6-(4-氯苯基)-2-氧代-1,2-二氢-3-吡啶羧酸 | 26118-57-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 6-(4-氯苯基)-2-氧代-1,2-二氢-3-吡啶羧酸
• 英文名称: p-propoxyphenylacetic acid
• 英文别名: 2-(4-(n-propoxy)phenyl)acetic acid；4-propoxyphenylacetic acid；(4-Propoxy-phenyl)-essigsaeure；p-Propyloxyphenylessigsaeure；(4-Propyloxy-phenyl)-essigsaeure；2-(4-propoxyphenyl)acetic acid；p-n-Propoxyphenylessigsaeure；(4-Propoxy-phenyl)-acetic acid
• CAS: 26118-57-0
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD00460580
• 分子量: 194.23
• InChiKey: ULLCOWORODEDBK-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84 °C
• 沸点：
  331.6±17.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2918990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (4-Propoxy-phenyl)-acetic 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: (4-Propoxy-phenyl)-acetic acid
CAS number: 26118-57-0

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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.
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: C11H14O3
Molecular weight: 194.2

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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：

  6-(4-氯苯基)-2-氧代-1,2-二氢-3-吡啶羧酸 在 copper(l) iodide 、 palladium 10% on activated carbon 氯化亚砜 、 亚硝酸特丁酯 、 氢气 、 1,2-二氨基环己烷 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 115.0 ℃ 、517.12 kPa 条件下， 反应 2.0h， 生成 3-(1H-benzo[d]imidazol-6-yl)-4,5-bis(4-propoxyphenyl)oxazolidin-2-one
  参考文献：
  名称：

  NOVEL INHIBITORS

  摘要：

  本发明涉及新颖的吡咯烷衍生物，其具有如下公式(I)：其中R1、R2和R3如本文所述定义，作为谷氨酰胺环化酶（QC，EC 2.3.2.5）的抑制剂。谷氨酰胺环化酶催化N末端谷氨酰胺残基形成焦谷氨酸（5-氧代脯氨酸，pGlu*）的分子内环化，并释放氨，以及催化N末端谷氨酸残基形成焦谷氨酸的分子内环化，并释放水。

  公开号：

  US20110092501A1
• 作为产物：
  描述：

  1-(4-丙氧基-苯基)-乙酮 在 吗啉 、 对甲苯磺酸 、 sulfur 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以40.9%的产率得到6-(4-氯苯基)-2-氧代-1,2-二氢-3-吡啶羧酸
  参考文献：
  名称：

  NOVEL INHIBITORS

  摘要：

  本发明涉及新颖的吡咯烷衍生物，其具有如下公式(I)：其中R1、R2和R3如本文所述定义，作为谷氨酰胺环化酶（QC，EC 2.3.2.5）的抑制剂。谷氨酰胺环化酶催化N末端谷氨酰胺残基形成焦谷氨酸（5-氧代脯氨酸，pGlu*）的分子内环化，并释放氨，以及催化N末端谷氨酸残基形成焦谷氨酸的分子内环化，并释放水。

  公开号：

  US20110092501A1

文献信息

• Structural Modifications of the Quinolin-4-yloxy Core to Obtain New Staphylococcus aureus NorA Inhibitors
  作者：Rolando Cannalire、Gianmarco Mangiaterra、Tommaso Felicetti、Andrea Astolfi、Nicholas Cedraro、Serena Massari、Giuseppe Manfroni、Oriana Tabarrini、Salvatore Vaiasicca、Maria Letizia Barreca、Violetta Cecchetti、Francesca Biavasco、Stefano Sabatini

  DOI：10.3390/ijms21197037

  日期：——

  Efflux pump inhibitors (EPIs) are molecules devoid of any antimicrobial activity, but synergizing with pumps-substrate antibiotics. Herein, we performed an in silico scaffold hopping approach starting from quinolin-4-yloxy-based Staphylococcus aureus NorA EPIs by using previously built pharmacophore models for NorA inhibition activity. Four scaffolds were identified, synthesized, and modified with appropriate

  解决抗菌素耐药性（AMR）代表着一种社会责任，旨在更新抗菌素武器库并确定新颖的治疗方法。在可能的策略中，外排泵抑制作用提供了一个优势，可以对比对所有可挤出药物的耐药性。外排泵抑制剂（EPI）是没有任何抗菌活性但与泵底物抗生素协同作用的分子。在本文中，我们使用先前建立的NorA抑制活性药效基团模型，从基于喹啉4-基氧基的金黄色葡萄球菌NorA EPIs进行了计算机支架跳跃方法。鉴定，合成并用适当的取代基修饰了四个支架，以获得新的化合物，对它们的抗NorA抑制能力以及与氟喹诺酮环丙沙星协同抗金黄色葡萄球菌菌株的能力进行了评估。两种喹啉-4-甲酰胺衍生物3a和3b与环丙沙星的协同作用（MIC降低4倍）显示最佳结果，分别低至3.13和1.56 µg / mL，对人THP-1和A549无毒细胞。通过SA-1199B溴化乙锭外排和针对同基因对SA-K2378（norA ++）/ SA-K1902（no
• PROCESS FOR SYNTHESIZING PHENYLACETIC ACID BY CARBONYLATION OF TOLUENE
  申请人：Physics, Chinese Academy of Sciences Lanzhou Institute of Chemical

  公开号：US20130303798A1

  公开（公告）日：2013-11-14

  A production process for substituted phenylacetic acids or ester analogues thereof is disclosed. In this process toluene or toluene substituted with various substituents, an alcohol, an oxidant and carbon monoxide are used as raw materials to obtain compounds comprising structure of phenylacetic acid ester or analogues thereof by catalysis of the complex catalyst formed from transition metal and ligand, and such compounds are hydrolyzed to obtain various substituted phenylacetic acid based compounds. This type of compounds and their derivatives serve as important fine chemicals used widely in the industries of pharmaceuticals, pesticides, perfume and the like.

