3-羟基苯乙酸甲酯 | 42058-59-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-羟基苯乙酸甲酯
• 中文别名: 2-(3-羟基苯基)乙酸甲酯
• 英文名称: 3-hydroxy-benzeneacetic acid, methyl ester
• 英文别名: methyl (3-hydroxyphenyl)acetate；methyl 2-(3-hydroxyphenyl)acetate
• CAS: 42058-59-3
• 化学式: C₉H₁₀O₃
• mdl: MFCD00017660
• 分子量: 166.177
• InChiKey: AMDDOQIUPAINLH-UHFFFAOYSA-N

物化性质

• 沸点：
  146°C/14mmHg(lit.)
• 密度：
  1.181±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 保留指数：
  1449

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918290000
• 危险性防范说明：
  P273
• 危险性描述：
  H302,H412
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Hydroxyphenylacetic acid methyl ester
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H412: Harmful to aquatic life with long lasting effects
P273: Avoid release to the environment

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Hydroxyphenylacetic acid methyl ester
CAS number: 42058-59-3

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H10O3
Molecular weight: 166.2

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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

反应信息

• 作为反应物：
  描述：

  3-羟基苯乙酸甲酯 在 sodium hydroxide 、 caesium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 43.0h， 生成 2-[3-(喹啉-2-基甲氧基)苯基]乙酸
  参考文献：
  名称：

  N-[（芳基甲氧基）苯基]羧酸，异羟肟酸，四唑和磺酰甲酰胺。新型结构的有效口服活性白三烯D4拮抗剂。

  摘要：

  制备了四个系列的N-[（芳基甲氧基）苯基]化合物作为白三烯D4（LTD4）拮抗剂。在异羟肟酸系列中，3-（2-喹啉基甲氧基）苯乙氧基异羟肟酸甲酯（Wy-48,422，20）是LTD4诱导的支气管收缩的最有效抑制剂，口服ED50为7.9 mg / kg。化合物20还以3.6mg / kg的ED 50口服抑制豚鼠卵白蛋白诱导的支气管收缩。在体外，用吲哚美辛和1-半胱氨酸预处理的LTD4诱导的豚鼠气管收缩，20产生的pKB值为6.08。在磺酰基羧酰胺系列中，N-[（（4-甲基苯基）磺酰基] -3-（2-喹啉基甲氧基）-苯甲酰胺（Wy-49,353，30）是最有效的拮抗剂。化合物30口服抑制LTD4-和卵清蛋白诱导的支气管收缩，ED50分别为0.4和20.2 mg / kg。体外，针对LTD4诱导的豚鼠气管收缩，30产生的pKB值为7.78。在用作上述两个系列中间体的羧酸系列中，3-（2-喹啉基甲氧基）苯乙酸（Wy-46

  DOI：

  10.1021/jm00163a039
• 作为产物：
  描述：

  3-羟基苯乙酸 在 氯化亚砜 作用下， 以 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， 以94%的产率得到3-羟基苯乙酸甲酯
  参考文献：
  名称：

  3-indolyl-4-phenyl-1H-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta

  摘要：

  这项发明涉及抑制糖原合成酶激酶-3β的方法，用于治疗由Th2细胞因子过多引起的疾病，以及3-吲哚基-4-苯基-1H-吡咯-2,5-二酮衍生物的化合物(I)的方法：这些化合物是糖原合成酶激酶-3β的抑制剂，包含它们的药物组合物，使用它们的方法以及制备这些化合物的方法。

  公开号：

  US20020052397A1
• 作为试剂：
  描述：

  3-羟基苯乙酸甲酯 、 (R)-1-(4-甲基苯磺酸酯基)-1,3-丁二醇 在 3-羟基苯乙酸甲酯 作用下， 生成 methyl (R)-2-(3-(3-hydroxybutoxy)phenyl)acetate
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2009, 19, 5617-5621

  摘要：

  DOI：

文献信息

• [EN] COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF BROMODOMAIN-CONTAINING PROTEINS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LA DÉGRADATION CIBLÉE DE PROTÉINES CONTENANT UN BROMODOMAINE
  申请人：ARVINAS INC

  公开号：WO2017030814A1

  公开（公告）日：2017-02-23

  The present invention relates to bifunctional compounds, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the present invention is directed to compounds, which contain on one end a VHL ligand which binds to the ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. The present invention exhibits a broad range of pharmacological activities associated with compounds according to the present invention, consistent with the degradation/inhibition of targeted polypeptides.

