3-(4-羟基-3-硝基苯基)-丙酸 | 38196-09-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(4-羟基-3-硝基苯基)-丙酸
• 中文别名: 3-(4-羟基-3-硝基苯基)丙酸
• 英文名称: 3-(4-hydroxy-3-nitrophenyl)propanoic acid
• 英文别名: 3-(4-hydroxy-3-nitrophenyl)propionic acid；4-hydroxy-3-nitrobenzenepropanoic acid；3-(4-hydroxy-3-nitro-phenyl)-propionic acid；β-(3-Nitro-4-oxy-phenyl)-propionsaeure；3-(4-Hydroxy-3-nitro-phenyl)-propionsaeure；3-Nitro-hydro-p-cumarsaeure
• CAS: 38196-09-7
• 化学式: C₉H₉NO₅
• mdl: MFCD00045947
• 分子量: 211.174
• InChiKey: KPJMKEOLALLMDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  103
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2918290000
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(4-Hydroxy-3-nitrophenyl)propanoic 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: 3-(4-Hydroxy-3-nitrophenyl)propanoic acid
CAS number: 38196-09-7

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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: C9H9NO5
Molecular weight: 211.2

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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, nitrogen oxides.

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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-(4-羟基-3-硝基苯基)-丙酸 在 正丁基锂 、 lithium hydroxide monohydrate 、 platinum(IV) oxide trihydrate 、 偶氮二甲酸二异丙酯 、 硫酸 、 palladium 10% on activated carbon 、 乙基溴化镁 、 potassium tert-butylate 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~150.0 ℃ 、101.33 kPa 条件下， 反应 49.84h， 生成 (S)-methyl 2-(4-chlorophenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives

  摘要：

  Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.028
• 作为产物：
  描述：

  对羟基苯丙酸 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 3-(4-羟基-3-硝基苯基)-丙酸
  参考文献：
  名称：

  新型苯并恶唑衍生物的设计，合成及抗菌性能评价

  摘要：

  描述了（S）-2-（4-叔丁基苯氧基）-3-（苯并恶唑-5-基）丙酸衍生物（2a-k）的合成，并确定了它们对革兰氏阴性和-的体外抗菌活性。阳性细菌。发现这些化合物对所筛选的细菌具有广谱的活性，但发现白色念珠菌真菌的MIC值较差。带有疏水性芳香键的化合物2b是所有细菌中活性最高的衍生物，MIC值为0.098至0.78μg/ mL。2b对枯草芽孢杆菌的活性 比青霉素高2倍，比其他对照抗生素高8至510倍。

  DOI：

  10.1016/j.ejmech.2016.10.010

文献信息

• Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine
  作者：Olesja Koleda、Timo Broese、Jan Noetzel、Michael Roemelt、Edgars Suna、Robert Francke

  DOI：10.1021/acs.joc.7b01686

  日期：2017.11.17

  The indirect (“ex-cell”) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our “ex-cell” approach toward

  据报道，使用基于碘（I）/碘（III）氧化还原对的氧化还原介体从亚胺间接（“细胞外”）电化学合成苯并恶唑。将氧化还原活性的碘代苯基亚基束缚到四烷基铵部分上，从而可以在不支持电解质的情况下进行阳极氧化。介体盐可以很容易地回收和再利用。我们对苯并恶唑进行电合成的“细胞外”方法与一系列对氧化还原敏感的官能团兼容。在控制实验和DFT计算的基础上，提出了前所未有的协同消除苯并恶唑形成的机理。
• Mild Bioconjugation Through the Oxidative Coupling of<i>ortho</i>-Aminophenols and Anilines with Ferricyanide
  作者：Allie C. Obermeyer、John B. Jarman、Chawita Netirojjanakul、Kareem El Muslemany、Matthew B. Francis

  DOI：10.1002/anie.201307386

  日期：2014.1.20

  Using a small‐molecule‐based screen, ferricyanide was identified as a mild and efficient oxidant for the coupling of anilines and o‐aminophenols on protein substrates. This reaction is compatible with thiols and 1,2‐diols, allowing its use in the creation of complex bioconjugates for use in biotechnology and materials applications.

  使用基于小分子的筛查，铁氰化物被鉴定为一种在蛋白质底物上偶联苯胺和邻氨基苯酚的温和而有效的氧化剂。该反应与硫醇和1,2-二醇兼容，可用于创建复杂的生物共轭物，用于生物技术和材料应用。
• Easy Oxidation and Nitration of Human Myoglobin by Nitrite and Hydrogen Peroxide
  作者：Stefania Nicolis、Andrea Pennati、Eleonora Perani、Enrico Monzani、Anna Maria Sanangelantoni、Luigi Casella

  DOI：10.1002/chem.200500361

  日期：2006.1.11

  The modification of human myoglobin (HMb) by reaction with nitrite and hydrogen peroxide has been investigated. This reaction is important because NO(2) (-) and H(2)O(2) are formed in vivo under conditions of oxidative and nitrative stress, where protein derivatization has been often observed. The abundance of HMb in tissues and in the heart makes it a potential source and target of reactive species

