(4-乙氧羰基甲苯基)硼酸片钠醇酯 | 859169-20-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 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: (4-乙氧羰基甲苯基)硼酸片钠醇酯
• 英文名称: ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
• 英文别名: ethyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
• CAS: 859169-20-3
• 化学式: C₁₆H₂₃BO₄
• 分子量: 290.167
• InChiKey: RPRBNRDIESZHFL-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Ethoxycarbonylmethylphenylboronic acid, pinacol ester
Synonyms: (4-Ethoxycarbonylmethyl)phenylboronic acid, pinacol ester

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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: 4-Ethoxycarbonylmethylphenylboronic acid, pinacol ester
CAS number: 859169-20-3

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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, 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: C16H23BO4
Molecular weight: 290.2

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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.

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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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-(羧基甲基)苯硼酸频那醇酯	2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid	797755-07-8	C14H19BO4	262.113
  4-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)氯苯	4-chlorophenylboronic acid pinacol ester	195062-61-4	C12H16BClO2	238.522

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-(羧基甲基)苯硼酸频那醇酯	2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid	797755-07-8	C14H19BO4	262.113
  ——	[4'-(4,4,5,5-tetramethyl-[1,3,2]di-oxaborolan-2-yl)-biphenyl-4-yl]-acetic acid ethyl ester	1396007-84-3	C22H27BO4	366.265
  4-乙氧基羰基甲基苯硼酸	[4-(2-ethoxy-2-oxoethyl)phenyl]boronic acid	92243-74-8	C10H13BO4	208.022

反应信息

• 作为反应物：
  描述：

  (4-乙氧羰基甲苯基)硼酸片钠醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 lithium hydroxide monohydrate 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 27.0h， 生成 2-(3'-(5-(3-(3,5-dichloropyridin-4-yl)ureido)-1-ethyl-6-oxo-1,6-dihydropyridazin-3-yl)-[1,1'-biphenyl]-4-yl)acetic acid
  参考文献：
  名称：

  Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure–Activity Relationships

  摘要：

  Cyclic nucleotide cAMP is a ubiquitous secondary messenger involved in a plethora of cellular responses to biological agents involving activation of adenylyl cyclase. Its intracellular levels are tightly controlled by a family of cyclic nucleotide degrading enzymes, the PDEs. In recent years, cyclic nucleotide phosphodiesterase type 4 (PDE4) has aroused scientific attention as a suitable target for anti-inflammatory therapy in respiratory diseases, particularly in the management of asthma and COPD. Here we describe our efforts to discover novel, highly potent inhaled inhibitors of PDE4. Through structure based design, with the inclusion of a variety of functional groups and physicochemical profiles in order to occupy the solvent filled pocket of the PDE4 enzyme, we modified the structure of our oral PDE4 inhibitors to reach compounds down to picomolar enzymatic potencies while at the same time tackling successfully an uncovered selectivity issue with the adenosine receptors. In vitro potencies were demonstrated in a rat lung neutrophilia model by administration of a suspension with a Penn-Century Micro Sprayer Aerosolizer.

  DOI：

  10.1021/acs.jmedchem.6b00829
• 作为产物：
  描述：

  对溴苯乙酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 氯化亚砜 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 (4-乙氧羰基甲苯基)硼酸片钠醇酯
  参考文献：
  名称：

  COFERONS AND METHODS OF MAKING AND USING THEM

  摘要：

  本发明涉及一种用于制备治疗性化合物的单体。该单体包括一个或多个可与目标分子结合的药效团，其解离常数小于300微摩尔，以及与药效团连接的连接元素。所述连接元素的分子量小于500道尔顿，通过直接连接或通过连接器间接与药效团相连。

  公开号：

  US20120295874A1

文献信息

• NOVEL TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160176864A1

  公开（公告）日：2016-06-23

  The present invention is directed to tricyclic compounds, pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物，包括本发明化合物的药用可接受组合物以及在治疗各种疾病中使用所述组合物的方法。
• [EN] TRICYCLIC COMPOUNDS AS ANTICANCER AGENTS<br/>[FR] COMPOSÉS TRICYCLIQUES COMME AGENTS ANTI-CANCERS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015100282A1

