2-氨基-N-甲基乙酰胺 | 22356-89-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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-氨基-N-甲基乙酰胺
• 英文名称: glycine methylamide
• 英文别名: 2-amino-N-methylacetamide；glycine N-methylamide；N-methylglycinamide
• CAS: 22356-89-4
• 化学式: C₃H₈N₂O
• mdl: MFCD06375945
• 分子量: 88.1093
• InChiKey: UUYDPHCMCYSNAY-UHFFFAOYSA-N

物化性质

• 沸点：
  275.6±23.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温和干燥环境

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-N-methylacetamide
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: 2-Amino-N-methylacetamide
CAS number: 22356-89-4

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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: C3H8N2O
Molecular weight: 88.1

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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：

  2-氨基-N-甲基乙酰胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到聚甘氨酸
  参考文献：
  名称：

  Macrocyclic compounds as metalloprotease inhibitors

  摘要：

  这项发明涉及抑制金属蛋白酶（包括聚集素酶）和肿瘤坏死因子（TNF）产生的大环分子。具体来说，这些化合物是涉及组织降解的金属蛋白酶的抑制剂，也是肿瘤坏死因子释放的抑制剂。本发明还涉及包括这些化合物的药物组合物，以及使用这些化合物治疗炎症性疾病的方法。

  公开号：

  US06281352B1
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 在 甲胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.55h， 以77%的产率得到2-氨基-N-甲基乙酰胺
  参考文献：
  名称：

  Preparation of the MacMillan imidazolidinones

  摘要：

  A general method for the preparation of the MacMillan imidazolidinones is described. Treatment of an alpha-amino amide with a carbonyl compound in refluxing chloroform in the presence of Yb(OTf)(3) (1 mol %) provides convenient access to the corresponding imidazolidinones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.009
• 作为试剂：
  描述：

  4-碘苯甲醚 、 2-甲基苯甲醛 在 palladium diacetate 、 溶剂黄146 、 2-氨基-N-甲基乙酰胺 、 silver trifluoroacetate 作用下， 以 水 为溶剂， 以68 %的产率得到2-(4-methoxybenzyl)benzaldehyde
  参考文献：
  名称：

  使用 2-氨基-N-甲基-乙酰胺作为 L,L 型瞬态导向基团对芳香醛进行邻-C(sp3)-H 芳基化

  摘要：

  报道了使用 2-氨基-N-甲基-乙酰胺作为简单、高效且可商购的 L,L 型瞬态导向基团 (TDG)，对芳香醛进行 Pd 催化的邻-C(sp 3 )–H芳基化反应。该反应表现出优异的底物相容性，并以高达 78% 的中高收率生成所需的产物。还测试了进一步的酸催化环化和脱水芳构化，并提供了一些多环芳烃，收率高达 96%。2-甲基苯甲醛邻-C(sp 3)的X射线晶体结构)–H 钯化中间体得到。然后，提出了一种涉及形成 [5,6]-稠合钯环的合理反应机制。这种方法为开发新型 L、L 型 TDG 提供了宝贵的见解。

  DOI：

  10.1039/d3ob00024a

文献信息

• Enantioselective Direct α-Amination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling
  作者：Giuseppe Cecere、Christian M. König、Jennifer L. Alleva、David W. C. MacMillan

  DOI：10.1021/ja406181e

  日期：2013.8.7

  The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor

  醛的直接、不对称 α-胺化是通过光氧化还原和有机催化的组合完成的。光子生成的 N 中心自由基与催化形成的手性烯胺进行对映选择性 α-加成，直接产生具有合成有用胺取代模式的稳定 α-氨基醛加合物。在胺前体上引入光不稳定基团避免了在该转化中使用光氧化还原催化剂的需要。重要的是，这种光诱导转化允许直接和对映选择性地获得不需要反应后操作的 α-氨基醛产品。
• Effect of Monoelectronic Oxidation of an Unsymmetrical Phenoxido-Hydroxido Bridged Dicopper(II) Complex
  作者：Aurore Thibon-Pourret、Federica Gennarini、Rolf David、James A. Isaac、Isidoro Lopez、Gisèle Gellon、Florian Molton、Laurianne Wojcik、Christian Philouze、David Flot、Yves Le Mest、Marius Réglier、Nicolas Le Poul、Hélène Jamet、Catherine Belle

