5-甲酰基呋喃-2-硼酸,频哪醇酯 | 273731-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-甲酰基呋喃-2-硼酸,频哪醇酯
• 英文名称: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
• CAS: 273731-82-1
• 化学式: C₁₁H₁₅BO₄
• 分子量: 222.049
• InChiKey: VSQZZPPWTRWPTM-UHFFFAOYSA-N

物化性质

• 熔点：
  40 - 43°C
• 沸点：
  338.1±27.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  储存条件：2-8℃，请保持干燥并密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Formylfuran-2-boronic acid, pinacol ester
Synonyms: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

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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-Formylfuran-2-boronic acid, pinacol ester
CAS number: 273731-82-1

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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.
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: C11H15BO4
Molecular weight: 222.0

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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-甲酰基呋喃-2-硼酸,频哪醇酯 在 palladium 10% on activated carbon 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 拉帕替尼
  参考文献：
  名称：

  [EN] A METHOD OF PRODUCING THE KEY INTERMEDIATE OF LAPATINIB SYNTHESIS
  [FR] PROCÉDÉ DE PRODUCTION DE L'INTERMÉDIAIRE CLÉ POUR LA SYNTHÈSE DE LAPATINIB

  摘要：

  本发明涉及一种化合物I的生产方法，包括将化合物III的碘衍生物与硼酸衍生物偶联，在溶剂中由适当的Pd催化剂催化，其中硼酸衍生物为一般式VII的环硼酸酯，其中R1、R2、R3和R4为H，或者为C1-C4（非）支链烷基，其中X为键或CR5R6，其中R5和R6为H，或者为C1-C4（非）支链烷基。该发明的其他方面包括环硼酸酯和化合物I的用途。

  公开号：

  WO2014059956A1
• 作为产物：
  描述：

  2-糠醛缩二乙醇 、 异丙醇频哪醇硼酸酯 在 正丁基锂 作用下， 以 乙二醇二甲醚 、 正己烷 为溶剂， 反应 11.5h， 生成 5-甲酰基呋喃-2-硼酸,频哪醇酯
  参考文献：
  名称：

  [EN] A METHOD OF PRODUCING THE KEY INTERMEDIATE OF LAPATINIB SYNTHESIS
  [FR] PROCÉDÉ DE PRODUCTION DE L'INTERMÉDIAIRE CLÉ POUR LA SYNTHÈSE DE LAPATINIB

  摘要：

  本发明涉及一种化合物I的生产方法，包括将化合物III的碘衍生物与硼酸衍生物偶联，在溶剂中由适当的Pd催化剂催化，其中硼酸衍生物为一般式VII的环硼酸酯，其中R1、R2、R3和R4为H，或者为C1-C4（非）支链烷基，其中X为键或CR5R6，其中R5和R6为H，或者为C1-C4（非）支链烷基。该发明的其他方面包括环硼酸酯和化合物I的用途。

  公开号：

  WO2014059956A1

文献信息

• Synthesis and biological evaluation of 6-(pyrimidin-4-yl)-1H-pyrazolo[4,3-b]pyridine derivatives as novel dual FLT3/CDK4 inhibitors
  作者：Xiandeng Li、Tao Yang、Mengshi Hu、Yingxue Yang、Minghai Tang、Dexin Deng、Kongjun Liu、Suhong Fu、Yan Tan、Huan Wang、Yong Chen、Chufeng Zhang、Yong Guo、Bin Peng、Wenting Si、Zhuang Yang、Lijuan Chen

  DOI：10.1016/j.bioorg.2022.105669

  日期：2022.4

  to play a significant role in tumor therapy. Herein, based on the previously reported JAK2/FLT3 inhibitor 18e, we described the synthesis, structure–activity relationship and biological evaluation of a series of unique 6-(pyrimidin-4-yl)-1H-pyrazolo[4,3-b]pyridine derivatives that inhibited FLT3 and CDK4 kinases. The optimized compound 23k exhibited low nanomolar range activities with IC50 values of

  FMS 样酪氨酸激酶 3 (FLT3) 和细胞周期蛋白依赖性激酶 4/6 (CDK4/6) 抑制剂已被证明在肿瘤治疗中发挥重要作用。在此，基于先前报道的 JAK2/FLT3 抑制剂18e，我们描述了一系列独特的 6-(pyrimidin-4-yl)-1 H - pyrazolo[4,3- b ]吡啶衍生物，可抑制 FLT3 和 CDK4 激酶。优化的化合物23k表现出低纳摩尔范围的活性，对 FLT3 和 CDK4 的 IC 50值分别为 11 和 7 nM。在 MV4-11 异种移植肿瘤模型中，23k 在 200 mg/kg 剂量下的肿瘤生长抑制率为67 %，表明23k具有抗肿瘤治疗作用。
• Rh^III-Catalyzed Direct Heteroarylation of C(sp³)–H and C(sp²)–H Bonds in Heterocycles with <i>N</i>-Heteroaromatic Boronates
  作者：Huai-Wei Wang、Jia-Xue Wu、Yu-Han Qiao、Yong-Fei Li、Da-Cheng Li、Jian-Min Dou、Qing-Xia Yao、Yi Lu

