3-(吡咯烷-1-羰基)苯硼酸频哪酯 | 1073353-61-3

• 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: 3-(吡咯烷-1-羰基)苯硼酸频哪酯
• 中文别名: 3-（1-吡咯烷基羰基）苯硼酸频哪醇酯；3-吡咯烷羰基苯硼酸频那醇酯；3-(吡咯烷-1-羰基)苯硼酸频哪酯,97%
• 英文名称: pyrrolidin-1-yl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone
• 英文别名: pyrrolidin-1-yl-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanone
• CAS: 1073353-61-3
• 化学式: C₁₇H₂₄BNO₃
• mdl: MFCD09027086
• 分子量: 301.193
• InChiKey: CLPFNNNIZHMNPT-UHFFFAOYSA-N

物化性质

• 熔点：
  92-98 °C
• 沸点：
  452.1±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.588
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Pyrrolidinylcarbonylphenylboronic 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-Pyrrolidinylcarbonylphenylboronic acid, pinacol ester
CAS number: 1073353-61-3

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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: C17H24BNO3
Molecular weight: 301.2

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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-(吡咯烷-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-(pyrrolidine-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-碘苯甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 草酰氯 、 potassium acetate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-(吡咯烷-1-羰基)苯硼酸频哪酯
  参考文献：
  名称：

  具有酰胺远程碱性官能团的咪唑类卡宾配体 及其合成方法与应用

  摘要：

  本发明公开了一种具有碱性远程官能团的咪唑类卡宾配体，其为式(1)所示的化合物，可以与金形成稳定的金属配合物，用于催化环化反应、重排反应、亲核加成反应等。本发明提供了一种新型咪唑类卡宾配体及其金属配合物的合成路线，实现了炔烃亲核加成的简单高效反应。这种NHC‑Au催化剂既具有以金为中心的Lewis酸活化中心，同时又具有以碱性基团为中心的碱活化中心，利用一价金络合物(配体‑金‑底物)的独特线性结构能形成受阻Lewis酸碱对，从而实现碱性官能团和亲核试剂或底物之间的有益相互作用，达到催化体系对反应过渡态的双重协同活化作用。

  公开号：

  CN110483503B

文献信息

• 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。
• 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。
• Discovery and SAR of pyrrolo[2,1-f][1,2,4]triazin-4-amines as potent and selective PI3Kδ inhibitors
  作者：Rajeev S. Bhide、James Neels、Lan-Ying Qin、Zheming Ruan、Sylwia Stachura、Carolyn Weigelt、John S. Sack、Kevin Stefanski、Xiaomei Gu、Jenny H. Xie、Christine B. Goldstine、Stacey Skala、Donna L. Pedicord、Stefan Ruepp、T.G. Murali Dhar、Percy H. Carter、Luisa M. Salter-Cid、Michael A. Poss、Paul Davies

  DOI：10.1016/j.bmcl.2016.07.047

  日期：2016.9

  Aberrant Class I PI3K signaling is a key factor contributing to many immunological disorders and cancers. We have identified 4-amino pyrrolotriazine as a novel chemotype that selectively inhibits PI3Kδ signaling despite not binding to the specificity pocket of PI3Kδ isoform. Structure activity relationship (SAR) led to the identification of compound 30 that demonstrated efficacy in mouse Keyhole Limpet

  异常的I类PI3K信号传导是导致许多免疫性疾病和癌症的关键因素。我们已经确定4-氨基吡咯并三嗪是一种新型化学型，尽管不结合PI3Kδ同工型的特异性口袋，但选择性抑制PI3Kδ信号传导。结构活性关系（SAR）导致了对化合物30的鉴定，该化合物在小鼠Keyhole Limpet血蓝蛋白（KLH）和胶原诱导的关节炎（CIA）模型中显示出功效。
• 一种吡啶并[1,2-a][1,2,4]三唑卡宾配体及 其合成方法与应用
  申请人：浙江工业大学

  公开号：CN110483502B

  公开（公告）日：2020-11-13

  本发明提供了一种吡啶并[1,2‑a][1,2,4]三唑卡宾配体及其合成方法与应用，所述的如式Ⅴ吡啶并[1,2‑a][1,2,4]三唑卡宾配体与金形成吡啶并[1,2‑a][1,2,4]三唑卡宾‑金配合物能够应用于炔烃催化加成反应，具有Lewis酸/碱双重活化中心，能够依托其双活化中心的“协同活化作用”，从而实现常规配体所不能或无法达到的催化效果，能够极大地加速亲核试剂对重键的加成反应。
• <i>para</i> ‐Selective Radical Trifluoromethylation of Benzamide Derivatives via Iminium Intermediates
  作者：Zhanyong Tang、Ke Mo、Xiaoqiang Ma、Jialin Huang、Depeng Zhao

  DOI：10.1002/anie.202208089

  日期：2022.9.5

  A para-selective C−H trifluoromethylation of benzamide derivatives was developed that makes use of iminium intermediates. The iminium species, formed in situ from Tf2O, pyridine and amides, feature greatly enhanced reactivity at the para-position towards radical-type nucleophilic C−H trifluoromethylation.

  使用亚胺中间体开发了苯甲酰胺衍生物的对位选择性 C-H 三氟甲基化。由 Tf 2 O、吡啶和酰胺原位形成的亚胺物种在对位上对自由基型亲核 C-H 三氟甲基化具有显着增强的反应性。