alpha-(乙酰基氨基)乙酰基乙酸乙酯 | 5431-93-6

• 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: alpha-(乙酰基氨基)乙酰基乙酸乙酯
• 中文别名: 2-乙酰氨基-3-氧代-丁酸乙基酯
• 英文名称: ethyl 2-(acetylamino)-3-oxobutanoate
• 英文别名: ethyl 2-acetamido-3-oxobutanoate；ethyl α-acetylamino-β-ketobutyrate；ethyl 2-acetamido-3-oxobutyrate
• CAS: 5431-93-6
• 化学式: C₈H₁₃NO₄
• mdl: MFCD09761211
• 分子量: 187.196
• InChiKey: YUXXFBQECDBUIB-UHFFFAOYSA-N

物化性质

• 熔点：
  141 °C
• 沸点：
  125-132 °C(Press: 3-4 Torr)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-acetamido-3-oxobutanoate
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: Ethyl 2-acetamido-3-oxobutanoate
CAS number: 5431-93-6

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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, refrigerated.
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: C8H13NO4
Molecular weight: 187.2

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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：

  alpha-(乙酰基氨基)乙酰基乙酸乙酯 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 (2,5-二甲基-1,3-噁唑-4-基)甲醇
  参考文献：
  名称：

  蛋白质-配体复合物的设计、合成和 X 射线结构：Memapsin 2（β-分泌酶）抑制剂选择性的重要见解

  摘要：

  描述了 memapsin 2 蛋白质-配体复合物的基于结构的设计、合成和 X 射线结构。这些抑制剂专门设计用于与 S2 和 S3 活性位点残基相互作用，以提供对 memapsin 1 和组织蛋白酶 D 的选择性。抑制剂 6 对 memapsin 2 表现出极强的抑制活性，并且对 memapsin 1（>3800 倍）和组织蛋白酶具有选择性D（>2500 倍）。蛋白质-配体晶体结构揭示了 memapsin 2 的 S2 和 S3 活性位点中的协同相互作用。这些相互作用可以作为设计 memapsin 1 和组织蛋白酶 D 选择性的重要指南。

  DOI：

  10.1021/ja058636j
• 作为产物：
  描述：

  2-hydroxyiminoacetoacetic acid ethyl ester 在 钯 氢气 、 乙酸酐 作用下， 以92.3%的产率得到alpha-(乙酰基氨基)乙酰基乙酸乙酯
  参考文献：
  名称：

  2-amido-3-aminocarboxylic acid esters and process of preparation thereof

  摘要：

  2,3-二氨基羧酸化合物的制备方法为：(A)硝化β-酮酸酯，形成3-酮基-2-肟酯；(B)将得到的肟转化为保护的2-胺基；(C)还原性地氨化保护的2-胺基的3-位，形成2,3-二氨基羧酸酯，其中2-胺基团是保护的；(D)如有需要，处理2,3-二氨基羧酸酯，去除一个或多个氨基和羧基的保护基。

  公开号：

  US04593118A1
• 作为试剂：
  描述：

  2-(羟亚氨基)乙酰乙酸乙酯 、 乙酸酐 、 氢气 在 钯 silica gel 、 乙酸乙酯 、 正庚烷 、 alpha-(乙酰基氨基)乙酰基乙酸乙酯 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以to give the titled compound of ethyl 2-acetoamido-3-oxobutanoate 10.5 g (yield 90%)的产率得到alpha-(乙酰基氨基)乙酰基乙酸乙酯
  参考文献：
  名称：

  METHOD FOR PREPARING (2RS)-AMINO-(3S)-HYDROXY-BUTYRIC ACID AND ITS DERIVATIVES

  摘要：

  本发明涉及一种使用化学合成和酶还原反应，在高产率和高纯度下轻松制备手性氨基酸(2RS)-氨基-(3S)-羟基丁酸的方法，以及制备该中间体的方法。

  公开号：

  US20160017389A1

文献信息

• [EN] PYRIDINONE- AND PYRIDAZINONE-BASED COMPOUNDS AND MEDICAL USES THEREOF<br/>[FR] COMPOSÉS À BASE DE PYRIDINONE ET DE PYRIDAZINONE ET UTILISATIONS MÉDICALES ASSOCIÉES
  申请人：HLA TIMOTHY