  公开（公告）日：2015-07-02

  The present invention is directed to tricyclic compounds (I), pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

  本发明涉及三环化合物（I），包括本发明化合物的药用可接受组合物以及使用所述组合物治疗各种疾病的方法。
• Pyrazoloadenine Inhibitors of the RET Lung Cancer Oncoprotein Discovered by a Fragment Optimization Approach
  作者：Debasmita Saha、Katie Rose Ryan、Naga Rajiv Lakkaniga、Erica Lane Smith、Brendan Frett

  DOI：10.1002/cmdc.202100013

  日期：2021.5.18

  A fragment-based drug-discovery approach was used on a pyrazoloadenine fragment library to uncover new molecules that target the RET (REarranged during Transfection) oncoprotein, which is a driver oncoprotein in ∼2 % of non-small-cell lung cancers. The fragment library was screened against the RET kinase and LC-2/ad (RET-driven), KM-12 (TRKA-driven matched control) and A549 (cytotoxic control) cells

  基于片段的药物发现方法用于吡唑核苷片段库，以发现靶向 RET（转染期间重新排列）癌蛋白的新分子，该蛋白是约 2% 的非小细胞肺癌的驱动癌蛋白。针对 RET 激酶和 LC-2/ad（RET 驱动）、KM-12（TRKA 驱动匹配对照）和 A549（细胞毒性对照）细胞筛选片段文库，以鉴定可抑制 RET 驱动生长的选择性支架。在生化测定中发现未取代的吡唑核苷片段对 RET 有活性，但降低了非 RET 驱动的细胞系中的细胞活力 (EC 50= 1 和 3 μM，分别）。为了提高 RET 的选择性，在 RET 活性位点中模拟了吡唑核苷，并确定了两个结构域，用吡唑核苷片段衍生物进行探测以提高 RET 亲和力。合并每个结构域的支架以生成新型先导化合物8 p，它对 RET 癌蛋白表现出更高的活性和选择性（A549 EC 50 =5.92 μM，LC-2/ad EC 50 =0.016 μM，RET IC 50
• Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide‐Functionalized Phosphine Ligands
  作者：Zhiyong Hu、Xiao‐Jing Wei、Jens Handelmann、Ann‐Katrin Seitz、Ilja Rodstein、Viktoria H. Gessner、Lukas J. Gooßen

  DOI：10.1002/anie.202016048

  日期：2021.3.15

  organozinc reagents with aryl electrophiles using a cyclohexyl‐YPhos ligand bearing an ortho‐tolyl‐substituent in the backbone. This highly electron‐rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively

  芳基氯化物与Reformatsky试剂的偶联是构建α-芳基酯的理想策略，但由于各种可能的副反应带来许多挑战，到目前为止，在基质范围上已受到很大的限制。现在，通过调整内酯官能化的膦以满足Negishi联轴器的要求，克服了这一局限性。使用在主链上带有邻甲苯基取代基的环己基-YPhos配体，在钯催化的有机锌试剂与芳基亲电试剂的芳基化中达到了创纪录的活性。这种高度电子富集的庞大配体使得可以在Reformatsky试剂的室温偶联中使用芳基氯化物。反应范围包括各种官能化的芳酸和芳基丙酸衍生物。
• [EN] N-ARYLTRIAZOLE COMPOUNDS AS LPAR ANTAGONISTS<br/>[FR] COMPOSÉS N-ARYLTRIAZOLE UTILISÉS COMME ANTAGONISTES DE LPAR
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013189865A1

  公开（公告）日：2013-12-27

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, pulmonary fibrosis.

  提供以下公式(I)的化合物：以及 pharmaceutically 可接受的盐，其中取代基如说明书所述。这些化合物以及包含它们的药物组合物可用于治疗炎症性疾病和障碍，例如，例如，肺纤维化。