1-[3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)苄基]吡咯烷 | 884507-45-3

• 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: 1-[3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)苄基]吡咯烷
• 英文名称: 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pyrrolidine
• 英文别名: 1-[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]pyrrolidine
• CAS: 884507-45-3
• 化学式: C₁₇H₂₆BNO₂
• 分子量: 287.21
• InChiKey: AKQLICZDOCQKRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  C
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P260,P261,P264,P270,P271,P280,P301+P310+P330+P331,P303+P361+P353+P310,P304+P340+P310,P305+P351+P338+P310,P363,P405,P501
• 危险品运输编号：
  1760
• 危险性描述：
  H302,H312,H314,H332

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(Pyrrolidinomethyl)phenylboronic acid, pinacol ester
Synonyms: 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]pyrrolidine

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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-(Pyrrolidinomethyl)phenylboronic acid, pinacol ester
CAS number: 884507-45-3

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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: C17H26BNO2
Molecular weight: 287.2

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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：

  1-[3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)苄基]吡咯烷 、 4-溴苄胺盐酸盐 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 1.5h， 生成 [4-[3-(Pyrrolidin-1-ylmethyl)phenyl]phenyl]methanamine
  参考文献：
  名称：

  [EN] MODULATORS OF TOLL-LIKE RECEPTORS
  [FR] MODULATEURS DES RÉCEPTEURS DE TYPE TOLL (TLR)

  摘要：

  本申请涉及到TLRs的新型调节剂，包含这些化合物的组合物，以及包括这些化合物的治疗方法。

  公开号：

  WO2011031965A1
• 作为产物：
  描述：

  3-羟甲基苯硼酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium carbonate 、 双(2-二苯基磷苯基)醚 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 甲苯 为溶剂， 反应 26.0h， 生成 1-[3-(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)苄基]吡咯烷
  参考文献：
  名称：

  Synthesis of Amines with Pendant Boronic Esters by Borrowing Hydrogen Catalysis

  摘要：

  Amine alkylation reactions of alcohols have been performed in the presence of boronic ester groups to provide products which are known to have use as molecular sensors. The boronic ester moiety could be present in either the alcohol or amine starting material and was not compromised in the presence of a ruthenium catalyst.

  DOI：

  10.1021/ol402271a

文献信息

• MODULATORS OF TOLL-LIKE RECEPTORS
  申请人：Desai Manoj C.

  公开号：US20100143301A1

  公开（公告）日：2010-06-10

  Provided are modulators of TLRs of Formula II: pharmaceutically acceptable salts thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.

  提供了公式II的TLR调节剂：其药用盐，含有这类化合物的组合物，以及包括给予这类化合物的治疗方法。
• [EN] AMPK INHIBITORS<br/>[FR] INHIBITEURS D'AMPK
  申请人：UNIV SYDDANSK

  公开号：WO2019106087A1

  公开（公告）日：2019-06-06

  The 5'-AMP-activated protein kinase AMPK functions as a master switch to maintain cellular and whole-body energy homeostasis and abnormal activity profiles of AMPK may cause pathological disorders. The present invention relates to a series of compounds (I) based on a pyrrolo[2,3-c]pyridine and a thieno[2,3- c]pyridine scaffold as AMPK inhibitors. In particular, the present invention relates to the synthesis of such compounds and the medical use of such compounds.

  5'-AMP激活的蛋白激酶AMPK作为细胞和整体能量稳态的主要开关，AMPK的异常活性可能导致病理性疾病。本发明涉及一系列基于吡咯并[2,3-c]吡啶和噻吩[2,3-c]吡啶骨架的化合物(I)作为AMPK抑制剂。具体而言，本发明涉及这类化合物的合成以及这类化合物的医药用途。
• Discovery of GSK251: A Highly Potent, Highly Selective, Orally Bioavailable Inhibitor of PI3Kδ with a Novel Binding Mode
  作者：Kenneth Down、Augustin Amour、Niall A. Anderson、Nick Barton、Sebastien Campos、Edward P. Cannons、Cole Clissold、Maire A. Convery、John J. Coward、Kevin Doyle、Birgit Duempelfeld、Christopher D. Edwards、Michael D. Goldsmith、Jana Krause、David N. Mallett、Grant A. McGonagle、Vipulkumar K. Patel、James Rowedder、Paul Rowland、Andrew Sharpe、Srividya Sriskantharajah、Daniel A. Thomas、Douglas W. Thomson、Sorif Uddin、J. Nicole Hamblin、Edith M. Hessel

  DOI：10.1021/acs.jmedchem.1c01102

  日期：2021.9.23

  Optimization of a previously reported lead series of PI3Kδ inhibitors with a novel binding mode led to the identification of a clinical candidate compound 31 (GSK251). Removal of an embedded Ames-positive heteroaromatic amine by reversing a sulfonamide followed by locating an interaction with Trp760 led to a highly selective compound 9. Further optimization to avoid glutathione trapping, to enhance

  通过对先前报道的 PI3Kδ 抑制剂先导系列进行优化，采用新型结合模式，确定了临床候选化合物31 (GSK251)。通过逆转磺酰胺去除嵌入的 Ames 阳性杂芳胺，然后定位与 Trp760 的相互作用，产生高度选择性的化合物9 。进一步优化以避免谷胱甘肽捕获、增强效力和选择性以及优化口服药代动力学特征，发现了化合物31 (GSK215)，其具有较低的预测日剂量（45 mg，bid）和适合于大鼠的毒性特征。进一步发展。
• [EN] SUBSTITUTED NAPHTHALENE DIIMIDES AND THEIR USE<br/>[FR] DIIMIDES DE NAPHTALÈNE SUBSTITUÉS ET LEUR UTILISATION
  申请人：UCL BUSINESS PLC

  公开号：WO2020229840A1

  公开（公告）日：2020-11-19

  The present invention relates to naphthalene diimides, NDIs, and methods of synthesising them. The NDIs have DNA-quadruplex binding and stabilising activity, and potential in treatment of pancreatic, prostate, and other human cancers. The NDIs are a compound of Formula I:

  本发明涉及萘二酰亚胺（NDI）及其合成方法。NDI具有DNA四链体结合和稳定活性，在胰腺、前列腺和其他人类癌症的治疗中具有潜力。NDI是I式化合物：
• [EN] BICYCLIC COMPOUND AS HPK1 INHIBITOR AND APPLICATION THEREOF<br/>[FR] COMPOSÉ BICYCLIQUE SERVANT D'INHIBITEUR DE HPK1 ET SON UTILISATION<br/>[ZH] 作为HPK1抑制剂的双环类化合物及其应用
  申请人：JIANGSU SIMCERE PHARM CO LTD

  公开号：WO2022171034A1

  公开（公告）日：2022-08-18

  提供了式(I)所示化合物或其药学上可接受的盐、药物组合物及其制备方法，以及作为HPK1抑制剂的用途。