2-乙酰氨基-3-甲基戊酸 | 3077-46-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 异亮氨酸类衍生物
• 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: 2-乙酰氨基-3-甲基戊酸
• 英文名称: N-acetyl-isoleucine
• 英文别名: N-Acetyl-isoleucin；N-Acetylisoleucine；2-acetamido-3-methylpentanoic acid
• CAS: 3077-46-1；19764-31-9；33601-90-0；20257-17-4
• 化学式: C₈H₁₅NO₃
• mdl: MFCD00278267
• 分子量: 173.212
• InChiKey: JDTWZSUNGHMMJM-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  369.7±25.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微、加热）、DMF（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  Store at room temperature.

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Acetyl-l-isoleucine
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-Acetyl-l-isoleucine
CAS number: 3077-46-1

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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: C8H15NO3
Molecular weight: 173.2

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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

制备方法与用途

N-乙酰-L-异亮氨酸

N-乙酰-L-异亮氨酸是L-异亮氨酸的乙酰化产物，可通过一步反应由L-异亮氨酸与醋酐制备得到。该化合物作为一种重要的精细有机化工中间体，在医药、农药及化学工业等多个领域有广泛应用。

制备方法

在250毫升圆底烧瓶中，将15克（114毫摩尔）的L-异亮氨酸和31克（304毫摩尔）乙酸酐溶解于50毫升甲醇中，得到白色混悬液。回流搅拌5.5小时后，减压浓缩反应混合物，并从乙醇中重结晶，最终得到13.3克白色晶体。

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-3-甲基戊酸 、 三丁基氧化锡 以 甲苯 为溶剂， 生成 N-acetyl-DL-CH3CH2CH(CH3)CHNHCOO-tri-n-butyltin
  参考文献：
  名称：

  119Sn-NMR-spektroskopische Untersuchungen an Tri-n-butylzinnderivaten von N-Acetylaminos�uren

  摘要：

  Eleven compounds have been prepared by azeotropic destillation of water from toluene solutions of bi(tri-n-butyltin)oxide and N-acetyl amino acids. All derivatives are white solids. Sn-119-NMR-spectra of the tri-n-butyltin compounds have been studied in coordinating and non coordinating solvents. The chemical shifts and the coupling constants 1J(Sn-119, C-13) depend significantly on the coordination number of the tin atom and on the properties of the substituents. The data for the compounds are discussed in comparison with those for other tri-n-butyltin compounds.

  DOI：

  10.1007/bf00812329
• 作为产物：
  描述：

  乙酰胺 、 反-2-丁烯 、 一氧化碳 在 三(三苯基膦)羰基氢化铑 、 dicobalt octacarbonyl 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以34%的产率得到2-乙酰氨基-3-甲基戊酸
  参考文献：
  名称：

  Syngas reactions

  摘要：

  The amidocarbonylation of olefin and aldehyde substrates has been applied to the synthesis of a variety of amidocarboxylic acids, including surface active agents (e.g. C-14-C-16 N-acyl-alpha-amino acids), specialty surfactants (such as the sarcosinates), intermediates for sweeteners (e.g. aspartame), food additives (e.g. glutamic acid), and certain chelating agents. Homogeneous cobalt and rhodium-based catalysts, modified, for example, with sulfoxide and bidentate phosphine ligands, have been tailored to the synthesis of each individual class of product. Process studies, including examinations of reaction rate, product selectivity, as well as catalyst stability, have been undertaken for N-acetylglycine and amido acid surfactant syntheses.

  DOI：

  10.1016/0022-328x(91)80164-f

文献信息

• [EN] LEVORPHANOL PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE LEVORANOL ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191472A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and vitamin compounds chemically conjugated to levorphanol ((-)-17-methylmorphinan-3-ol) to form novel prodrugs and compositions of levorphanol.

  目前描述的技术提供了一种或多种羟基酸、聚乙二醇和维生素化合物与左旋吗啡醇((-)-17-甲基吗啡-3-醇)在化学上结合形成新型前药和左旋吗啡的组合物。
• Photoredox/Cobalt Dual‐Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
  作者：Kaitie C. Cartwright、Ebbin Joseph、Chelsea G. Comadoll、Jon A. Tunge

  DOI：10.1002/chem.202001952

  日期：2020.9.25

  Recently, dual‐catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N‐acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's

  近来，用于羧酸脱羧消除的双重催化策略已引起关注。我们的实验室以前曾报道过光氧化还原/钴肟双催化方法，该方法可直接从N酰基氨基酸合成酰胺和烯甲酸酯，并避免使用任何化学计量试剂。本文详述的进一步开发改进了这种转化的用途，进一步的实验为反应机理提供了新的见解。这些新的发展和见识有望帮助扩大光氧化还原/钴双催化系统。
• [EN] DEXTRORPHAN PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE DEXTRORPHANE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191477A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and/or vitamin compounds chemically conjugated to dextrorphan, (+)-17-methylmorphinan-3-ol), to form novel prodrugs and compositions of dextrorphan.

  目前描述的技术提供了将一种或多种羟基酸、聚乙二醇和/或维生素化学共轭到右旋丙啡醇（(+)-17-甲基吗啡酮-3-醇）上，形成新型前药和右旋丙啡醇组合物的配方。
• METHODS FOR meta-ARYLATION OF AROMATIC ALCOHOLS
  申请人：The University of Georgia Research Foundation, Inc

  公开号：US20180065909A1

  公开（公告）日：2018-03-08

  Provided are methods for the meta-selective C—H arylations of arene alcohol-based substrates. The methods combine the transient norbornene strategy with a quinoline-based acetal scaffold to achieve the formation of biaryl compounds. These processes establish a foundation for catalytic polyfunctionalization of alcohol-based compounds. The method comprises attaching a heterocyclic hemiacetal scaffold to an aromatic alcohol or a substituted aromatic alcohol; reacting the aromatic or substituted aromatic alcohol having the heterocyclic hemiacetal scaffold attached with an alkyl or aryl iodide in a reaction mix comprising a palladium catalyst, a silver salt, and carboxymethyl norbornene to generate a meta-arylated arene conjugated to the heterocyclic hemiacetal scaffold; and then cleaving the heterocyclic hemiacetal scaffold from the meta-arylated arene alcohol.

  提供了一种用于基于芳烃醇的底物的C—H芳基化的方法。这些方法将瞬时的去氢脱环戊烯策略与基于喹啉的缩醛支架相结合，以实现双芳基化合物的形成。这些过程为醇基化合物的催化多官能化奠定了基础。该方法包括将一个杂环半缩醛支架连接到芳香醇或取代芳香醇上；将具有连接有杂环半缩醛支架的芳香或取代芳香醇与一种含有钯催化剂、银盐和羧甲基去氢脱环戊烯的反应混合物中的烷基或芳基碘反应，以生成连接到杂环半缩醛支架的间位芳基化芳烃；然后从间位芳基化芳醇中裂解杂环半缩醛支架。
• Cosmetic composition
  申请人：UNILEVER PLC

  公开号：EP0415598A1

  公开（公告）日：1991-03-06

  A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from N-acylated amino-acids, in which the acyl group has from 2 to 20 carbon atoms, together with a cosmetically acceptable vehicle for the hair growth promoter.

  适用于哺乳动物皮肤和头发的局部应用的组合物，用于诱导、维持或增加头发生长，包括选择自N-酰化氨基酸的头发生长促进剂，其中酰基含有2至20个碳原子，以及用于头发生长促进剂的化妆品可接受载体。