2-(叔丁氧基甲基)苯硼酸 | 373384-12-4

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(叔丁氧基甲基)苯硼酸
• 英文名称: 2-(tert-butoxymethyl)phenylboronic acid
• 英文别名: [2-[(2-methylpropan-2-yl)oxymethyl]phenyl]boronic acid
• CAS: 373384-12-4
• 化学式: C₁₁H₁₇BO₃
• 分子量: 208.065
• InChiKey: MKTUWARSDLQBAL-UHFFFAOYSA-N

物化性质

• 沸点：
  336.1±44.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R22
• 海关编码：
  2931900090
• 危险性防范说明：
  P264,P270,P301+P312+P330,P501
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(tert-Butoxymethyl)phenylboronic acid
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: 2-(tert-Butoxymethyl)phenylboronic acid
CAS number: 373384-12-4

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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, 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: C11H17BO3
Molecular weight: 208.1

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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.

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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：

  2-(叔丁氧基甲基)苯硼酸 在 palladium diacetate 三氟甲磺酸三甲基硅酯 、 三溴化磷 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 methyl 4-(2-bromomethylbenzyl)benzoate
  参考文献：
  名称：

  Substituted imidazoline-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof

  摘要：

  该发明涉及式(I)的化合物，其中基团R和R'、A、D、E、G、L、p以及R1到R10具有所述含义，以及它们的生理相容盐。所述化合物适用于作为抗肥胖药物。

  公开号：

  US20110112097A1

文献信息

• SUBSTITUTED PYRROLOPYRIDINES AND PYRAZOLOPYRIDINES AS KINASE MODULATORS
  申请人：Blaney Jeffrey M.

  公开号：US20090005356A1

  公开（公告）日：2009-01-01

  Provided herein are substituted pyrrolopyridine heterocycles and substituted pyrazolopyridine heterocycles, pharmaceutical compositions comprising said heterocycles and methods of using said heterocycles in the treatment of disease. The heterocycles disclosed herein function as kinase modulators and have utility in the treatment of diseases such as cancer, allergy, asthma, inflammation, obstructive airway disease, autoimmune diseases, metabolic disease, infection, CNS disease, brain tumor, obesity, asthma, hematological disorder, degenerative neural disease, cardiovascular disease, or disease associated with angiogenesis, neovascularization, or vasculogenesis.

  本文提供了取代的吡咯吡啶杂环和取代的吡唑吡啶杂环，以及包含这些杂环的制药组合物以及使用这些杂环治疗疾病的方法。本文所披露的杂环可作为激酶调节剂，并在治疗癌症、过敏、哮喘、炎症、阻塞性呼吸道疾病、自身免疫疾病、代谢性疾病、感染、中枢神经系统疾病、脑肿瘤、肥胖症、哮喘、血液疾病、退行性神经疾病、心血管疾病或与血管生成、新生血管或血管生成有关的疾病中具有实用价值。
• Substituted pyrrolopyridines and pyrazolopyridines as kinase modulators
  申请人：SGX Pharmaceuticals, Inc.

  公开号：US08158647B2

  公开（公告）日：2012-04-17

  Provided herein are substituted pyrrolopyridine heterocycles and substituted pyrazolopyridine heterocycles, pharmaceutical compositions comprising said heterocycles and methods of using said heterocycles in the treatment of disease. The heterocycles disclosed herein function as kinase modulators and have utility in the treatment of diseases such as cancer, allergy, asthma, inflammation, obstructive airway disease, autoimmune diseases, metabolic disease, infection, CNS disease, brain tumor, obesity, asthma, hematological disorder, degenerative neural disease, cardiovascular disease, or disease associated with angiogenesis, neovascularization, or vasculogenesis.

