N-2,4-二硝基苯-L-苯丙氨酸 | 1655-54-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-2,4-二硝基苯-L-苯丙氨酸
• 中文别名: N-(2,4-二硝基苯基)-L-苯丙胺酸；N-2,4-DNP-L-苯丙氨酸
• 英文名称: N(2,4-dinitrophenyl)-(S)-phenylalanine
• 英文别名: N-(2,4-dinitrophenyl)-L-phenylalanine；N-(2,4-dinitrophenyl)-phenylanine；DNP-L-phenylalanine；DNP-phenylalanine；N-(2,4-dinitro-phenyl)-L-phenylalanine；N-(2,4-Dinitro-phenyl)-L-phenylalanin；(2S)-2-(2,4-dinitroanilino)-3-phenylpropanoic acid
• CAS: 1655-54-5
• 化学式: C₁₅H₁₃N₃O₆
• 分子量: 331.285
• InChiKey: HJQHTLAEPSKXQJ-ZDUSSCGKSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  588.5±50.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)
• 溶解度：
  在甲醇中几乎透明

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险等级：
  4.1
• WGK Germany：
  3
• 危险品运输编号：
  UN 1325
• 海关编码：
  2922499990
• 包装等级：
  II
• 危险类别：
  4.1
• 储存条件：
  -20°C密封保存

SDS

N-(2,4-Dinitrophenyl)-L-phenylalanine Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: N-(2,4-Dinitrophenyl)-L-phenylalanine

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 1
Flammable solids
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Hazard statements Flammable solid
Precautionary statements:
[Prevention] Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
Use explosion-proof electrical/ventilating/lighting equipment.
Wear protective gloves/eye protection/face protection.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
N-(2,4-Dinitrophenyl)-L-phenylalanine
Components:
Percent: >98.0%(LC)(T)
CAS Number: 1655-54-5
Synonyms: N-Dnp-L-phenylalanine , Dnp-Phe-OH
Chemical Formula: C15H13N3O6

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
N-(2,4-Dinitrophenyl)-L-phenylalanine
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Explosion risk in case of fire. Fight fire remotely due to the risk of explosion.
from the chemical: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Keep containers cool by
spraying with water. Eliminate all ignition sources if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Be careful not to cause leakage, overflow, or dispersion. Steam should not be
generated unnecessarily. Keep away from heat/sparks/open flame/hot surfaces. -No
smoking. Take measures to prevent the build up of electrostatic charge. Use
explosion-proof equipment. Avoid shock and friction. Wash hands and face before
breaks and immediately after handling the product.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Be sure not to give the container unexpected impacts, such as falling down or falling
off.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: Pale yellow - Yellow
Odour: No data available
N-(2,4-Dinitrophenyl)-L-phenylalanine

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:187°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous May explosively decompose on heating, shock, friction, etc.
reactions:
Conditions to avoid: Heat, Spark, Open flame, Static discharge, Shock, Friction
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities and an expert of disposal. You may be able
to dissolve or mix material with a combustible solvent and little by little burn in a chemical incinerator equipped with
an afterburner and scrubber system. If a large amount of the substance is burned at a time, an explosion may
occur. Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: 4.1: Flammable solid.
UN-No: 1325
N-(2,4-Dinitrophenyl)-L-phenylalanine

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Section 14. TRANSPORT INFORMATION
Proper shipping name: Flammable solid, organic, n.o.s.
Packing group: II

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-(2,4-二硝基苯基)-L-苯丙氨酸是一种以丙氨酸为衍生基础的化合物[1]。

反应信息

• 作为反应物：
  描述：

  N-2,4-二硝基苯-L-苯丙氨酸 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 2-benzyl-5-nitro-1H-benzimidazole 3-oxide
  参考文献：
  名称：

  去质子化的 N-(2,4-二硝基苯基)氨基酸在溶液和气相中发生环化

  摘要：

  N-(2,4-二硝基苯基)丙氨酸和苯丙氨酸 [M-H](-) 的碰撞活化质谱碎片可能是 N-(2,4-二硝基苯基)氨基的碱催化环化的气相类似物二恶烷水溶液中的酸。后一种反应是 2-取代的 5-硝基-1H-苯并咪唑-3-氧化物的来源之一，它们是抗菌剂。通过串联质谱实验建立并由使用 DFT 方法的分子建模支持的两种化合物的碎片表明 [M - H](-) 离子通过 CO(2) 和 H(2)O 的顺序消除而解离以产生去质子化的苯并咪唑-N-氧化物衍生物。气相环化反应类似于溶液中碱催化的环化反应，不同的是在后一种情况下，反应物必须是二价阴离子，反应才能在合理的时间范围内发生。少一个硝基的 N-(2-硝基苯基)苯丙氨酸的环化需要比在 4 位具有第二个硝基的化合物更强的环化碱。随着 CO(2) 和 H(2)O 的流失，中性分子和自由基都会被驱逐，后者是违反偶电子离子规则的例子。

