[3-(2-carboxyvinyl)phenyl]boronic acid | 216144-91-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [3-(2-carboxyvinyl)phenyl]boronic acid
• 英文别名: (2E)-3-[3-(Dihydroxyboranyl)phenyl]prop-2-enoic acid；3-(3-boronophenyl)prop-2-enoic acid
• CAS: 216144-91-1
• 化学式: C₉H₉BO₄
• 分子量: 191.979
• InChiKey: QCHIEOGZUMAQKI-UHFFFAOYSA-N

物化性质

• 熔点：
  218-221°C
• 沸点：
  454.1±47.0 °C(Predicted)
• 密度：
  1.33±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)：
  -0.54
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(trans-2-Carboxyvinyl)phenylboronic acid
Product Name:
Synonyms: 3-Boronocinnamic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
3-(trans-2-Carboxyvinyl)phenylboronic acid
Ingredient name:
CAS number: 216144-91-1

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

---

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.

---

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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H9BO4
Molecular weight: 192.0

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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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  [3-(2-carboxyvinyl)phenyl]boronic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、144.79 kPa 条件下， 反应 5.0h， 以90%的产率得到3-(2-羧基乙基)苯基硼酸
  参考文献：
  名称：

  苯硼酸衍生物作为有效的线索在过表达KPC-2的临床菌株中起作用：对抗细菌耐药性的步骤

  摘要：

  对几乎所有可用抗生素具有耐药性的多药耐药（MDR）病原体的出现和传播在临床治疗中构成了重大威胁。其中，肺炎克雷伯菌过度表达KPC-2碳青霉烯酶的临床分离株是最令人担忧的，将细菌耐药性扩展到最后一种碳青霉烯类。在这项研究中，我们研究了小苯基硼酸衍生物在KPC-2活性位点的分子识别要求。针对KPC-2设计并测试了四种新的苯基硼酸衍生物。对于最活跃的分子，尽管其化学结构简单，但仍可实现纳摩尔亲和力。新的衍生物恢复了过表达KPC-2的临床菌株对美洛培南的敏感性。此外，在细胞活力测定中未检测到细胞毒性，这进一步验证了设计的潜在顾客。在高分辨率下获得了两种最佳抑制剂结合KPC-2的晶体学二元复合物。慢结合，时间依赖性抑制，并全面研究了KPC-2中的相互作用几何。这项研究最终将导致优化和开发更有效的KPC-2抑制剂。

  DOI：

  10.1002/cmdc.201700788

文献信息

• A DNA‐Encoded Chemical Library Incorporating Elements of Natural Macrocycles
  作者：Cedric J. Stress、Basilius Sauter、Lukas A. Schneider、Timothy Sharpe、Dennis Gillingham

  DOI：10.1002/anie.201902513

  日期：2019.7.8

  Here we show a seven‐step chemical synthesis of a DNA‐encoded macrocycle library (DEML) on DNA. Inspired by polyketide and mixed peptide‐polyketide natural products, the library was designed to incorporate rich backbone diversity. Achieving this diversity, however, comes at the cost of the custom synthesis of bifunctional building block libraries. This study outlines the importance of careful retrosynthetic

  在这里，我们展示了在DNA上进行DNA编码的大环文库（DEML）的七步化学合成。受聚酮化合物和肽-聚酮化合物混合天然产物的启发，该文库旨在整合丰富的骨架多样性。但是，要实现这种多样性，就要以双功能构件块库的定制合成为代价。这项研究概述了在DNA编码文库中仔细进行逆向合成设计的重要性，同时揭示了需要新的DNA合成方法的领域。
• MONOMERS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
  申请人：Barany Francis

  公开号：US20140194383A1

  公开（公告）日：2014-07-10

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer, (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.

  本发明描述了在水中介质中与一个、两个、三个或更多其他单体接触时能够形成具有生物学用途的多聚体的单体。在一方面，这样的单体可能能够在水介质中（例如，体内）与另一个单体结合形成多聚体（例如，二聚体）。考虑的单体可能包括一个配体部分、一个连接元素和一个连接器元素，连接器元素连接配体部分和连接元素。在水介质中，这样的考虑单体可能通过每个连接元素相互连接，因此可能能够实质上同时调节一个或多个生物分子，例如，调节蛋白质上的两个或多个结合域，或者调节不同蛋白质上的结合域。
• [EN] PHTHALAZINE DERIVATIVES PHOSPHODIESTERASE 4 INHIBITORS<br/>[FR] DERIVES DE PHTHALAZINE UTILISES COMME INHIBITEURS DE LA PHOSPHODIESTERASE 4
  申请人：ZAMBON SPA