  本文提供了取代的吡咯吡啶杂环和取代的吡唑吡啶杂环，以及包含这些杂环的制药组合物和使用这些杂环治疗疾病的方法。本文披露的杂环作为激酶调节剂具有治疗癌症、过敏、哮喘、炎症、阻塞性呼吸道疾病、自身免疫疾病、代谢性疾病、感染、中枢神经系统疾病、脑肿瘤、肥胖症、哮喘、血液疾病、退行性神经疾病、心血管疾病或与血管生成、新生血管形成或血管生成有关的疾病方面的用途。
• Fragment-based discovery of potent inhibitors of the anti-apoptotic MCL-1 protein
  作者：Andrew M. Petros、Steven L. Swann、Danying Song、Kerren Swinger、Chang Park、Haichao Zhang、Michael D. Wendt、Aaron R. Kunzer、Andrew J. Souers、Chaohong Sun

  DOI：10.1016/j.bmcl.2014.02.010

  日期：2014.3

  Apoptosis is regulated by the BCL-2 family of proteins, which is comprised of both pro-death and pro-survival members. Evasion of apoptosis is a hallmark of malignant cells. One way in which cancer cells achieve this evasion is thru overexpression of the pro-survival members of the BCL-2 family. Overexpression of MCL-1, a pro-survival protein, has been shown to be a resistance factor for Navitoclax, a potent inhibitor of BCL-2 and BCL-XL. Here we describe the use of fragment screening methods and structural biology to drive the discovery of novel MCL-1 inhibitors from two distinct structural classes. Specifically, cores derived from a biphenyl sulfonamide and salicylic acid were uncovered in an NMR-based fragment screen and elaborated using high throughput analog synthesis. This culminated in the discovery of selective and potent inhibitors of MCL-1 that may serve as promising leads for medicinal chemistry optimization efforts.
• Triazolopyridines as Selective JAK1 Inhibitors: From Hit Identification to GLPG0634
  作者：Christel J. Menet、Stephen R Fletcher、Guy Van Lommen、Raphael Geney、Javier Blanc、Koen Smits、Nolwenn Jouannigot、Pierre Deprez、Ellen M. van der Aar、Philippe Clement-Lacroix、Liên Lepescheux、René Galien、Béatrice Vayssiere、Luc Nelles、Thierry Christophe、Reginald Brys、Muriel Uhring、Fabrice Ciesielski、Luc Van Rompaey

  DOI：10.1021/jm501262q

  日期：2014.11.26

  Janus kinases (JAK1, JAK2, JAK3, and TYK2) are involved in the signaling of multiple cytokines important in cellular function. Blockade of the JAK-STAT pathway with a small molecule has been shown to provide therapeutic immunomodulation. Having identified JAK1 as a possible new target for arthritis at Galapagos, the compound library was screened against JAK1, resulting in the identification of a triazolopyridine-based series of inhibitors represented by 3. Optimization within this chemical series led to identification of GLPG0634 (65, filgotinib), a selective JAK1 inhibitor currently in phase 2B development for RA and phase 2A development for Crohns disease (CD).
• 1,2,4-Triazolsulfone: A novel isosteric replacement of acylsulfonamides in the context of Na V 1.7 inhibition
  作者：Alessandro A. Boezio、Kristin Andrews、Christiane Boezio、Margaret Chu-Moyer、Katrina W. Copeland、Erin F. DiMauro、Robert S. Foti、Robert T. Fremeau、Hua Gao、Stephanie Geuns-Meyer、Russell F. Graceffa、Hakan Gunaydin、Hongbing Huang、Daniel S. La、Joseph Ligutti、Bryan D. Moyer、Emily A. Peterson、Violeta Yu、Matthew M. Weiss

  DOI：10.1016/j.bmcl.2018.04.035

  日期：2018.6

  Recently, the identification of several classes of aryl sulfonamides and acyl sulfonamides that potently inhibit Na(v)1.7 and demonstrate high levels of selectivity over other Na-v isoforms have been reported. The fully ionizable nature of these inhibitors has been shown to be an important part of the pharmacophore for the observed potency and isoform selectivity. The requirement of this functionality, however, has presented challenges associated with optimization toward inhibitors with drug-like properties and minimal off-target activity. In an effort to obviate these challenges, we set out to develop an orally bioavailable, selective Na(v)1.7 inhibitor, lacking these acidic functional groups. Herein, we report the discovery of a novel series of inhibitors wherein a triazolesulfone has been designed to serve as a bioisostere for the acyl sulfonamide. This work culminated in the delivery of a potent series of inhibitors which demonstrated good levels of selectivity over Na v 1.5 and favorable pharmacokinetics in rodents. (C) 2018 Elsevier Ltd. All rights reserved.