3-丁烯基硼酸 | 379669-72-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 无环羧酸
• 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-丁烯基硼酸
• 中文别名: 丁-3-烯硼酸
• 英文名称: but-3-en-1-ylboronic acid
• 英文别名: But-1-ene-4-boronic acid；but-3-enylboronic acid
• CAS: 379669-72-4
• 化学式: C₄H₉BO₂
• 分子量: 99.9253
• InChiKey: WHTULVNQGYJCSG-UHFFFAOYSA-N

物化性质

• 熔点：
  84-90 °C
• 沸点：
  196.7±33.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,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: But-1-ene-4-boronic acid
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-1-ene-4-boronic acid
CAS number: 379669-72-4

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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: C4H9BO2
Molecular weight: 99.9

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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-丁烯基硼酸 在 potassium hydrogen bifluoride 作用下， 以 乙醚 为溶剂， 以71%的产率得到potassium 1-propenyltrifluoroborate
  参考文献：
  名称：

  扩展有机硼化学：有机三氟硼酸钾的环氧化

  摘要：

  大多数有机硼试剂很容易被各种氧化剂氧化。在这些过程中，有价值的碳-硼键被裂解。在此贡献中检查的有机三氟硼酸盐似乎对许多常见的氧化剂具有抗性。因此，硫醚取代的烷基三氟硼酸盐可以被氧化成相应的砜，同时保留三氟硼酸盐部分。1-三氟硼代烯烃被二环氧乙烷氧化，提供空气稳定的结晶环氧乙烷基三氟硼酸盐。这些有趣的材料在结构上类似于环氧乙烷阴离子，不稳定的中间体，否则将具有巨大的合成效用。最后，首次完成了环氧三氟硼酸盐的 Suzuki-Miyaura 偶联。所描述的化学开始在重要的新方向上扩展有机硼化学。

  DOI：

  10.1021/ja0351140
• 作为产物：
  描述：

  3-Butenylmagnesium bromide 在 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以2 g的产率得到3-丁烯基硼酸
  参考文献：
  名称：

  扩展有机硼化学：有机三氟硼酸钾的环氧化

  摘要：

  大多数有机硼试剂很容易被各种氧化剂氧化。在这些过程中，有价值的碳-硼键被裂解。在此贡献中检查的有机三氟硼酸盐似乎对许多常见的氧化剂具有抗性。因此，硫醚取代的烷基三氟硼酸盐可以被氧化成相应的砜，同时保留三氟硼酸盐部分。1-三氟硼代烯烃被二环氧乙烷氧化，提供空气稳定的结晶环氧乙烷基三氟硼酸盐。这些有趣的材料在结构上类似于环氧乙烷阴离子，不稳定的中间体，否则将具有巨大的合成效用。最后，首次完成了环氧三氟硼酸盐的 Suzuki-Miyaura 偶联。所描述的化学开始在重要的新方向上扩展有机硼化学。

  DOI：

  10.1021/ja0351140

文献信息

• Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids
  作者：Samuel N. Gockel、SangHyun Lee、Brittany L. Gay、Kami L. Hull

  DOI：10.1021/acscatal.1c00105

  日期：2021.5.7

  The three-component carboamination of alkenes is of significant interest due to the ease by which functionalized amines can be produced from readily available chemical building blocks. Previously, a variety of carbon-centered radical precursors have been studied as the carbon components for this reaction; however, the use of general alkyl sources has remained as an unsolved challenge. Herein we present

  烯烃的三组分碳胺化引起了人们的极大兴趣，因为可以很容易地从容易获得的化学结构单元生产官能化胺。此前，已经研究了多种以碳为中心的自由基前体作为该反应的碳组分；然而，一般烷基源的使用仍然是一个未解决的挑战。在此，我们介绍了我们开发一种氧化碳胺化方案的努力，该方案利用烷基硼酸作为以碳为中心的自由基前体。所展示的工作展示了 34 个例子，产率从 17% 到 88% 不等，范围广泛，涉及乙烯基芳烃、胺和烷基硼酸。初步的机理研究表明，烷基硼酸的单电子氧化会产生以碳为中心的自由基中间体，该中间体加成到烯烃上，然后通过铜介导的内球或碳正离子介导的途径形成C-N键。
• [EN] ARYL, HETEROARY, AND HETEROCYCLIC PHARMACEUTICAL COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES ARYLE, HÉTÉROARYLES ET HÉTÉROCYCLIQUES POUR LE TRAITEMENT DE TROUBLES MÉDICAUX
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2018160889A1

