N-(对甲苯基磺酰氨基)-DL-丙氨酸 | 21957-58-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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: N-(对甲苯基磺酰氨基)-DL-丙氨酸
• 中文别名: 2-(甲苯-4-磺酰基氨基)-丙酸；N-(对甲苯磺酰基)-DL-丙氨酸；2-(对甲苯基磺酰氨基)丙酸
• 英文名称: N-(p-toluenesulfonyl)-DL-alanine
• 英文别名: 2-{(4-methylphenylsulphonyl)amino}propanoic acid；2-(4-methylbenzenesulfonylamino)propionic acid；2-(toluene-4-sulfonylamino)propionic acid；N-p-toluenesulphonyl-alanine；N-tosyl-DL-alanine；2-[[(4-Methylphenyl)sulfonyl]amino]propanoic acid；2-[(4-methylphenyl)sulfonylamino]propanoic acid
• CAS: 21957-58-4；85471-45-0；4816-81-3
• 化学式: C₁₀H₁₃NO₄S
• mdl: MFCD00230250
• 分子量: 243.284
• InChiKey: LQXKHFZRJYXXFA-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139℃
• 沸点：
  428.9±55.0 °C(Predicted)
• 密度：
  1.319
• 溶解度：
  易溶于可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  Refrigerator

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Tosyl-l-alanine
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: N-Tosyl-l-alanine
CAS number: 99076-56-9

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H13NO4S
Molecular weight: 243.3

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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, sulfur 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide	114663-10-4	C10H15NO3S	229.3

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 2-(4-methylphenylsulfonamido)propanoate	——	C11H15NO4S	257.31
  ——	N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide	114663-10-4	C10H15NO3S	229.3
  ——	N-p-toluenesulfonyl-L-alanyl chloride	——	C10H12ClNO3S	261.729
  ——	N-(p-toluenesulfonyl)-d,l-alanyl chloride	56271-34-2	C10H12ClNO3S	261.729
  ——	4-methyl-N-(1-oxopropan-2-yl)-N-prop-2-enylbenzenesulfonamide	147048-45-1	C13H17NO3S	267.349
  ——	N-Allyl-N-toluene-p-sulfonyl-(DL)-alanine methyl ester	147048-44-0	C14H19NO4S	297.375
  4-甲基-3-(4-甲基苯基)磺酰基-1,3-恶唑烷-5-酮	4-methyl-3-(p-tolylsulfonyl-5-oxazolidinone)	62188-31-2	C11H13NO4S	255.295
  ——	N-(1-methyl-2-oxo-2-anilinoethyl)-p-toluenesulphonamide	101289-30-9	C16H18N2O3S	318.397
  ——	N-Allyl-N-(4,4-dibromobut-3-en-2-yl)toluene-p-sulfonamide	147048-43-9	C14H17Br2NO2S	423.168

反应信息

• 作为反应物：
  描述：

  N-(对甲苯基磺酰氨基)-DL-丙氨酸 在 氧气 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以54%的产率得到对甲苯磺酰胺
  参考文献：
  名称：

  Cu(II)-催化脱羧/消除N-芳基磺酰基氨基酸生成伯芳基磺酰胺

  摘要：

  摘要开发了一种用于 CuO 催化脱羧/消除 N-芳基磺酰基氨基酸的新方案。这是使用可接近的氨基酸作为氨合成等价物通过氧化脱羧/消除反应合成伯芳基磺酰胺的第一个例子。本协议显示出优异的官能团耐受性，并为以优异的产率合成伯芳基磺酰胺提供了一种有效的方法。图形概要

  DOI：

  10.1080/00397911.2016.1202981
• 作为产物：
  描述：

  Tos-DL-Ala-DMPir 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以97%的产率得到N-(对甲苯基磺酰氨基)-DL-丙氨酸
  参考文献：
  名称：

  酰基吡唑的直接催化化学选择性 α-胺化：非天然 α-氨基酸衍生物的简洁途径

  摘要：

  描述了直接铜催化的高化学选择性 α-胺化。酰基吡唑被证明是羧酸氧化态底物的高效烯醇前体，而通过化学计量的强碱预活化已用于催化 α-胺化。偶联伙伴的同时活化、烯醇化和金属氮烯化合物的形成对于获得产品至关重要，广泛的官能团兼容性突出了本催化的温和性。双齿配位模式适用于对酮和更多酸性硝基烷基官能团的高度化学选择性活化。氘交换实验清楚地表明，在不形成硝酸盐的情况下实现了酰基吡唑的排他性烯醇化。目前的催化作用应用于后期 α-胺化，可以简明地获得高度通用的 α-氨基酸衍生物。该产品可以转化为各种有用的积木。

