1-Boc-吡唑-4-硼酸频哪醇酯 | 552846-17-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-Boc-吡唑-4-硼酸频哪醇酯
• 中文别名: 1-叔丁氧羰基-吡唑-4-硼酸频哪醇酯；1-叔丁氧羰基-4-(4,4,5,5-四氨乙基-1,3,2-二氧杂戊硼烷-2-基)吡唑；1-Boc-4-吡唑硼酸频哪醇酯；BOC-(吡唑-4-硼酸频哪醇酯)；1-BOC-吡唑-4-硼酸频哪酯；1-Boc-吡唑-4-硼酸频哪酯；1-叔丁氧羰基吡唑-4-硼酸频呐醇酯
• 英文名称: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate
• 英文别名: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate；1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid pinacol ester；1-Boc-pyrazole-4-boronic acid pinacol ester；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylic acid tert-butyl ester；4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole-1-carboxylic acid tert-butyl ester；tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-carboxylate；1-tert-butoxycarbonyl-4-(4,4,5,5-tetramethyl [1,3,2]dioxaborolan-2-yl)pyrazole；1-boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole；1-boc-4-pyrazole boronic acid pinacol ester；1-tert-butoxycarbonyl-pyrazole-4-boronic acid pinacol ester；1-Boc-pyrazol-4-boronic acid pinacol ester
• CAS: 552846-17-0
• 化学式: C₁₄H₂₃BN₂O₄
• 分子量: 294.159
• InChiKey: IPISOFJLWYBCAV-UHFFFAOYSA-N

物化性质

• 熔点：
  82-86 °C (lit.)
• 沸点：
  387.9±34.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 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：
  Refrigerator (±4°C)

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Boc-pyrazole-4-boronic 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: 1-Boc-pyrazole-4-boronic acid pinacol ester
CAS number: 552846-17-0

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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, refrigerated.
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: C14H23BN2O4
Molecular weight: 294.2

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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

制备方法与用途

性质

1-Boc-吡唑-4-硼酸频哪醇酯在常温常压下为白色或米白色固体。

用途

1-Boc-吡唑-4-硼酸频哪醇酯属于吡唑类衍生物，主要用作药物分子和生物活性分子的合成中间体。在合成过程中，吡唑环上的硼单元是一个非常实用的官能团转化前体，可以很容易地转化为氮原子或被氧化成羟基，或者通过Suzuki偶联反应连接上一个芳基或烷基基团。

合成方法

将5.8 mg（0.01 mmol，0.5 mol%）氯(1,5-环辛二烯)(1,1'-菲罗啉)铱四氢呋喃加合物和联硼酸频哪醇酯加入到一个敞口的反应瓶中，并用带隔膜的螺旋盖密封小瓶。通过真空下三次循环抽真空对小瓶进行氮气置换。

在第二个烧瓶中，制备0.344 mmol（0.050 mL，44.1 mg）频那醇硼烷在四氢呋喃（50 mL，0.0067 M）中的储备溶液。将储备溶液（1.4 mL，等当量的频那醇硼烷）注射到氯(1,5-环辛二烯)(1,1'-菲罗啉)铱四氢呋喃加合物和硼酸频哪醇酯的混合体系中，并将所得反应混合物加热至65℃反应1小时，直到形成暗红色溶液。随后加入0.336克1H-吡唑-1-甲酸叔丁酯，继续反应若干小时，通过GC、GC-MS和TLC监测反应进程。

当反应完成后，冷却小瓶并使用硅藻土过滤除去固体沉淀。将滤液在真空下蒸发旋干，用二氯甲烷溶解所得残余物，并通过柱色谱法（0:100至1:1乙酸乙酯与正己烷）提纯分离残余物，从而得到目标产物1-Boc-吡唑-4-硼酸频哪醇酯。

合成路线

图 1-Boc-吡唑-4-硼酸频哪醇酯的合成路线

反应信息

• 作为反应物：
  描述：

  1-Boc-吡唑-4-硼酸频哪醇酯 以80.2%的产率得到4-吡唑硼酸频哪醇酯
  参考文献：
  名称：

  一种吡唑-4-硼酸频哪醇酯的合成方法

  摘要：

  本发明公开了一种吡唑‑4‑硼酸频哪醇酯的合成方法，本发明反应时通过加入三甲苯作为稳定溶剂，降低了反应过程中出现副反应的情况，本发明操作简单、廉价，且易于纯化放大工业化生产的方法，弥补了目前4‑吡唑硼酸频哪醇酯的合成和纯化较困难等技术问题。

  公开号：

  CN110698506A
• 作为产物：
  描述：

  4-吡唑硼酸频哪醇酯 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-Boc-吡唑-4-硼酸频哪醇酯
  参考文献：
  名称：

  THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

  摘要：

  提供的方法是治疗一种由IDH1/2突变等位基因特征性存在的癌症，包括向需要此治疗的患者施用此处描述的化合物。

  公开号：

  US20150031627A1
• 作为试剂：
  描述：

  4-吡唑硼酸频哪醇酯 、 trans-4-{[4-[(5-chloro[1,3]thiazolo[5,4-b]pyridin-2-yl)amino]-6-(phenylmethyl)-2-pyrimidinyl]amino}cyclohexanol 在 四(三苯基膦)钯 caesium carbonate 、 1-Boc-吡唑-4-硼酸频哪醇酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以15%的产率得到trans-4-[(4-(phenylmethyl)-6-{[5-(1H-pyrazol-4-yl)[1,3]thiazolo[5,4-b]pyridin-2-yl]amino}-2-pyrimidinyl)amino]cyclohexanol
  参考文献：
  名称：

  [EN] PYRIMIDINE DERIVATIVES USED AS ITK INHIBITORS
  [FR] DÉRIVÉS DE PYRIMIDINE UTILISÉS COMME INHIBITEURS DE LTK

  摘要：

  本发明涉及某些新颖化合物。具体而言，本发明涉及以下公式（I）的化合物及其盐类。发明的化合物是激酶活性的抑制剂，特别是ltk活性的抑制剂。

  公开号：

  WO2010106016A1

文献信息

• PYRIMIDINYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES AND THEIR USE IN CANCER THERAPY
  申请人：Rewcastle Gordon William

  公开号：US20110009405A1

  公开（公告）日：2011-01-13

  Provided herein are pyrimidinyl and 1,3,5-triazinyl benzimidazoles of Formula I, and their pharmaceutical compositions, preparation, and use as agents or drugs for cancer therapy, either alone or in combination with radiation and/or other anticancer drugs.

  本文提供了式I的嘧啶基和1,3,5-三嗪基苯并咪唑化合物，以及它们的药物组合物、制备方法，以及作为抗癌治疗药物或药剂的用途，可以单独使用，也可以与放疗和/或其他抗癌药物联合使用。
• [EN] MERTK DEGRADERS AND USES THEREOF<br/>[FR] AGENTS DE DÉGRADATION DE MERTK ET LEURS UTILISATIONS
  申请人：KYMERA THERAPEUTICS INC

  公开号：WO2020010210A1

  公开（公告）日：2020-01-09

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用相同的方法。
• [EN] DIHYDROQUINOLIZINONES AS ANTIVIRALS<br/>[FR] DIHYDROQUINOLIZINONES À UTILISER EN TANT QU'ANTIVIRAUX
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2018154466A1

  公开（公告）日：2018-08-30

  Compounds, specifically hepatitis B virus and/or hepatitis D virus inhibitors, more specifically compounds that inhibit HBe antigen and HBs antigen in a subject, for the treatment of viral infections, and methods of preparing and using such compounds. Formula (I):

  化合物，具体来说是乙型肝炎病毒和/或丙型肝炎病毒抑制剂，更具体地说是抑制受试者体内HBe抗原和HBs抗原的化合物，用于治疗病毒感染，并且涉及制备和使用这类化合物的方法。化学式（I）:
• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150322063A1

  公开（公告）日：2015-11-12

  A compound represented by Formula [1] (in the formula, Z 1 represents N, CH, or the like; X 1 represents NH or the like; R 1 represents a heteroaryl group or the like; each of R 2 , R 3 , and R 4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R 5 represents a heteroaryl group or the like) or salt thereof.

  由式[1]表示的化合物（在该式中，Z表示N、CH或类似物；X表示NH或类似物；R表示杂环烷基或类似物；R2、R3和R4中的每一个表示氢原子、卤原子、烷氧基或类似物；R5表示杂环烷基或类似物）或其盐。
• [EN] QUINOLONE DERIVATIVES AS ANTIBACTERIALS<br/>[FR] DÉRIVÉS DE QUINOLONE COMME ANTIBACTÉRIENS
  申请人：NOVARTIS AG

  公开号：WO2016020836A1

  公开（公告）日：2016-02-11

  This invention is in the field of medicinal chemistry and relates to compounds, and pharmaceutical compositions thereof, that inhibit bacterial gyrase. The compounds are useful as inhibitors of bacterial gyrase activity and bacterial infections, and have the structure of Formula (I) as further described herein. The invention further provides pharmaceutical compositions comprising a compound of Formula (I) and methods of using the compounds and compositions to treat bacterial infections.

  这项发明属于药物化学领域，涉及抑制细菌旋转酶的化合物及其制药组合物，这些化合物可用作抑制细菌旋转酶活性和细菌感染的药物，并具有如下所述的Formula (I)的结构。该发明还提供了包含Formula (I)化合物的药物组合物，以及使用这些化合物和组合物治疗细菌感染的方法。