2-羟基-[1,1-联苯]-3-羧酸甲酯 | 92254-28-9

• 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-羟基-[1,1-联苯]-3-羧酸甲酯
• 英文名称: methyl 2'-hydroxybiphenyl-3-carboxylate
• 英文别名: methyl 3-(2-hydroxyphenyl)benzoate；2-Hydroxy-biphenyl-carbonsaeure-(3')-methylester；Methyl 2'-hydroxy-[1,1'-biphenyl]-3-carboxylate
• CAS: 92254-28-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: BRGRVHYFRYIRLD-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  380.0±25.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(3-Methoxycarbonylphenyl)phenol
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-(3-Methoxycarbonylphenyl)phenol
CAS number: 92254-28-9

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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.
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: C14H12O3
Molecular weight: 228.2

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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：

  2-羟基-[1,1-联苯]-3-羧酸甲酯 在 lithium hydroxide 、 N-羟基丁二酰亚胺 、 三氟化硼乙醚 、 对甲苯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 丙酮 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.75h， 生成 ethyl 2-[[3-[2-[[(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]oxy]phenyl]benzoyl]amino]acetate
  参考文献：
  名称：

  Rational Design and Synthesis of Small Molecule, Non-oligosaccharide Selectin Inhibitors: (.alpha.-D-Mannopyranosyloxy)biphenyl-Substituted Carboxylic Acids

  摘要：

  The calcium dependent E-selectin/sialyl Lewis(x) (sLe(x)) interaction plays a key role in inflammation where it mediates the rolling of leukocytes prior to firm adhesion and extravasation from the vasculature. A model of E-selectin/sLe(x) binding, along with previously reported structure-activity relationships of sLe(x)-related oligosaccharide, was used in the rational design of non-oligosaccharide inhibitors of this pivotal interaction. A palladium-mediated biaryl-coupling (Suzuki) reaction was used as the key step to prepare a number of substituted biphenyls which were assayed for their ability to inhibit the binding of E-, P-, and L-selectin-IgG fusion proteins to sLe(x) expressed on the surface of HL60 cells. Some of the compounds developed had greater in vitro potency than the parent sLe(x) tetrasaccharide and are currently being evaluated in in vivo models of inflammation to select a candidate for clinical development.

  DOI：

  10.1021/jm00026a004
• 作为产物：
  描述：

  2'-甲氧基联苯-3-羧酸甲酯 以 甲醇 、 ice-water 、 二氯甲烷 为溶剂， 以0.95 g (84%)的产率得到2-羟基-[1,1-联苯]-3-羧酸甲酯
  参考文献：
  名称：

  Compositions and methods of inhibiting the binding of E-selectin or

  摘要：

  本发明涉及抑制E-选择素或P-选择素与细胞表面上呈现的唾液酸基-刘易斯X或唾液酸基-刘易斯A结合的化合物，其具有以下一般结构：##STR1## 本发明还涉及使用所述化合物抑制E-选择素或P-选择素与细胞表面上呈现的唾液酸基-刘易斯X或唾液酸基-刘易斯A结合的方法，以及包含抑制E-选择素与唾液酸基-刘易斯X结合的化合物的药用活性组合物，以及治疗败血症休克、ARDS、克罗恩病、牛皮癣和类风湿性关节炎等慢性炎症性疾病以及心脏病发作、中风和器官移植后发生的再灌注损伤及癌症的治疗方法。

  公开号：

  US05622937A1

文献信息

• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：POLYPHOR AG

  公开号：US20150051183A1

  公开（公告）日：2015-02-19

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义的大环环系统由三个不同的分子部分组成：模板A、构象调节剂B和桥C。由这种环系统I描述的大环可通过并行合成或溶液中或固相上的组合化学轻松制造。它们被设计用于与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，酶的抑制活性或抗菌活性。特别是，这些大环显示对亚型1的内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶卡特普辛S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃素3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Structure-based discovery of glycomimetic FmlH ligands as inhibitors of bacterial adhesion during urinary tract infection
  作者：Vasilios Kalas、Michael E. Hibbing、Amarendar Reddy Maddirala、Ryan Chugani、Jerome S. Pinkner、Laurel K. Mydock-McGrane、Matt S. Conover、James W. Janetka、Scott J. Hultgren

  DOI：10.1073/pnas.1720140115

  日期：2018.3.20

  of ∼90 nM, representing a major advancement in potency relative to the characteristically weak nature of most carbohydrate–lectin interactions. 29β-NAc binds tightly to FmlH by engaging the residues Y46 through edge-to-face π-stacking with its A-phenyl ring, R142 in a salt-bridge interaction with its carboxylate group, and K132 through water-mediated hydrogen bonding with its N-acetyl group. Administration

  由于在全球范围内传播多药抗生素耐药性，细菌感染的治疗正成为一项严重的临床挑战，因此有必要寻找替代疗法来消除这些感染的致病机制。泌尿道致病性大肠杆菌（UPEC）使用多种分子伴侣-胶合剂通路菌毛，其中的黏附素具有不同的受体特异性，可以在各种宿主组织和生境中定殖。例如，UPEC F9菌毛特异性结合在肾脏和发炎的膀胱上的半乳糖或N-乙酰半乳糖胺表位。使用X射线结构指导方法，虚拟筛选和多重ELISA阵列，我们合理设计了芳基半乳糖苷和N抑制F9菌毛粘附素FmlH的-乙酰半乳糖氨基糖苷。铅化合物29β-NAc是具有K i的联苯基N-乙酰基-β-半乳糖氨基糖苷大约90 nM，相对于大多数碳水化合物-凝集素相互作用的特征较弱的特性，其效能有了很大的提高。29β-NAc通过与A46环通过面对面π堆叠与残基Y46，与羧酸酯基团进行盐桥相互作用的R142和与水通过氢键结合的K132与残基Y46紧密结合，从而与FmlH紧密结合。
• Conformationally constrained, fully synthetic macrocyclic compounds
  申请人：POLYPHOR AG

  公开号：US10017481B2

  公开（公告）日：2018-07-10

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  式（I）的构象受限、空间限定的大环环系统由三个不同的分子部分构成，分别是模板 A、构象调节剂 B 和桥 C：这种环系统 I 所描述的大环很容易通过平行合成或组合化学在溶液或固相中制造出来。它们可与各种特定的生物靶标相互作用，例如对 G 蛋白偶联受体（GPCR）的激动或拮抗活性、对酶的抑制活性或抗菌活性。特别是，这些大环化合物对亚型 1 内皮素转换酶（ECE-1）和/或半胱氨酸蛋白酶 cathepsin S（CatS）具有抑制活性，和/或可作为催产素（OT）受体的拮抗剂、或白三烯 B4（LTB4）受体的拮抗剂，和/或作为弹力素 3（BB3）受体的激动剂，和/或对至少一种细菌菌株具有抗菌活性。因此，它们作为治疗各种疾病的药物显示出巨大的潜力。
• BINDING OF E-SELECTIN, P-SELECTIN OR L-SELECTIN TO SIALYL-LEWISx OR SIALYL-LEWISa
  申请人：TEXAS BIOTECHNOLOGY CORPORATION

  公开号：EP0758243A1

  公开（公告）日：1997-02-19