  公开号：WO2004056798A1

  公开（公告）日：2004-07-08

  Compounds of formula (I) wherein R is methyl or difluoromethyl; X is a methylene group, ethylene, -CH=CH-, -O-CH2-, -O-(CH2)2, -O-(CH2)3-, -NH-SO2-(CH2)3-, -NH-CO-(CH2)2-, -NH-CO-(CH2)3-, N-(ethane-sulfonylamino) pyperazinyl, the N-oxidised derivatives of -CH2-CH-NH2 | the compounds of formula I and the pharmaceutically acceptable salts thereof are described.The compounds of formula I are PDE 4 inhibitors.

  式（I）的化合物中，其中R是甲基或二氟甲基；X是一个亚甲基基团，乙烯基，-CH=CH-，-O-CH2-，-O-(CH2)2，-O-(CH2)3-，-NH-SO2-(CH2)3-，-NH-CO-(CH2)2-，-NH-CO-(CH2)3-，N-(乙烷磺酰氨基)吡嗪基，-CH2-CH-NH2的N-氧化衍生物 | 描述了式I的化合物及其药用盐。式I的化合物是PDE 4抑制剂。
• BROMODOMAIN LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
  申请人：Coferon, Inc.

  公开号：US20140243286A1

  公开（公告）日：2014-08-28

  Described herein are monomers capable of forming a biologically useful multimer when in contact with one, two, three or more other monomers in an aqueous media. In one aspect, such monomers may be capable of binding to another monomer in an aqueous media (e.g. in vivo) to form a multimer (e.g. a dimer). Contemplated monomers may include a ligand moiety, a linker element, and a connector element that joins the ligand moiety and the linker element. In an aqueous media, such contemplated monomers may join together via each linker element and may thus be capable of modulating one or more biomolecules substantially simultaneously, e.g., modulate two or more binding domains on a protein or on different proteins.

  本文介绍了一种单体，当在水介质中与一个、两个、三个或更多其他单体接触时，能够形成生物上有用的多聚体。在其中一方面，这种单体可以在水介质中（例如在体内）与另一个单体结合形成多聚体（例如二聚体）。考虑到的单体可能包括配体基团、连接元素和连接配体基团和连接元素的连接元素。在水介质中，这些考虑到的单体可以通过每个连接元素连接在一起，因此可以同时调节一个或多个生物分子，例如调节蛋白质或不同蛋白质上的两个或更多结合结构域。
• Phenylboronic Acid Derivatives as Validated Leads Active in Clinical Strains Overexpressing KPC-2: A Step against Bacterial Resistance
  作者：Giuseppe Celenza、Mattia Vicario、Pierangelo Bellio、Pasquale Linciano、Mariagrazia Perilli、Antonio Oliver、Jesús Blazquez、Laura Cendron、Donatella Tondi

  DOI：10.1002/cmdc.201700788

  日期：2018.4.6

  significant threat in clinical therapy. Among them, Klebsiella pneumoniae clinical isolates overexpressing KPC‐2 carbapenemase are the most worrisome, extending bacterial resistance to last‐resort carbapenems. In this study, we investigate the molecular recognition requirements in the KPC‐2 active site by small phenylboronic acid derivatives. Four new phenylboronic acid derivatives were designed and tested

  对几乎所有可用抗生素具有耐药性的多药耐药（MDR）病原体的出现和传播在临床治疗中构成了重大威胁。其中，肺炎克雷伯菌过度表达KPC-2碳青霉烯酶的临床分离株是最令人担忧的，将细菌耐药性扩展到最后一种碳青霉烯类。在这项研究中，我们研究了小苯基硼酸衍生物在KPC-2活性位点的分子识别要求。针对KPC-2设计并测试了四种新的苯基硼酸衍生物。对于最活跃的分子，尽管其化学结构简单，但仍可实现纳摩尔亲和力。新的衍生物恢复了过表达KPC-2的临床菌株对美洛培南的敏感性。此外，在细胞活力测定中未检测到细胞毒性，这进一步验证了设计的潜在顾客。在高分辨率下获得了两种最佳抑制剂结合KPC-2的晶体学二元复合物。慢结合，时间依赖性抑制，并全面研究了KPC-2中的相互作用几何。这项研究最终将导致优化和开发更有效的KPC-2抑制剂。