1-BOC-吡咯-3-硼酸频那醇酯 | 935278-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-BOC-吡咯-3-硼酸频那醇酯
• 中文别名: 1-BOC-吡咯-3-硼酸,频哪醇酯；1-BOC-吡咯-3-硼酸, 频哪醇 酯
• 英文名称: tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole-1-carboxylate
• CAS: 935278-73-2
• 化学式: C₁₅H₂₄BNO₄
• 分子量: 293.171
• InChiKey: STSRFVDSYZQVNM-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  381.3±34.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C，密封保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-pyrrole-3-boronic acid, pinacol ester
Synonyms: Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

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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: 1-BOC-pyrrole-3-boronic acid, pinacol ester
CAS number: 935278-73-2

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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, under −20◦C.
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: C15H24BNO4
Molecular weight: 293.2

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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-BOC-吡咯-3-硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 二异丁基氢化铝 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 环己烷 为溶剂， 反应 11.0h， 生成 tert-butyl 3-(3-(2-chloro-6-(trifluoromethyl)phenyl)-4-(hydroxymethyl)isoxazol-5-yl)-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  三取代异恶唑作为视黄酸受体相关孤儿受体γt的选择性变构配体的构效关系研究

  摘要：

  抑制核受体视黄酸受体相关孤儿受体 γt (RORγt) 是治疗自身免疫性疾病的一种有前景的策略。RORγt 在其配体结合域内具有变构结合位点，这为克服与正构调节剂相关的缺点提供了机会。最近，三取代的异恶唑被确定为一类新的变构 RORγt 反向激动剂。这种化学型为优化成选择性和有效的变构药物样分子提供了新的机会。在这里，我们结合基于结构的设计、X 射线晶体学和生化分析来探索异恶唑系列的构效关系。初始铅异恶唑（FM26) 得到优化，导致化合物的效力增加了约 10 倍（低 nM）、显着的细胞活性、有希望的药代动力学特性以及对过氧化物酶体增殖激活受体 γ 和法尼醇 X 受体的良好选择性。我们设想这项工作将成为加速开发异恶唑和其他新化学型的平台，以有效地变构靶向 RORγt。

  DOI：

  10.1021/acs.jmedchem.1c00475
• 作为产物：
  描述：

  频那醇硼烷 、 3-bromo-1-(tert-butoxycarbonyl)pyrrole 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 1-BOC-吡咯-3-硼酸频那醇酯
  参考文献：
  名称：

  用于钯催化的杂芳基卤化物和杂芳基硼酸和酯的 Suzuki-Miyaura 反应的高效单膦基催化剂

  摘要：

  已经开发了一种高活性和高效的催化剂体系，该体系源自钯预催化剂和单膦配体 1 或 2，用于杂芳基硼酸和酯的 Suzuki-Miyaura 交叉偶联反应。该方法允许以良好到优异的产率制备多种杂二芳基化合物，并且对于杂芳基氯化物以及受阻芳基和杂芳基卤化物的偶联显示出高水平的活性。还研究了控制某些杂环基序转化效率的特定因素。

  DOI：

  10.1021/ja068577p

文献信息

• Suzuki–Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
  作者：Shigehiro Asano、Seiji Kamioka、Yoshiaki Isobe

  DOI：10.1016/j.tet.2011.10.057

  日期：2012.1

  Suzuki–Miyaura cross-coupling reaction with 2-heteroarylboronic acids is generally challenging due to these acids easy decomposition. To overcome this problem, we developed a coupling method that uses 2-heteroaryl pinacol boronates in the presence of 1.0 mol % Pd(OAc)2 and 2.0 mol % S-Phos with 4 equiv amount of LiOH in dioxane and H2O at 80 °C for 30 min. This developed method allowed for the synthesis

  由于这些酸易于分解，因此与2-杂芳基硼酸的铃木-宫浦交叉偶联反应通常具有挑战性。为克服此问题，我们开发了一种偶合方法，该方法在1.0 mol％Pd（OAc）2和2.0 mol％S-Phos的存在下，在80％的二恶烷和H 2 O中于80摩尔下使用2-杂芳基频哪醇硼酸酯°C 30分钟。这种发达的方法允许从2-氯嘧啶基衍生物高产率地合成各种各样的2-杂芳基嘧啶，并且还可以用于由杂芳基氯化物制备各种联芳基衍生物。
• Microwave-Accelerated Iridium-Catalyzed Borylation of Aromatic C−H Bonds
  作者：Peter Harrisson、James Morris、Todd B. Marder、Patrick G. Steel

  DOI：10.1021/ol901306m

  日期：2009.8.20

  accelerates the Ir-catalyzed C−H borylation of aromatic substrates when compared with reactions carried out at the same temperature under standard heating conditions. Application to a one-pot single solvent process for tandem C−H borylation/Suzuki−Miyaura cross-coupling sequences using microwave-accelerated reactions gives fast and efficient access to a wide range of biaryl and heterobiaryl compounds.

