5-己烯yl硼酸 | 1072952-16-9

• 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: 5-己烯yl硼酸
• 中文别名: 5-己烯基硼酸
• 英文名称: hex-5-en-1-ylboronic acid
• 英文别名: 5-hexenylboronic acid；hex-5-enylboronic acid
• CAS: 1072952-16-9
• 化学式: C₆H₁₃BO₂
• mdl: MFCD10567048
• 分子量: 127.979
• InChiKey: JXFKAWIGNACKQN-UHFFFAOYSA-N

物化性质

• 熔点：
  67-73 °C
• 沸点：
  241.5±33.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Hexenylboronic 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: 5-Hexenylboronic acid
CAS number: 1072952-16-9

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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: C6H13BO2
Molecular weight: 128.0

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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：

  5-己烯yl硼酸 在 三乙胺 作用下， 以54 %的产率得到5-己烯-1-醇
  参考文献：
  名称：

  以菠菜为光催化剂的红光诱导有机硼化合物高效好氧氧化

  摘要：

  已经开发了一种简单且通用的红光诱导有机硼化合物氧化以获得羟基，菠菜作为醇中的光催化剂。这种温和的协议显示了广泛的底物范围，并以中等至优异的产量提供了广泛的脂肪醇和酚。值得注意的是，该方法的稳健性适用于 B(OH) 2、Bpin、Bneo 和 BF 3对不同光（包括红色、蓝色和阳光）作出反应的 K 底物。更大规模的实验和绿色化学指标分析证明，这是一种稳健且绿色的方法，甚至可以仅使用厨房设备和配料进行。进一步的机理研究表明，该反应可能涉及由光诱导电子转移过程产生的超氧阴离子自由基。

  DOI：

  10.1039/d2gc03055a
• 作为产物：
  描述：

  2-(hex-5-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 sodium periodate 、 ammonium acetate 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 5-己烯yl硼酸
  参考文献：
  名称：

  对映选择性镍催化迁移加氢芳基化形成手性α-芳基烷基硼酸酯的中继催化策略

  摘要：

  配体控制的反应性在过渡金属催化中起着重要作用，可以发现和开发大量有效的转化。然而，单个配体通常用于促进催化循环的所有步骤（例如，氧化加成、还原消除），这一要求使得配体设计具有挑战性并限制了其通用性，尤其是在中继不对称转化中。我们假设具有金属中心的多个配体可用于顺序促进多个催化步骤，从而通过简单配体的简单组合来结合互补的催化反应性。通过这种中继催化策略（L/L*），我们在此报告了第一个高度区域选择性和对映选择性远程加氢芳基化过程。3 )-H芳基化过程。

  DOI：

  10.1016/j.chempr.2021.10.015

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。
• A Four-Component Reaction for the Synthesis of Dioxadiazaborocines
  作者：Thomas Flagstad、Mette T. Petersen、Thomas E. Nielsen

  DOI：10.1002/anie.201502989

  日期：2015.7.13

  A four‐component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α‐hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron

  据报道，四价反应可合成杂环硼酸盐。现成的酰肼，α-羟基醛和两种正交反应的硼酸可在一个步骤中结合在一起，得到结构上不同的双环硼酸酯，称为二氧杂氮杂硼硼烷（DODA硼硼烷）。在这一非同寻常的过程中，一种硼酸以碳亲核体的形式发生反应，另一种以硼亲电子体的形式发生反应，从而以高收率提供具有多个立体中心的对映体和非对映体纯杂环硼酸酯。
• Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C
  作者：Ashabha I. Lansakara、S. V. Santhana Mariappan、F. Christopher Pigge

  DOI：10.1021/acs.joc.6b01269

  日期：2016.11.4

  bis(piperidine) ring system. Other key features of these model studies include development of an efficient ring-closing metathesis procedure to prepare macrocyclic derivatives of 3,4-disusbstituted pyridines, intramolecular cyclizations of alkylidene dihydropyridines to establish pyridine-substituted pyrrolidines and piperidines, successful homologation of pyridine-4-carboxaldehydes using formaldehyde dimethyl

  提出了模型研究结果，该研究表明了立体选择性合成路线为双（哌啶）生物碱异托乐明C的三环类似物。三环吡啶衍生物的脱芳香化反应得到亚烷基二氢吡啶（脱水碱）中间体，然后进行催化非均相氢化，以建立有关双（哌啶）环系统的正确相对立体化学。这些模型研究的其他关键特征包括开发一种有效的闭环复分解程序以制备3,4-取代的吡啶的大环衍生物，亚烷基二氢吡啶的分子内环化以建立吡啶取代的吡咯烷和哌啶，吡啶4的成功同源化使用甲醛二甲基硫代乙缩醛一氧化碳（FAMSO）的甲醛
• Structure-Based Design of Macrocyclic Factor XIa Inhibitors: Discovery of the Macrocyclic Amide Linker
  作者：James R. Corte、Tianan Fang、Honey Osuna、Donald J. P. Pinto、Karen A. Rossi、Joseph E. Myers、Steven Sheriff、Zhen Lou、Joanna J. Zheng、Timothy W. Harper、Jeffrey M. Bozarth、Yiming Wu、Joseph M. Luettgen、Dietmar A. Seiffert、Carl P. Decicco、Ruth R. Wexler、Mimi L. Quan

  DOI：10.1021/acs.jmedchem.6b01460

  日期：2017.2.9

  A novel series of macrocyclic FXIa inhibitors was designed based on our lead acyclic phenyl imidazole chemotype. Our initial macrocycles, which were double-digit nanomolar FXIa inhibitors, were further optimized with assistance from utilization of structure-based drug design and ligand bound X-ray crystal structures. This effort resulted in the discovery of a macrocyclic amide linker which was found

  基于我们的无环苯基咪唑基化学型，设计了一系列新的大环FXIa抑制剂。我们最初的大环化合物是两位数纳摩尔的FXIa抑制剂，在利用基于结构的药物设计和结合配体的X射线晶体结构的帮助下，得到了进一步的优化。这项工作导致发现了大环酰胺接头，该接头被发现与FXIa活性位点的Leu41的羰基形成关键的氢键，从而产生有效的FXIa抑制剂。以化合物16为例的大环FXIa系列的FXIa K i = 0.16 nM，在体外凝血试验中具有强大的抗凝活性（aPTT EC 1.5x = 0.27μM）和对相关血液凝结酶的优异选择性。
• [EN] INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014164428A1

  公开（公告）日：2014-10-09

  The disclosure generally relates to compounds of formula I, including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection. Formule (I)

  该披露通常涉及到公式I的化合物，包括用于治疗人类免疫缺陷病毒（HIV）感染的组合物和方法。该披露提供了HIV的新型抑制剂，包含这些化合物的药物组合物，以及使用这些化合物治疗HIV感染的方法。