3-(哌啶-1-羰基)苯硼酸频哪酯 | 1073353-62-4

• 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-(哌啶-1-羰基)苯硼酸频哪酯
• 中文别名: 3-(哌啶-1-羰基)苯基硼酸频哪醇酯；3-(哌啶-1-羰基)苯硼酸频那醇酯
• 英文名称: 1-piperidinyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone
• 英文别名: piperidin-1-yl-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone；Piperidin-1-yl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone；piperidin-1-yl-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone
• CAS: 1073353-62-4
• 化学式: C₁₈H₂₆BNO₃
• 分子量: 315.22
• InChiKey: WACUHMBKMIVYKO-UHFFFAOYSA-N

物化性质

• 沸点：
  465.6±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(Piperidine-1-carbonyl)phenylboronic acid, pinacol ester
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: 3-(Piperidine-1-carbonyl)phenylboronic acid, pinacol ester
CAS number: 1073353-62-4

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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.
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: C18H26BNO3
Molecular weight: 315.2

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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-(哌啶-1-羰基)苯硼酸频哪酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三异丙基硅烷 、 四丁基溴化铵 、 cesium fluoride 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 20.0~120.0 ℃ 、1.72 MPa 条件下， 反应 1.5h， 生成 3-bromo-5-hydroxy-4-[3-(piperidine-1-carbonyl)-phenyl]-5H-furan-2-one
  参考文献：
  名称：

  Identification of new γ-hydroxybutenolides that preferentially inhibit the activity of mPGES-1

  摘要：

  Microsomal prostaglandin E-2 synthase-1 (mPGES-1) has been recognized as novel, promising drug target for anti-inflammatory and anticancer drugs. mPGES-1 catalyzes the synthesis of the inducible prostaglandin E-2 in response to pro-inflammatory stimuli, rendering this enzyme extremely interesting in drug discovery process owing to the drastic reduction of the severe side effects typical for traditional non-steroidal anti-inflammatory drugs. In the course of our investigations focused on this topic, we identified two interesting molecules bearing the gamma-hydroxybutenolide scaffold which potently inhibit the activity of mPGES-1. Notably, the lead compound 2c that inhibited mPGES-1 with IC50 = 0.9 mu M, did not affect other related enzymes within the arachidonic acid cascade. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.032
• 作为产物：
  描述：

  3-羧基苯硼酸 在 1-羟基苯并三唑 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 3-(哌啶-1-羰基)苯硼酸频哪酯
  参考文献：
  名称：

  Identification of new γ-hydroxybutenolides that preferentially inhibit the activity of mPGES-1

  摘要：

  Microsomal prostaglandin E-2 synthase-1 (mPGES-1) has been recognized as novel, promising drug target for anti-inflammatory and anticancer drugs. mPGES-1 catalyzes the synthesis of the inducible prostaglandin E-2 in response to pro-inflammatory stimuli, rendering this enzyme extremely interesting in drug discovery process owing to the drastic reduction of the severe side effects typical for traditional non-steroidal anti-inflammatory drugs. In the course of our investigations focused on this topic, we identified two interesting molecules bearing the gamma-hydroxybutenolide scaffold which potently inhibit the activity of mPGES-1. Notably, the lead compound 2c that inhibited mPGES-1 with IC50 = 0.9 mu M, did not affect other related enzymes within the arachidonic acid cascade. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.032

文献信息

• [EN] GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE GLYCOLATE OXYDASE POUR LE TRAITEMENT D'UNE MALADIE
  申请人：BIOMARIN PHARM INC

