2-(甲氧基羰基)乙基硼酸频那醇酯 | 1150561-77-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 2-(甲氧基羰基)乙基硼酸频那醇酯
• 中文别名: 3-（4,4,5,5-四甲基-[1,3,2]二氧杂环戊硼烷-2-yl）丙酸甲酯
• 英文名称: methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS: 1150561-77-5
• 化学式: C₁₀H₁₉BO₄
• 分子量: 214.069
• InChiKey: SWDXLJYTYJQFJI-UHFFFAOYSA-N

物化性质

• 沸点：
  242.7±23.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  -20°C，储存于惰性气体中

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(Methoxycarbonyl)ethylboronic acid, pinacol ester
Synonyms: Methyl 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)propionate

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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: 2-(Methoxycarbonyl)ethylboronic acid, pinacol ester
CAS number: 1150561-77-5

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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, under −20◦C.

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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: C10H19BO4
Molecular weight: 214.1

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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：

  2-(甲氧基羰基)乙基硼酸频那醇酯 在 1,1′-二(二环己基膦)二茂铁 、 叔丁基锂 、 palladium diacetate 、 potassium trifluoromethansulfonate 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 24.0h， 生成 methyl 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate
  参考文献：
  名称：

  钯催化格氏衍生硼“Ate”络合物与 C(sp2) 卤化物或三氟甲磺酸酯之间的连接交叉偶联：NaOTf 作为格氏活化剂和卤化物清除剂

  摘要：

  使用格氏试剂的催化对映选择性联合交叉偶联被证明能够以有效和高选择性的方式提供一系列非外消旋手性有机硼酸酯。三氟甲磺酸钠在促进该反应方面的用途有两个：它能够形成“ate”复合物并克服卤化物离子的催化抑制。

  DOI：

  10.1021/jacs.6b12663
• 作为产物：
  描述：

  联硼酸频那醇酯 在 1,3-bis(2,6-diisopropylphenylimidazol)-2-ylidene copper(I) dibenzoylmethanate 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 42.0h， 生成 2-(甲氧基羰基)乙基硼酸频那醇酯
  参考文献：
  名称：

  铜催化的一锅硼化醛缩醛化β-氟化物消除，从而将丙烯酸酯正式加成到羰基基团上

  摘要：

  在本文中，我们报道了2-氟丙烯酸甲酯与羰基化合物经铜催化的多米诺硼酸化/醛醇缩合，然后消除生成Morita–Baylis–Hillman（MBH）类似物。所描述的最佳条件显示与多种醛和酮相容。有效地合成了前所未有的源自酮的MBH加合物。

  DOI：

  10.1002/chem.201802023

文献信息

• Efficient synthesis of alkylboronic esters <i>via</i> magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides
  作者：Mahadev L. Shegavi、Abhishek Agarwal、Shubhankar Kumar Bose

  DOI：10.1039/d0gc00677g

  日期：——

  report a magnetically separable Cu nanocatalyst (Fe-DOPA-Cu) for the borylation of alkyl halides with alkoxy diboron reagents, providing alkylboronic esters in high yields, with broad functional group tolerance under mild reaction conditions. The procedure is also applicable to the borylation of benzyl chlorides and bromides. Radical clock experiments support a radical-mediated process. Easy recycling of

  我们报告了一种可磁分离的铜纳米催化剂（Fe-DOPA-Cu），用于烷基卤化物与烷氧基二硼试剂的硼酸酯化，可提供高产率的烷基硼酸酯，在温和的反应条件下具有宽泛的官能团耐受性。该方法也适用于苄基氯和溴化物的硼化。激进的时钟实验支持激进介导的过程。催化剂易于循环使用，最多十次运行不会造成活性显着下降。
• [EN] FUSED FURANS FOR THE TREATMENT OF HEPATITIS C<br/>[FR] FURANES FUSIONNÉS POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014159559A1

  公开（公告）日：2014-10-02

  The disclosure provides compounds of formula I or II, including their salts, as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV. [

  本公开提供了公式I或II的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物对丙型肝炎病毒（HCV）具有活性，可能对治疗HCV感染者有益。
• sp²−sp³ Hybridized Mixed Diboron: Synthesis, Characterization, and Copper-Catalyzed β-Boration of α,β-Unsaturated Conjugated Compounds
  作者：Ming Gao、Steven B. Thorpe、Webster L. Santos

  DOI：10.1021/ol901359n

  日期：2009.8.6

  A novel sp2−sp3 hybridized mixed diboron and its reactivity on the copper-catalyzed β-boration of α,β-unsaturated conjugated compounds to afford the corresponding β-borated compounds is reported. The presence of sp3-hybridized boron provides a mild β-boration condition in the absence of phosphine and base additives. Finally, our investigations demonstrate that the sp2-hybridized boron of the mixed

  报道了一种新颖的sp 2 -sp 3杂交的混合二硼及其在α，β-不饱和共轭化合物的铜催化的β-硼酸酯上的反应性，从而提供了相应的β-硼酸酯化的化合物。sp 3-杂化硼的存在在没有膦和碱添加剂的情况下提供了温和的β-硼化条件。最后，我们的研究表明混合二硼的sp 2-杂化硼被选择性转移到共轭底物的β-碳上。
• β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles
  作者：Marios Kidonakis、Michael Fragkiadakis、Manolis Stratakis

  DOI：10.1039/d0ob01806f

  日期：——

  Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via the intermediate formation of the labile silaboration adducts. This chemoselectivity pathway is complementary to the so far known analogous reaction catalyzed by other metals, where β-silylation occurs instead. β-Borylation

  共轭醛和酮与Me 2 PhSiBpin（pin：pinacolato）发生反应，这是通过不稳定形成的硅烷化加合物的中间形成，而Au纳米颗粒负载在TiO 2上，仅形成β-硼化产物。这种化学选择性途径是迄今为止由其他金属催化的类似反应的补充，在其他类似反应中发生了β-甲硅烷基化。在相同的反应条件下，在各种共轭羰基化合物中，pinBBpin也会发生β-硼化反应，这些共轭羰基化合物包括在其尝试的Au催化的合成中没有反应性的酯和酰胺。
• Basic CuCO₃ /ligand as a new catalyst for 'on water' borylation of Michael acceptors, alkenes and alkynes: application to the efficient asymmetric synthesis of β-alcohol type sitagliptin side chain
  作者：Gaj Stavber、Zdenko Časar

  DOI：10.1002/aoc.2957

  日期：2013.3

  The efficient 'on water' β‐borylation using bis(pinacolato)diboron agent was achieved with a newly developed catalytic system based on basic copper carbonate and various ligands. The catalytic system was used for β‐borylation of various Michael acceptors, alkenes and alkynes. The presented methodology was successfully applied to the novel synthesis of β‐alcohol type sitagliptin side chain precursor

  使用基于碱性碳酸铜和各种配体的新开发的催化系统，使用双（频哪醇）二硼剂实现了高效的“水上”β-硼化。催化体系用于各种迈克尔受体，烯烃和炔烃的β-硼化反应。所提出的方法已成功地通过水基高度对映选择性的β-硼化和随后的氧化过程成功地用于β-醇型西他列汀侧链前体的新型合成。版权所有©2013 John Wiley＆Sons，Ltd.