  DOI：

  10.1016/j.ijms.2011.01.007
• 作为产物：
  描述：

  L-苯丙氨酸 、 2,4-二硝基氟苯 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.01h， 以93%的产率得到N-2,4-二硝基苯-L-苯丙氨酸
  参考文献：
  名称：

  聚焦微波辐射下芳基卤化物与氨基酸的高效亲核取代反应

  摘要：

  在微波辐射下，在40 s内完成了2,4-二硝基氟苯与氨基酸的亲核取代反应，收率高达93％，远远优于传统加热条件下的收率。

  DOI：

  10.1016/s0040-4020(00)00739-0

文献信息

• Novel Compounds for the Treatment of Diseases Associated with Amyloid or Amyloid-Like Proteins
  申请人：Kroth Heiko

  公开号：US20110280808A1

  公开（公告）日：2011-11-17

  The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.

  本发明涉及一种新型化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常，如阿尔茨海默病，以及与淀粉样蛋白类似蛋白相关的疾病或病况。本发明的化合物还可用于治疗与视觉系统组织中的病理异常/变化相关的眼部疾病。本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物制备用于治疗或预防与淀粉样和/或淀粉样类似蛋白相关的疾病或病况的药物的用途。还公开了一种治疗或预防与淀粉样和/或淀粉样类似蛋白相关的疾病或病况的方法。
• [EN] NOVEL COMPOUNDS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH AMYLOID OR AMYLOID-LIKE PROTEINS<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT DE MALADIES ASSOCIÉES AUX PROTÉINES AMYLOÏDES OU DE TYPE AMYLOÏDE
  申请人：AC IMMUNE SA

  公开号：WO2011128455A1

  公开（公告）日：2011-10-20

  The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.

  本发明涉及一类新化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常，例如阿尔茨海默病，以及与类淀粉样蛋白相关的疾病或状况。本发明的化合物还可用于治疗与视觉系统组织病理性异常/变化相关的眼病。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物制备用于治疗或预防与淀粉样和/或类淀粉样蛋白相关的疾病或状况的药物。还公开了一种治疗或预防与淀粉样和/或类淀粉样蛋白相关疾病或状况的方法。
• Studies on fungal products. XI Isolation and structures of novel cyclic pentapeptides from Aspergillus sp. NE-45.
  作者：REIJI KOBAYASHI、YUJI SAMEJIMA、SHOICHI NAKAJIMA、KEN-ICHI KAWAI、SHUN-ICHI UDAGAWA

  DOI：10.1248/cpb.35.1347

  日期：——

  Three new compounds designated as cycloaspeptides A (1), B (2), and C (3) were isolated along with ergosterol from the mycelial chloroform extract of Aspergillus sp. NE-45. The structures of cycloaspeptides A. B, and C were established on the basis of chemical and spectroscopic evidence as 1, 2, and 3, respectively. Cycloaspeptides are new cyclic pentapeptides containing an anthranilic acid residue and two N-methyl amino acid residues.

  从曲霉 NE-45 菌丝体氯仿提取物中分离出三种新化合物，分别命名为环肽 A（1）、B（2）和 C（3）。根据化学和光谱证据，确定环肽 A、B 和 C 的结构分别为 1、2 和 3。环肽是一种新的环状五肽，含有一个蚁酸残基和两个 N-甲基氨基酸残基。
• Compounds for the treatment of diseases associated with amyloid or amyloid-like proteins
  申请人：Kroth Heiko

  公开号：US09221812B2

  公开（公告）日：2015-12-29

  The present invention relates to novel compounds that can be employed in the treatment of a group of disorders and abnormalities associated with amyloid protein, such as Alzheimer's disease, and of diseases or conditions associated with amyloid-like proteins. The compounds of the present invention can also be used in the treatment of ocular diseases associated with pathological abnormalities/changes in the tissues of the visual system. The present invention further relates to pharmaceutical compositions comprising these compounds and to the use of these compounds for the preparation of medicaments for treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins. A method of treating or preventing diseases or conditions associated with amyloid and/or amyloid-like proteins is also disclosed.

  本发明涉及一类新化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常，如阿尔茨海默病，以及与淀粉样蛋白类似蛋白质相关的疾病或病况。本发明的化合物还可用于治疗与视觉系统组织病理性异常/变化相关的眼部疾病。本发明还涉及包含这些化合物的制药组合物，以及使用这些化合物制备治疗或预防与淀粉样和/或淀粉样类似蛋白质相关的疾病或病况的药物的用途。还公开了一种治疗或预防与淀粉样和/或淀粉样类似蛋白质相关的疾病或病况的方法。
• Simple and efficient preparation of (R)- and (S)-enantiomers of ?-carbon deuterium-labelled ?-amino acids
  作者：Goran Mitulovi、Michael L�mmerhofer、N. M. Maier、Wolfgang Lindner

  DOI：10.1002/(sici)1099-1344(200004)43:5<449::aid-jlcr331>3.0.co;2-0

  日期：2000.4