  揭示了一种用于取代苯乙酸或其酯类似物的生产工艺。在这个工艺中，甲苯或带有各种取代基的甲苯、醇、氧化剂和一氧化碳被用作原料，通过过渡金属和配体形成的复合催化剂的催化作用，获得包含苯乙酸酯结构或其类似物的化合物，并且这些化合物被水解以获得各种基于取代苯乙酸的化合物。这类化合物及其衍生物在制药、农药、香水等行业中被广泛应用，作为重要的精细化学品。
• Fragment-Based Structural Optimization of a Natural Product Itampolin A as a p38α Inhibitor for Lung Cancer
  作者：Jing-wei Liang、Ming-yang Wang、Shan Wang、Xin-yang Li、Fan-hao Meng

  DOI：10.3390/md17010053

  日期：——

  Marine animals and plants provide abundant secondary metabolites with antitumor activity. Itampolin A is a brominated natural tyrosine secondary metabolite that is isolated from the sponge Iotrochota purpurea. Recently, we have achieved the first total synthesis of this brominated tyrosine secondary metabolite, which was found to be a potent p38α inhibitor exhibiting anticancer effects. A fragment-based

  海洋动植物提供具有抗肿瘤活性的丰富的次生代谢产物。Itampolin A是一种溴化的天然酪氨酸次级代谢产物，它是从海绵紫罗兰（Iotrochota purpurea）分离得到的。最近，我们已经完成了该溴化酪氨酸次级代谢产物的第一个全合成反应，发现这是一种有效的p38α抑制剂，具有抗癌作用。进行了基于片段的药物设计（FBDD），以优化ItampolinA。合成了45种溴化酪氨酸衍生物，具有有趣的生物学活性。然后，进行了QSAR研究，以探讨负责溴化酪氨酸骨架p38α抑制剂活性的结构决定因素。铅化合物通过FBDD方法进行了优化，然后合成了三个系列的溴化酪氨酸衍生物，并评估了它们对p38α和肿瘤细胞的抑制活性。化合物6o（IC50 = 0.66μM）对非小细胞肺A549细胞（A549）表现出显着的抗肿瘤活性。这也证明了FBDD结构优化方法的可行性。
• Synthesis of some new benzimidazole-5(6)-carboxylic acids
  作者：Hakan Göker、Süreyya Ölgen、Rahmiye Ertand、HÜLya Akgün、Süheyla Özbey、Engin Kendi、GÜL Topçu

  DOI：10.1002/jhet.5570320617

  日期：1995.11

  The title compounds, 1,2-dialkyl-benzimidazole-5(6)-carboxylic acids 34–45 were prepared at four steps; 1) preparation of mono amide derivatives 1–11 by the reaction of methyl 3,4-diaminobenzoate and substituted phenyl or phenoxyacetic acid chlorides; 2) preparation of the methyl benzimidazolecarboxyl-ates 12–22, with zinc chloride and dry hydrogen chloride gas; 3) alkaline hydrolysis of the esters

  标题化合物1,2-二烷基苯并咪唑-5（6）-羧酸34-45的制备分为四个步骤；1）通过3,4-二氨基苯甲酸甲酯与取代的苯基或苯氧乙酸氯的反应制备单酰胺衍生物1-11；2）用氯化锌和干燥的氯化氢气体制备苯并咪唑甲酸甲酯12-22。3）酯23-33的碱水解；4）在碱性介质中用苄基或对氟苄基溴取代咪唑环。2-芳基苯并咪唑-5-（6） -羧酸50-53制备通过 3,4-二氨基苯甲酸和芳香醛与铜离子的氧化缩合反应
• Synthesis and microbiological activity of some novel 5-benzamido- and 5-phenylacetamido- substituted 2-phenylbenzoxazole derivatives
  作者：Esin Akı Şener、Özlem Temiz Arpacı、İsmail Yalçın、Nurten Altanlar

  DOI：10.1016/s0014-827x(00)00059-8

  日期：2000.5

  The synthesis and microbiological activity of a new series of 5-benzamido- and 5-phenylacetamidosubstituted-2-phenylbenzoxazole derivatives (1-26) were described. The in vitro microbiological activity of the compounds was determined against Gram-positive, Gram-negative bacteria and the yeast Candida albicans in comparison with standard drugs. Microbiological results indicated that the synthesized compounds

  描述了一系列新的5-苯甲酰胺基和5-苯基乙酰氨基取代的-2-苯基苯并恶唑衍生物（1-26）的合成和微生物活性。与标准药物相比，测定了该化合物对革兰氏阳性，革兰氏阴性细菌和白色念珠菌的体外微生物活性。微生物学结果表明，合成的化合物对被测微生物具有广泛的活性。化合物1、21、25显示出比四环素和链霉素更高的抗铜绿假单胞菌的活性。