N-(4-硝基苯磺酰)-L-苯丙氨酸氯 | 146815-23-8

• 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-(4-硝基苯磺酰)-L-苯丙氨酸氯
• 中文别名: N-(4-硝基苯己亚磺酰基)-L-苯丙氨氯；N-(4-硝基苯磺酰)-L-苯丙氨酰氯
• 英文名称: N-nosyl-L-phenylalanine chloride
• 英文别名: N-(4-Nitrophenylsulfonyl)-L-phenylalanyl Chloride；(2S)-2-[(4-nitrophenyl)sulfonylamino]-3-phenylpropanoyl chloride
• CAS: 146815-23-8
• 化学式: C₁₅H₁₃ClN₂O₅S
• 分子量: 368.798
• InChiKey: RYQIQECSYJRDBT-AWEZNQCLSA-N

物化性质

• 熔点：
  149 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090
• 储存条件：
  室温

SDS

N-(4-Nitrophenylsulfonyl)-L-phenylalanyl Chloride
[Optical Resolving Reagent]
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: N-(4-Nitrophenylsulfonyl)-L-phenylalanyl Chloride [Optical Resolving Reagent]

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Warning
Signal word
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
N-(4-Nitrophenylsulfonyl)-L-phenylalanyl Chloride [Optical Resolving Reagent]
Components:
Percent: >98.0%(T)
146815-23-8
CAS Number:
Chemical Formula: C15H13ClN2O5S

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
N-(4-Nitrophenylsulfonyl)-L-phenylalanyl
Chloride [Optical Resolving Reagent]

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. 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.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, carbon dioxide.
media:
Unsuitable extinguishing Water
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: 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: Remove movable
containers 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
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
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 Do not allow contact with water. Remove all sources of ignition. Fire-extinguishing
hazards: devices should be prepared in 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.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
May develop pressure. Open carefully.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Moisture-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
N-(4-Nitrophenylsulfonyl)-L-phenylalanyl
Chloride [Optical Resolving Reagent]

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
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
Solid
Physical state (20°C):
Form: Crystal- Powder
Colour: Very pale yellow - Yellow
Odour: No data available
pH: No data available
Melting point/freezing point:149°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]
Soluble: Dioxane

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous Decomposes in contact with water and liberates toxic gases.
reactions:
Conditions to avoid: Moisture
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides, Hydrogen
chloride
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:
No data available
Fish:
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
No data available
Soil adsorption (Koc):
N-(4-Nitrophenylsulfonyl)-L-phenylalanyl
Chloride [Optical Resolving Reagent]

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Section 12. ECOLOGICAL INFORMATION
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. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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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

反应信息

• 作为反应物：
  描述：

  N-(4-硝基苯磺酰)-L-苯丙氨酸氯 在 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 1.5h， 生成 N-(N-methyl-N-nosyl-L-phenylalanyl)-L-alanine methyl ester
  参考文献：
  名称：

  溶液相中肽链延伸过程中选定位置上肽的N-甲基化

  摘要：

  已经开发了一种用于肽的位点特异性N-甲基化的有效且通用的溶液相方法。这种新颖的方法涉及N-烷基保护的肽的合成及其随后与重氮甲烷的N-甲基化。通过成功合成具有N-甲基氨基酸残基的各种受阻寡肽，具有优异的收率和纯度，证明了其效率。该方法特别吸引人，因为所采用的条件不会引起肽立体中心的任何可检测的外消旋化，并且该方法不需要对甲基化产物进行色谱纯化。另一个优点是该方法与Fmoc溶液相肽合成的兼容性。

  DOI：

  10.1021/jo0478959
• 作为产物：
  描述：

  L-苯丙氨酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-硝基苯磺酰)-L-苯丙氨酸氯
  参考文献：
  名称：

  ñ -甲基- Ñ -nosyl-β 3 -氨基酸

  摘要：

  ñ -甲基β 3 -氨基酸是生物活性分子的合成中重要构建块。一个非常简单的和有效的方法来改造天然α氨基酸为它们相应的ñ -甲基- β 3 -氨基酸这里提出。在该方法中，关键中间体N-甲基-N-糖基-α-氨基酰基重氮甲烷只需一步即可制备，只需对相应的N进行简单处理即可。-重氮甲烷制的β-糖基-α-氨基酰氯。合成途径利用了nosyl基团的优势。该N-掩蔽部分激活NH功能，并且可以在重氮甲烷的酰化步骤，渲染代替被示出为在所有已经报道的制备中的经典程序必要无用的第二步骤中直接发生N-甲基化ñ -甲基β 3 -氨基酸。的沃尔夫重排反应Ñ甲基Ñ -nosyl-α-aminoacyldiazomethanes提供了相应的Ñ甲基Ñ -nosyl-β 3-氨基酸具有完全保留的起始α-氨基酸的手性构型。手性碳原子的无差向异构化，也观察到当Ñ甲基Ñ -nosyl-β 3 -氨基酸被转变成氯化物和耦合用α-氨基酸

  DOI：

  10.1021/jo070438i

文献信息

• Scavenger assisted combinatorial process for preparing libraries of amides, carbamates and sulfonamides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0825164A2

  公开（公告）日：1998-02-25

  This invention relates to a novel solution phase process for the preparation of amide, carbamate, and sulfonamide combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