  公开（公告）日：2018-09-07

  Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, Formula IV, and Formula V, or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

  提供了抑制补体因子D的抑制剂、药物组合物及其用途，以及它们的制备方法。所提供的化合物包括公式I、公式II、公式III、公式IV和公式V，或其药学上可接受的盐、前药、同位素类似物、N-氧化物或其分离异构体，可选地在药学上可接受的组合物中。本文描述的抑制剂针对因子D并抑制或调节补体级联反应。
• Rapid Access to Highly Functionalized Alkyl Boronates by NiH‐Catalyzed Remote Hydroarylation of Boron‐Containing Alkenes
  作者：Yao Zhang、Bo Han、Shaolin Zhu

  DOI：10.1002/anie.201907185

  日期：2019.9.23

  selective functionalization of relatively simple and readily accessible precursors to produce highly functionalized alkyl boronates is a synthetically useful process. Herein we report a NiH-catalyzed remote hydroarylation process that can, through a synergistic combination of chain walking and subsequent cross-coupling, introduce an aryl group at the adjacent carbon atom of alkyl boronates under mild

  相对简单且容易获得的前体的直接和选择性官能化以产生高度官能化的硼酸烷基酯是合成上有用的方法。本文中，我们报道了NiH催化的远程氢芳构化过程，该过程可以通过链走和随后的交叉偶联的协同组合，在温和的条件下在烷基硼酸酯的相邻碳原子上引入芳基。通过具有中等对映选择性的初步实验，表明还可以实现不对称形式。
• Selecting Double Bond Positions with a Single Cation-Responsive Iridium Olefin Isomerization Catalyst
  作者：Andrew M. Camp、Matthew R. Kita、P. Thomas Blackburn、Henry M. Dodge、Chun-Hsing Chen、Alexander J. M. Miller

  DOI：10.1021/jacs.0c11601

  日期：2021.2.24

  stereoselectivity. The same catalyst, in the presence of Na+, mediates two positional isomerizations to produce 3-alkenes. The synthesis of new iridium pincer-crown ether catalysts based on an aza-18-crown-6 ether proved instrumental in achieving cation-controlled selectivity. Experimental and computational studies guided the development of a mechanistic model that explains the observed selectivity for various functionalized

  双键的催化转位有望成为烯烃作为香料，日用化学品和药物的理想途径。然而，选择性获得特定异构体是一个挑战，通常需要针对不同产品独立开发不同的催化剂。在这项工作中，单一的阳离子响应性铱催化剂选择性地产生两种不同的内部烯烃异构体。在不存在盐的情况下，1-丁烯衍生物的单一位置异构化提供具有优异的区域选择性和立体选择性的2-烯烃。Na +存在下相同的催化剂介导两个位置异构化以生成3-烯烃。事实证明，基于aza-18-crown-6醚的铱铱-crown-crown醚催化剂的合成有助于实现阳离子控制的选择性。实验和计算研究指导了机理模型的开发，该机理模型解释了所观察到的对各种官能化的1-丁烯的选择性，从而为基于非共价修饰的催化剂开发策略提供了见识。
• Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki–Miyaura Couplings
  作者：Zhen-Yu Wang、Biao Ma、Hui Xu、Xing Wang、Xu Zhang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c03048

  日期：2021.11.5

  Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki–Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C–C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

  在此，我们报告了通过钯催化的 Suzuki-Miyaura 交叉偶联反应对芳基酮进行的芳基化、烷基化和烯基化。吡啶-恶唑啉配体的使用是断裂无应变 C-C 键的关键。源自药物和天然产物的芳基酮的后期芳基化证明了该协议的合成效用。