  公开号：WO2020257487A1

  公开（公告）日：2020-12-24

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与甘氧酸代谢缺陷相关的疾病或紊乱的方法，例如与甘氧酸氧化酶（GO）或草酸代谢变化相关的疾病或紊乱。这些疾病或紊乱包括与产生过多草酸相关的甘氧酸代谢紊乱，例如原发性高草酸尿症。
• Discovery of a series of 1H-pyrrolo[2,3-b]pyridine compounds as potent TNIK inhibitors
  作者：Bowen Yang、Qian Wu、Xiajuan Huan、Yingqing Wang、Yin Sun、Yueyue Yang、Tongchao Liu、Xin Wang、Lin Chen、Bing Xiong、Dongmei Zhao、Zehong Miao、Danqi Chen

  DOI：10.1016/j.bmcl.2020.127749

  日期：2021.2

  In an in-house screening, 1H-pyrrolo[2,3-b]pyridine scaffold was found to have high inhibition on TNIK. Several series of compounds were designed and synthesized, among which some compounds had potent TNIK inhibition with IC50 values lower than 1 nM. Some compounds showed concentration-dependent characteristics of IL-2 inhibition. These results provided new applications of TNIK inhibitors and new prospects

  在内部筛选中，发现1 H-吡咯并[2,3- b ]吡啶支架对TNIK具有高度抑制作用。设计并合成了一系列化合物，其中一些化合物具有强的TNIK抑制作用，IC 50值低于1 nM。一些化合物表现出浓度依赖性的IL-2抑制特性。这些结果提供了TNIK抑制剂的新应用以及TNIK作为药物靶标的新前景。
• <i>para</i> ‐Selective C−H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis
  作者：Lichen Yang、Kazuhiko Semba、Yoshiaki Nakao

  DOI：10.1002/anie.201701238

  日期：2017.4.18

  para‐Selective C−H borylation of benzamides and pyridines has been achieved by cooperative iridium/aluminum catalysis. A combination of iridium catalysts commonly employed for arene C−H borylation and bulky aluminum‐based Lewis acid catalysts provides an unprecedented strategy for controlling the regioselectivity of C−H borylation to give variously substituted (hetero)arylboronates, which are versatile

  苯甲酰胺和吡啶的对位C-H硼化已通过铱/铝协同催化实现。芳烃CH硼化中常用的铱催化剂和庞大的铝基路易斯酸催化剂的结合提供了一种空前的策略，可控制CH硼化的区域选择性，从而得到各种取代的（杂）芳基硼酸酯，它们是复杂的多用途合成中间体多取代的芳族化合物。
• Amide Effects in C−H Activation: Noncovalent Interactions with L-Shaped Ligand for <i>meta</i> Borylation of Aromatic Amides
  作者：Ranjana Bisht、Md Emdadul Hoque、Buddhadeb Chattopadhyay

  DOI：10.1002/anie.201809929

  日期：2018.11.26

  A new concept for the meta‐selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L‐shaped bifunctional ligand has been employed and engages in an O⋅⋅⋅K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction

  描述了芳族酰胺间选择性硼化的新概念。已经证明，尽管酯产生对硼烷基化，但是酰胺导致间硼烷基化。为了实现较高的间位选择性，使用了L型双功能配体，该配体与中度扭曲的酰胺羰基的氧原子发生O⋅⋅⋅K非共价相互作用。这种相互作用提供了对元CH活化/基化的特殊控制。
• Evaluation of aromatic 6-substituted thienopyrimidines as scaffolds against parasites that cause trypanosomiasis, leishmaniasis, and malaria
  作者：Jennifer L. Woodring、Gautam Patel、Jessey Erath、Ranjan Behera、Patricia J. Lee、Susan E. Leed、Ana Rodriguez、Richard J. Sciotti、Kojo Mensa-Wilmot、Michael P. Pollastri

  DOI：10.1039/c4md00441h

  日期：——

  The repurposing of human tyrosine kinase inhibitor scaffolds for generation of antiparasitic agents has provided new lead compounds for tropical diseases.

  人类酪氨酸激酶抑制剂骨架的再利用为生成抗寄生虫药物提供了新的引物化合物，为热带病提供了新的引物化合物。