  DOI：

  10.1021/jacs.5b11773

文献信息

• Chiral discrimination of α-hydroxy acids and N-Ts-α-amino acids induced by tetraaza macrocyclic chiral solvating agents by using ¹H NMR spectroscopy
  作者：Caixia Lv、Lei Feng、Hongmei Zhao、Guo Wang、Pericles Stavropoulos、Lin Ai

  DOI：10.1039/c6ob02578a

  日期：——

  In the field of chiral recognition, reported chiral discrimination by 1H NMR spectroscopy has mainly focused on various chiral analytes with a single chiral center, regarded as standard chiral substrates to evaluate the chiral discriminating abilities of a chiral auxiliary. Among them, chiral α-hydroxy acids, α-amino acids and their derivatives are chiral organic molecules involved in a wide variety

  在手性识别领域，已报道的1 H NMR光谱手性判别主要集中于具有单一手性中心的各种手性分析物，将其作为标准手性底物来评估手性助剂的手性判别能力。其中，手性α-羟基酸、α-氨基酸及其衍生物是手性有机分子，参与多种生物过程，在药物制备领域也发挥着重要作用，因为它们是合成药物的一部分。手性药物中间体和蛋白质药物的生产过程。在本文中，使用几种α-羟基酸和N -Ts-α-氨基酸通过1 H NMR波谱评估了四氮杂大环手性溶剂化剂(TAMCSA) 1a-1d的手性辨别能力。结果表明，在大多数情况下，在TAMCSA 1a-1d存在的情况下，通过1 H NMR 光谱可以成功区分 α-羟基酸和N -Ts-α-氨基酸。α-羟基酸和N -Ts-α-氨基酸的对映体是根据相应质子的1 H NMR信号积分的变化来指定的。根据(R )-和( R )-对映体的CH 3质子(Ts基团)的1 H NMR信号积分计算不同光学组成的N
• β-Cyclodextrin-Catalyzed Monosulfonylation of Amines and Amino Acids in Water
  作者：R. Sridhar、B. Srinivas、V. Pavan Kumar、M. Narender、K. Rama Rao

  DOI：10.1002/adsc.200600652

  日期：2007.8.6

  A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.

  首次在仿生条件下开发了一种温和而有效的方法，用于室温下水中β-环糊精催化的各种胺和氨基酸的单磺酰化反应，从而以高收率提供相应的磺酰胺。
• Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
  作者：Kyalo Stephen Kanyiva、Kanako Uchida、Takanori Shibata

  DOI：10.1246/bcsj.20200393

  日期：2021.4.15

  We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a

  我们描述了一种简单实用的方案，用于使用容易获得的甲苯衍生物和α-氨基酸磺酰胺合成苄基砜。在银催化下，反应进行以中等至高收率提供了广泛范围的苄基砜。该机理可能涉及α-氨基烷基基团的Minisci型形成，NS键的均相裂解以产生磺酰基基团，以及磺酰基基团与经由硫酸根阴离子自由基的氢提取形成的苄基基团偶联。该反应的实用性通过抗癌活性化合物的克级合成和一步合成来证明。研究的机理是通过使用自由基清除剂和氘代甲苯进行的。
• [EN] NRF2 REGULATORS<br/>[FR] RÉGULATEURS DE NRF2
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016202253A1

  公开（公告）日：2016-12-22

  Provided are aryl analogs，pharmaceutical compositions containing them and their use as NRF2 regulators.

  提供芳基类似物，含有它们的药物组合物以及它们作为NRF2调节剂的用途。
• Palladium-catalyzed site-selective hydrogen isotope exchange (HIE) reaction of arylsulfonamides using amino acid auxiliary
  作者：Wei Liu、Xingyu Xu、Hongyan Zhao、Xiaoyu Yan

  DOI：10.1016/j.tet.2018.06.024

  日期：2018.7

  Hydrogen isotope exchange (HIE) is a versatile method for the introduction of deuterium to organic compounds. Herein, regioselective deuteration of sulfonamides is achieved by palladium-Catalyzed HIE reaction. By using amino acid as weakly coordination-directing auxiliary, a variety of sulfonamides are efficiently deuterated at the ortho-position. Placing competing directing groups on the aromatic

  氢同位素交换（HIE）是将氘引入有机化合物的一种通用方法。在本文中，磺酰胺的区域选择性氘化是通过钯催化的HIE反应实现的。通过使用氨基酸作为弱配位导向助剂，多种磺酰胺在邻位被有效地氘化。在芳族环上放置竞争性的导向基团不影响位点选择性。