  公开号：WO2019173790A1

  公开（公告）日：2019-09-12

  The various examples presented herein are directed to compounds of the formula A-L1-Het1-L2-Cy1 or a pharmaceutical acceptable salt, polymorph, prodrug, solvate or clathrate thereof, wherein: A is cycloalkyl, aryl, arylalkyl or heterocyclyl; Het1 is heterocyclyl containing at least two heteroatoms; Cy1 is a heterocyclyl; L1 is a bond, alkyl, alkenyl or alkynyl linker; L2 is an acyl or alkyl linker; and A and Cy1 are different. The compounds are useful in the treatment of fibrotic diseases, abnormal vascular leak and pathological angiogenesis.

  本文提供的各种示例涉及到以下公式的化合物A-L1-Het1-L2-Cy1或其药用可接受的盐、多型体、前药、溶剂合物或包合物，其中：A为环烷基、芳基、芳基烷基或杂环烷基；Het1为含有至少两个杂原子的杂环烷基；Cy1为杂环烷基；L1为键、烷基、烯基或炔基连接物；L2为酰基或烷基连接物；A和Cy1不同。这些化合物在治疗纤维化疾病、异常血管渗漏和病理性血管生成方面具有用途。
• [EN] BICYCLIC COMPOUNDS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF<br/>[FR] COMPOSES BICYCLIQUES INHIBANT L'ACTIVITE DE LA BETA-SECRETASE ET PROCEDES D'UTILISATION ASSOCIES
  申请人：ZAPAQ INC

  公开号：WO2006034277A1

  公开（公告）日：2006-03-30

  The present invention provides bicyclic beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer’s disease.

  本发明提供了双环β-分泌酶抑制剂及其用途，包括用于治疗阿尔茨海默病的方法。
• Compounds and methods which modulate feeding behavior and related diseases
  申请人：Amgen Inc.

  公开号：US06187777B1

  公开（公告）日：2001-02-13

  There are provided compounds, compositions and methods of use thereof in the modulation of feeding behavior, obesity, diabetes, cancer (tumor), inflammatory disorders, depression, stress related disorders, Alzheimer's disease and other disease conditions.

  提供了化合物、组合物及其使用方法，用于调节进食行为、肥胖、糖尿病、癌症（肿瘤）、炎症性疾病、抑郁症、与压力相关的疾病、阿尔茨海默病和其他疾病状况。
• HETEROCYCLIC SUBSTITUTED TRIFLUOROMETHYL PYRIMIDINONES AND THEIR USE
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160237059A1

  公开（公告）日：2016-08-18

  The present application relates to novel heterocyclically substituted 6-(trifluoromethyl)pyrimidin-4(3H)-one derivatives, to processes for their preparation, to their use alone or in combinations for the treatment and/or prevention of diseases, and to their use for preparing medicaments for the treatment and/or prevention of diseases, in particular for treatment and/or prevention of cardiovascular, renal, inflammatory and fibrotic diseases.

  本申请涉及新颖的杂环取代的6-(三氟甲基)嘧啶-4(3H)-酮衍生物，其制备方法，它们单独或组合用于治疗和/或预防疾病，以及它们用于制备用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管、肾脏、炎症和纤维化疾病。
• Amino-Containing Compounds Which Inhibit Memapsin 2 Beta-Secretase Activity and Methods of Use Thereof
  申请人：Ghosh Arun K.

  公开号：US20080125467A1

  公开（公告）日：2008-05-29

  The present invention provides novel beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer's disease.

  本发明提供了新型β-分泌酶抑制剂及其使用方法，包括治疗阿尔茨海默病的方法。