. If the reaction mixture is treated with t-BuOOH the corresponding 4-hydroxy-Delta(2)-isoxazolines are obtained in good yield.
• Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids
  作者：Alexey V. Kalinin、Stefan Scherer、Victor Snieckus

  DOI：10.1002/anie.200351312

  日期：2003.7.28