  这项发明涉及一种用于制备酰胺、碳酸酯和磺酰胺组合库的新型溶液相过程。这些库在药物发现中具有实用价值，并用于形成新型检测套件的微孔板组件。
• Site-Selective Methylation of <i>N</i>^β-Nosyl Hydrazides of <i>N</i>-Nosyl Protected α-Amino Acids
  作者：Rosaria De Marco、Antonella Leggio、Angelo Liguori、Tiziana Marino、Francesca Perri、Nino Russo

  DOI：10.1021/jo1003168

  日期：2010.5.21

  methylation reaction of Nβ-nosyl hydrazides of N-nosyl protected α-amino acids by using diazomethane shows a controlled regiochemical trend and makes it possible to obtain the corresponding products methylated at specific positions depending on the amount of diazomethane used. The observed selectivity is closely connected with the different acidity of sulfonyl hydrazide, sulfonamide, and acyl hydrazine protons

  的甲基化反应Ñ β -nosyl的酰肼Ñ通过使用重氮甲烷示出了受控区域化学趋势和-nosyl保护α氨基酸，能够获得以取决于重氮甲烷的使用量的特定位置甲基化相应的产品。观察到的选择性与分析底物中存在的磺酰肼，磺酰胺和酰基肼质子的不同酸度密切相关。理论计算支持了这三个不同反应位点的反应顺序。在这项工作中考虑的肼衍生物属于一类具有令人感兴趣的生物活性并且对有机合成非常感兴趣的化合物。
• NMR Separation of β-Prochiral Protons to the Ether Oxygen of Chiral Esters with Lanthanide Shift Reagents
  作者：James M. Coxon、James R. A. Cambridge、Shayne G. C. Nam

  DOI：10.1021/ol016904m

  日期：2001.12.1

  The use of chiral ester derivatives of 2-phenylethan-1-ol in conjunction with chiral lanthanide shift reagents allows separation of the prochiral and homo prochiral protons to the ether oxygen in the NMR spectrum. Specifically the alpha- and beta- protons of the N-(4-nitrophenylsulfonyl)-L-phenylalanyl ester of 2-phenylethan-1-ol, after addition of either europium d- or l-3-heptafluorobutyrylcamphorate

  将2-苯基乙-1-醇的手性酯衍生物与手性镧系元素转移试剂结合使用可在NMR光谱中将前手性和均手性质子分离为醚氧。具体地，在添加eurod-或l-3-七氟丁酰樟脑或ord-3-之后，2-苯基乙-1-醇的N-（4-硝基苯基磺酰基）-L-苯丙氨酸酯的α-和β-质子区分七氟丁酰樟脑酯。这是前手性质子β与酯键的NMR分离的首次报道。[反应：看文字]
• Silver acetate-assisted formation of amides from acyl chlorides
  作者：A. Leggio、E.L. Belsito、M.L. Di Gioia、V. Leotta、E. Romio、C. Siciliano、A. Liguori

  DOI：10.1016/j.tetlet.2014.11.067

  日期：2015.1

  acid chlorides to give amides is disclosed. Reactions are carried out in the presence of silver acetate in non-aqueous environments under heterogeneous phase conditions. Amides are easily recovered in very good to excellent yields and without racemization. The approach is successful in forming peptide bonds starting from N-(4-nitrobenzenesulfonyl)-amino acid chlorides and allows the formation of dipeptides

  公开了一种温和的方法用于羧酰氯的氨解以产生酰胺。反应在乙酸银存在下在非水环境中在非均相条件下进行。酰胺很容易以非常高的收率回收，而且没有外消旋作用。该方法成功地形成了从N-（4-硝基苯磺酰基）-氨基酸氯化物开始的肽键，并且当使用N-甲基化的氨基酸衍生物时也允许形成二肽。
• Lewis acid catalysed methylation of<i>N</i>-(9H-fluoren-9-yl)methanesulfonyl (Fms) protected lipophilic<i>α</i>-amino acid methyl esters
  作者：Antonella Leggio、Danila Alò、Emilia Lucia Belsito、Maria Luisa Di Gioia、Emanuela Romio、Carlo Siciliano、Angelo Liguori

  DOI：10.1002/psc.2777

  日期：2015.8

  This work reports an efficient Lewis acid catalysed N‐methylation procedure of lipophilic α‐amino acid methyl esters in solution phase. The developed methodology involves the use of the reagent system AlCl3/diazomethane as methylating agent and α‐amino acid methyl esters protected on the amino function with the (9H‐fluoren‐9‐yl)methanesulfonyl (Fms) group. The removal of Fms protecting group is achieved

  这项工作报告了一种有效的路易斯酸催化溶液相中亲脂性α-氨基酸甲基酯的N-甲基化过程。该改进的方法包括使用该试剂系统的AlCl的3 /重氮甲烷作为甲基化试剂和α上的氨基功能保护与（9H-芴-9-基）甲磺酰（FMS）基团-氨基甲酸甲基酯。Fms保护基的去除在与用于Fmoc去除的那些条件相同的条件下实现。因此，在合成N时，Fms基团可与Fmoc基团互换。使用基于标准Fmoc的策略对甲基化的肽进行分析。最后，通过合成一对非对映异构二肽证明在甲基化反应过程中不存在外消旋作用和Fms基团的去除。版权所有©2015欧洲肽协会和John Wiley＆Sons，Ltd.