  本发明涉及双功能化合物，其作为靶向泛素化的调节剂具有实用性，特别是根据本发明抑制各种多肽和其他蛋白质的化合物。具体而言，本发明涉及一端含有结合泛素连接酶的VHL配体，另一端含有结合靶蛋白的基团的化合物，使得靶蛋白靠近泛素连接酶以促使该蛋白的降解（和抑制）。根据本发明的化合物表现出与靶向多肽的降解/抑制一致的广泛的药理活性。
• Development of [¹⁸F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging
  作者：Kongzhen Hu、Debasis Patnaik、Thomas Lee Collier、Katarzyna N. Lee、Han Gao、Matthew R. Swoyer、Benjamin H. Rotstein、Hema S. Krishnan、Steven H. Liang、Jin Wang、Zhiqiang Yan、Jacob M. Hooker、Neil Vasdev、Stephen J. Haggarty、Ming-Yu Ngai

  DOI：10.1021/acsmedchemlett.6b00405

  日期：2017.3.9

  radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme's aberrant activity. Herein, we report the synthesis and biological evaluation of a series

  糖原合酶激酶3β（GSK-3β）的失调与神经退行性和精神病性疾病的发病机制有关。因此，开发用于正电子发射断层摄影（PET）成像的GSK-3β放射性示踪剂至关重要，因为这种无创成像技术可以更好地了解GSK-3β活性与活生物体中枢神经系统疾病之间的联系，从而可以及早发现该酶的异常活性。在此，我们报告了一系列高亲和力GSK-3β抑制剂氟取代的马来酰亚胺衍生物的合成和生物学评估。实现了潜在的GSK-3β示踪剂[18F] 10a的放射性合成。在啮齿动物中进行的体内PET初步成像研究显示，大脑摄取中等，尽管在大脑中未观察到饱和结合。有必要进一步完善铅支架，以开发用于中枢神经系统PET成像的[18F]标记的GSK-3放射性示踪剂。
• Pharmaceutical compounds
  申请人：Burroughs Wellcome Co.

  公开号：US05405851A1

  公开（公告）日：1995-04-11

  The present invention relates to novel benzoquinazoline thymidylate synthase inhibitors, to pharmaceutical formulations containing them and to their use in medicine.

  本发明涉及新型苯并喹唑嘧啶酸甲脱氧胸苷合成酶抑制剂，以及含有它们的药物配方和它们在医学上的应用。
• Visible Light-Induced Borylation of C–O, C–N, and C–X Bonds
  作者：Shengfei Jin、Hang. T. Dang、Graham C. Haug、Ru He、Viet D. Nguyen、Vu T. Nguyen、Hadi D. Arman、Kirk S. Schanze、Oleg V. Larionov

  DOI：10.1021/jacs.9b12519

  日期：2020.1.22

  photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C‒O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reac-tion exhibits excellent functional group

  硼酸是中心重要的功能基序和合成前体。可见光诱导的硼酸化可以提供结构多样化的硼酸盐，但一种广泛有效的光催化硼酸化方法可以影响包括强 C-O 键在内的多种底物的硼化，仍然难以实现。在此，我们报告了一种通用的、无金属的可见光诱导光催化硼化平台，该平台能够对苯酚和苯胺、氯芳烃以及其他卤代芳烃的富电子衍生物进行硼化。该反应表现出优异的官能团耐受性，正如一系列结构复杂底物的硼化反应所证明的那样。值得注意的是，该反应是由吩噻嗪催化的，这是一种简单的有机光催化剂，MW< 200通过质子耦合电子转移机制介导了以前无法实现的可见光诱导的苯酚衍生物单电子还原，还原电位为~-3 V vs SCE。机理研究指出了光催化剂-碱相互作用的关键作用。
• [EN] INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DE NOROVIRUS ET DE CORONAVIRUS
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2021206876A1

  公开（公告）日：2021-10-14

  Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

  公式（I）化合物及抑制生物样本或患者中病毒复制、减少生物样本或患者中病毒数量、以及治疗患者病毒感染的方法，包括向所述生物样本或患者投与由公式（I）表示的化合物、表A或B中的化合物或其药用可接受盐的有效量。

表征谱图