3-(Boc-氨基)-5-羧基苯硼酸 | 913835-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(Boc-氨基)-5-羧基苯硼酸
• 中文别名: 3-(N-BOC-氨基)-5-羧基苯基硼酸
• 英文名称: 3-borono-5-((tert-butoxycarbonyl)amino)benzoic acid
• 英文别名: 3-borono-5-[(2-methylpropan-2-yl)oxycarbonylamino]benzoic acid
• CAS: 913835-72-0
• 化学式: C₁₂H₁₆BNO₆
• 分子量: 281.073
• InChiKey: DDZVPNHBJRCXEI-UHFFFAOYSA-N

物化性质

• 熔点：
  >300

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(N-Boc-Amino)-5-carboxyphenylboronic acid
Product Name:
Synonyms: 3-Borono-5-(tert-butoxycarbonylamino)benzoic 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-(N-Boc-Amino)-5-carboxyphenylboronic acid
Ingredient name:
CAS number: 913835-72-0

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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.

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H16BNO6
Molecular weight: 281.1

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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, nitrogen oxides.

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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-(Boc-氨基)-5-羧基苯硼酸 在 N-甲基咪唑 、 盐酸 、 N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.25h， 生成 (R)-(3-(6-chloro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamido)-5-((1-cyclohexyl-2-(methylamino)-2-oxoethyl)-carbamoyl)phenyl)boronic acid
  参考文献：
  名称：

  从新型 DNA 编码库中发现基于硼酸的选择性 PDE3B 抑制剂并进行 SAR 研究

  摘要：

  人类遗传证据表明 PDE3B 与代谢和血脂异常表型相关。多种PDE3家族选择性抑制剂已获得FDA批准用于多种适应症；然而，考虑到心脏中不良的致心律失常作用，对密切相关的家族成员（例如 PDE3A；48% 同一性）的 PDE3B 抑制的选择性是开发 PDE3B 疗法的关键考虑因素。 PDE3B 相对于 PDE3A 的选择性可以通过多种方式实现，包括化合物固有的特性或组织选择性靶向。 PDE3A 和 B 之间的高活性位点同源性 (>95%) 是在活性位点获得选择性的巨大障碍；然而，在高通量筛选中利用具有高分子多样性的文库可能会发现选择性化学物质。在此，我们采用 DNA 编码库筛选来鉴定 PDE3B 选择性抑制剂，并鉴定出结合在活性位点的有效且选择性的硼酸化合物。

  DOI：

  10.1021/acs.jmedchem.3c01562

文献信息

• Discovery and SAR Study of Boronic Acid-Based Selective PDE3B Inhibitors from a Novel DNA-Encoded Library
  作者：Ann M. Rowley、Gang Yao、Logan Andrews、Aaron Bedermann、Ross Biddulph、Ryan Bingham、Jennifer J. Brady、Rachel Buxton、Ted Cecconie、Rona Cooper、Adam Csakai、Enoch N. Gao、Melissa C. Grenier-Davies、Meghan Lawler、Yiqian Lian、Justyna Macina、Colin Macphee、Lisa Marcaurelle、John Martin、Patricia McCormick、Rekha Pindoria、Martin Rauch、Warren Rocque、Yingnian Shen、Lisa M. Shewchuk、Michael Squire、Will Stebbeds、Westley Tear、Xin Wang、Paris Ward、Shouhua Xiao

  DOI：10.1021/acs.jmedchem.3c01562

  日期：2024.2.8

  between PDE3A and B represents a massive obstacle for obtaining selectivity at the active site; however, utilization of libraries with high molecular diversity in high throughput screens may uncover selective chemical matter. Herein, we employed a DNA-encoded library screen to identify PDE3B-selective inhibitors and identified potent and selective boronic acid compounds bound at the active site.

  人类遗传证据表明 PDE3B 与代谢和血脂异常表型相关。多种PDE3家族选择性抑制剂已获得FDA批准用于多种适应症；然而，考虑到心脏中不良的致心律失常作用，对密切相关的家族成员（例如 PDE3A；48% 同一性）的 PDE3B 抑制的选择性是开发 PDE3B 疗法的关键考虑因素。 PDE3B 相对于 PDE3A 的选择性可以通过多种方式实现，包括化合物固有的特性或组织选择性靶向。 PDE3A 和 B 之间的高活性位点同源性 (>95%) 是在活性位点获得选择性的巨大障碍；然而，在高通量筛选中利用具有高分子多样性的文库可能会发现选择性化学物质。在此，我们采用 DNA 编码库筛选来鉴定 PDE3B 选择性抑制剂，并鉴定出结合在活性位点的有效且选择性的硼酸化合物。