  已经研究了通过与亚硝酸盐和过氧化氢反应对人肌红蛋白（HMb）进行修饰的方法。此反应很重要，因为NO（2）（-）和H（2）O（2）是在氧化和硝化应激条件下体内形成的，在该条件下经常观察到蛋白质衍生化。HMb在组织和心脏中的丰度使其成为体内产生的反应物种的潜在来源和目标。HMb / H（2）O（2）/ NO（2）（-）产生的氧化剂和硝化物质是二氧化氮和过氧亚硝酸盐，它们可以与外源底物和内源性蛋白质残基反应。通过化学计算量的H（2）O（2）和NO（2）（-）修饰的HMb的串联质量分析表明存在两种内源性衍生化作用：将C110氧化为亚磺酸（76％）和将Y103硝化为3 -硝基酪氨酸（44％）。当使用更高浓度的NO（2）（-）和H（2）O（2）时，还观察到Y146和血红素的硝化作用。改性HMbs的二维凝胶电泳分析显示，斑点比野生型HMb酸性更高，这与亚磺酸和硝基酪氨酸残基的形成相一致。相比之下，如HM
• Azole derivative with leukotriene (LTs) antagonizing activity and
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US05981559A1

  公开（公告）日：1999-11-09

  An azole derivative represented by general formula (I) or a pharmaceutically acceptable salt thereof, having both of a leukotriene antagonistic effect and a thromboxane A2 antagonistic effect and being useful in preventing or treating allergic diseases, ischemic heart diseases or ischemic brain diseases, and a medicinal composition containing the same as the active ingredient, wherein R.sup.1 and R.sup.2 may be the same or different and represent each hydrogen, cycloalkyl, etc., or R.sup.1 and R.sup.2 together with (a) may form a fused ring (b) or (c) which may be substituted by optionally substituted lower alkyl, amino, etc.; R.sup.3, R.sup.6, R.sup.7, R.sup.8 may be the same or different and represent each hydrogen, amino, etc.; R.sup.4 represents cyano, tetrazolyl, --COOR.sup.9, etc.; R.sup.5 represents hydrogen or lower alkyl; D represents optionally substituted lower alkylene; X and Z may be the same or different and represent each oxygen or sulfur; Y represents --N.dbd. or --CH.dbd.; A represents --O--B--, --B--O--, --S--B--, --B--S-- or --B-- (B being lower alkylene or lower alkenylene); and n is 0, 1, or 2.

  一种由通式（I）表示的唑类衍生物或其药学上可接受的盐，具有白三烯拮抗作用和血栓素A2拮抗作用，可用于预防或治疗过敏性疾病、缺血性心脏病或缺血性脑病，以及含有其作为活性成分的药物组合物，其中R.sup.1和R.sup.2可以相同或不同，分别表示氢、环烷基等，或者R.sup.1和R.sup.2与（a）一起可以形成被可选择地取代的较低烷基、氨基等取代的融合环（b）或（c）；R.sup.3、R.sup.6、R.sup.7、R.sup.8可以相同或不同，分别表示氢、氨基等；R.sup.4表示氰基、四唑基、-COOR.sup.9等；R.sup.5表示氢或较低烷基；D表示可选择地取代的较低亚烷基；X和Z可以相同或不同，分别表示氧或硫；Y表示-N.dbd.或-CH.dbd.；A表示-O--B--，-B--O--，-S--B--，-B--S--或-B--（B为较低烷基或较低烯基）；n为0、1或2。
• Melanin-concentrating hormone antagonist
  申请人：——

  公开号：US20030158177A1

  公开（公告）日：2003-08-21

  A melanin-concentrating hormone antagonist comprising a compound of the formula: 1 wherein R is hydrogen atom or a cyclic group which may be substituted; X is a bond or a spacer having a main chain of 1 to 10 atoms; Y is a spacer having a main chain of 1 to 6 atoms; ring A is benzene ring which may be further substituted; ring B is a 5- to 9-membered nitrogen-containing non-aromatic heterocyclic ring which may be further substituted; R 1 and R 2 are the same or different and are hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; or R 1 and R 2 , together with the adjacent nitrogen atom, may form a nitrogen-containing heterocyclic ring which may be substituted; or R 2 , together with the adjacent nitrogen atom and Y, may form a nitrogen-containing heterocyclic ring which may be substituted; or a salt thereof is useful as a preventive or therapeutic agent for obesity, etc.

  一种黑素浓缩激素拮抗剂，包括以下结构的化合物：其中R是氢原子或可能被取代的环状基团；X是具有1到10个原子主链的键或间隔物；Y是具有1到6个原子主链的间隔物；环A是苯环，可能进一步被取代；环B是一个含氮的非芳香杂环环，成员数为5到9，可能进一步被取代；R1和R2相同或不同，是氢原子、可能被取代的烃基或可能被取代的杂环基；或者R1和R2，与相邻的氮原子一起，可以形成一个可能被取代的含氮杂环环；或者R2，与相邻的氮原子和Y一起，可以形成一个可能被取代的含氮杂环环；或其盐可用作肥胖等疾病的预防或治疗剂。