  与在标准加热条件下在相同温度下进行的反应相比，微波加热可加速芳族底物的Ir催化CH硼化。通过微波加速反应应用于串联C–H硼酸酯化/ Suzuki-Miyaura交叉偶联序列的一锅单一溶剂工艺，可以快速，有效地获得各种联芳基和杂联芳基化合物。
• [EN] PEPTIDE MACROCYCLES AGAINST ACINETOBACTER BAUMANNII<br/>[FR] MACROCYCLES PEPTIDIQUES CONTRE ACINETOBACTER BAUMANNII
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017072062A1

  公开（公告）日：2017-05-04

  The present invention provides compounds of formula (I) wherein X1 to X8 and R1 to R8 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by Acinetobacter baumannii.

  本发明提供了式（I）的化合物，其中X1至X8和R1至R8如本文所述，以及其药学上可接受的盐。此外，本发明涉及制备式（I）的化合物，包括它们的药物组合物以及它们作为治疗由鲍曼不动杆菌引起的疾病和感染的药物的用途。
• Ligand-Based Design of Allosteric Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) Inverse Agonists
  作者：Femke A. Meijer、Richard G. Doveston、Rens M.J.M. de Vries、Gaël M. Vos、Alex A.A. Vos、Seppe Leysen、Marcel Scheepstra、Christian Ottmann、Lech-Gustav Milroy、Luc Brunsveld

  DOI：10.1021/acs.jmedchem.9b01372

  日期：2020.1.9

  Retinoic acid receptor-related orphan receptor γt (RORγt) is a nuclear receptor associated with the pathogenesis of autoimmune diseases. Allosteric inhibition of RORγt is conceptually new, unique for this specific nuclear receptor, and offers advantages over traditional orthosteric inhibition. Here, we report a highly efficient in silico-guided approach that led to the discovery of novel allosteric

  视黄酸受体相关的孤儿受体γt（RORγt）是与自身免疫性疾病发病机制相关的核受体。从理论上说，RORγt的变构抑制作用是新的，对于这种特定的核受体而言是独特的，并且比传统的正构抑制作用具有优势。在这里，我们报告了一种高效的计算机模拟方法，该方法导致发现了具有独特异恶唑化学型的新型变构RORγt反向激动剂。最有效的化合物25（FM26）在共激活剂募集试验中显示了亚微摩尔抑制作用，并有效降低了EL4细胞（RORγt活性的标志物）中IL-17a mRNA的产生。通过生化实验和与RORγt配体结合域的共结晶，证实了预计的25种变构作用模式。异恶唑化合物具有与其他变构配体相当的有希望的药代动力学性质，但具有更多样化的化学型。所采用的有效的基于配体的设计方法证明了其在产生化学多样性中用于RORγt的变构靶向的多功能性。
• 2-PYRIDONE ANTIMICROBIAL COMPOSITIONS
  申请人：Emergent Product Development Gaithersburg Inc.

  公开号：EP3034078A1

  公开（公告）日：2016-06-22

  Described are a series of 2-pyridone compounds as a potent and selective new class of type II topoisomerase inhibitors with broad-spectrum antimicrobial activity having the general formula (I); where R1, R2, X, and Y are defined herein Such compounds can be used in methods for treating an infection caused by a gram-positive pathogen, a gram-negative pathogen, or a drug-resistant strains thereof.

  描述了一系列2-吡啶酮化合物，作为一种强效且选择性的新型II型拓扑异构酶抑制剂，具有广谱抗菌活性，其通用公式为（I）；其中R1，R2，X和Y在本文中定义。这类化合物可用于治疗由革兰氏阳性病原体、革兰氏阴性病原体或耐药菌株引起的感染。