  DOI：10.1021/acs.orglett.1c02546

  日期：2021.9.17

  Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)–H and C(sp2)–H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents

  在此，我们公开了用有机硼试剂使杂环中的 C(sp 3 )-H 和 C(sp 2 )-H 键发生 Rh III催化的杂芳基化反应。该协议显示出高效率和出色的官能团耐受性。一系列具有强配位原子的杂环硼酸酯，包括吡啶、嘧啶、吡唑、噻吩和呋喃衍生物，可广泛用作偶联剂。直接杂芳基化方法可以在合成具有多个杂环的药物分子方面提供潜在的应用。
• Aerobic Visible-Light-Driven Borylation of Heteroarenes in a Gel Nanoreactor
  作者：Jorge C. Herrera-Luna、David Díaz Díaz、Alex Abramov、Susana Encinas、M. Consuelo Jiménez、Raúl Pérez-Ruiz

  DOI：10.1021/acs.orglett.1c00451

  日期：2021.3.19

  Heteroarene boronate esters constitute valuable intermediates in modern organic synthesis. As building blocks, they can be further applied to the synthesis of new materials, since they can be easily transformed into any other functional group. Efforts toward novel and efficient strategies for their preparation are clearly desirable. Here, we have achieved the borylation of commercially available heteroarene

  杂芳烃硼酸酯是现代有机合成中有价值的中间体。作为积木，它们可以进一步应用于新材料的合成，因为它们可以很容易地转化为任何其他官能团。显然需要努力为它们的制备提供新颖和有效的策略。在这里，我们在易于使用的凝胶纳米反应器中在非常温和的条件下实现了市售杂芳烃卤化物的硼化。它在室温下在无光催化剂和有氧条件下使用可见光作为能源，使该协议非常有吸引力。凝胶网络提供了足够的稳定微环境以支持广泛的底物范围，包括呋喃、噻吩、硒酚和吡咯硼酸酯。
• Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction
  作者：Akitake Yamaguchi、Sherif J. Kaldas、Solomon D. Appavoo、Diego B. Diaz、Andrei K. Yudin

  DOI：10.1039/c9cc05934b

  日期：——

  Macrocyclization of linear peptide precursors using the Petasis borono-Mannich reaction affords a diverse range of macrocycles with an endocyclic amine. Analysis of the corresponding macrocyclic structures underscores that the hydrogen bond between an endocyclic amine and the adjacent amide NH is a powerful control element for conformationally homogenous peptide macrocycles.

  使用Petasis borono-Mannich反应对线性肽前体进行大环化可提供带有环内胺的各种大环。对相应大环结构的分析强调，环内胺与相邻酰胺NH之间的氢键是构象均一的肽大环的强大控制元素。
• Highly Lewis Acidic Arylboronate Esters Capable of Colorimetric Turn-On Response
  作者：Alexander Oehlke、Alexander A. Auer、Katja Schreiter、Nadine Friebe、Stefan Spange

  DOI：10.1002/chem.201500835

  日期：2015.12.1

  A series of boronate‐π‐acceptor compounds containing different types of π bridges (1,4‐phenylen or thien‐2,5‐diyl or furan‐2,5‐diyl) that link the switchable boronate ester group with the efficient TCF acceptor group (TCF=2‐dicyanomethylen‐3‐cyano‐4,5,5‐trimethyl‐2,5‐dihydrofuran) has been synthesized. A TCF chromophore of this type undergoes transition to a donor‐π‐acceptor compound upon coordination

  一系列包含不同类型π桥（1,4-亚苯基或噻吩-2,5-二基或呋喃-2,5-二基）的硼酸酯-π-受体化合物，这些化合物将可转换的硼酸酯基团与有效的TCF受体相连已合成（TCF = 2-二氰基亚甲基-3-氰基-4,5,5-三甲基-2,5-二氢呋喃）基团。这种类型的TCF发色团在Lewis酸性硼中心的Lewis碱配位后会转变为供体-π-受体化合物，并伴随着分子内电荷转移相互作用的增强。路易斯酸的特性已通过光谱测量（UV / Vis，NMR光谱）以及DFT和从头算的方法进行了研究。结果表明，TCF受体基团和与硼原子直接键合的噻吩或呋喃π桥共同提高了路易斯酸度。 CH 2 Cl 2中的8 M -1。除了较强的氟化硼结合基序，路易斯相互作用还与较弱的路易斯碱（例如吡啶或脂族醇）发生。发色和路易斯酸性性质的独特结合是在复合物形成后可检测到的强烈比色开启反应的原因。