  DOI：10.1021/acs.inorgchem.8b02127

  日期：2018.10.1

  subunits. The X-ray crystal structure of 2(SbF6)(NO2) evidences that the nitrogen of the terminal amide group is protonated and the coordination of the amide occurs via the O atom. The bis-amide moiety appears to be a non-innocent proton acceptor along the redox process. Alternatively, protonation of complex 1 leads to the complex 2(ClO4)2, as evidenced by X-ray crystallography, cyclic voltammetry, and

  （μ-羟基，μ-苯氧基）Cu II Cu II配合物1是使用不对称配体合成的，该配体带有一个N，N-双（2-吡啶基）甲胺（BPA）部分，该部分配位一个铜和一个双阴离子双酰胺部分。配位其他铜离子。通过以金属为中心的过程，DMF中络合物的电化学单氧化在213 K下以E 1/2 = 0.12 V vs Fc + / Fc可逆地发生。产生的物种（复杂1 +）仅在低温下稳定，并且已通过UV-vis-NIR低温光谱电化学和EPR方法进行了光谱表征。与实验数据一致的DFT和TD-DFT计算支持形成Cu II Cu III苯氧基-羟基氧化物络合物。NOSbF 6低温化学氧化1会生成四核复合物2（SbF 6）（NO 2），该复合物显示出两个双核Cu II Cu II亚基。2（SbF 6）（NO 2）的X射线晶体结构）证明末端酰胺基团的氮被质子化并且酰胺的配位通过O原子发生。在氧化还原过程中，双酰胺部分似乎是
• [EN] 4 - (5 - ISOXAZOLYL OR 5 - PYRRAZOLYL -1,2,4- OXADIAZOL - 3 - YL) -MANDELIC ACID AMIDES AS SPHINGOSIN- 1 - PHOSPHATE 1 RRECEPTOR AGONISTS<br/>[FR] AMIDES D'ACIDE 4-(5-ISOXAZOLYL OU 5-PYRAZOLYL-1,2,4-OXADIAZOL-3-YL)-MANDÉLIQUE COMME AGONISTES DU RÉCEPTEUR DE LA SPHINGOSINE-1-PHOSPHATE DE TYPE 1
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011133734A1

  公开（公告）日：2011-10-27

  Disclosed are compounds of Formula (I) or stereoisomers, salts, or prodrugs thereof, wherein: Q is, or R1 is phenyl substituted with zero to 3 substituents; and R1, R2, R3, R4, R5, and G are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物或其立体异构体、盐或前药，其中：Q是，或者R1是苯基，其上取代基为零至3个；而R1、R2、R3、R4、R5和G在此处有定义。还揭示了将这些化合物用作G蛋白偶联受体S1P1的选择性激动剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓多种治疗领域的疾病或紊乱方面具有用处，如自身免疫疾病和血管疾病。
• Rates of Uncatalyzed Peptide Bond Hydrolysis in Neutral Solution and the Transition State Affinities of Proteases
  作者：Anna Radzicka、Richard Wolfenden

  DOI：10.1021/ja954077c

  日期：1996.1.1

  acetylglycylglycine, 600 years for the internal peptide bond of acetylglycylglycine N-methylamide, and 350 years for the dipeptide glycylglycine. These reactions, insensitive to changing pH or ionic strength, appear to represent uncatalyzed attack by water on the peptide bond. Comparison of rate constants indicates very strong binding of the altered substrate in the transition states for the corresponding enzyme reactions

  为了评估催化内部和 C 端肽键水解的酶的相对效率，在密封的石英管中在升高的温度下检查相应的非酶反应的速率，产生线性阿伦尼乌斯图。结果表明，在 25 °C 的中性溶液中，乙酰甘氨酰甘氨酸 C 端键的肽键水解半衰期约为 500 年，乙酰甘氨酰甘氨酸 N-甲酰胺的内部肽键的半衰期约为 600 年，而二肽甘氨酰甘氨酸。这些对 pH 值或离子强度变化不敏感的反应似乎代表了水对肽键的未催化攻击。速率常数的比较表明，相应酶反应的过渡态中改变的底物的结合非常强，
• Photoinduced electron transfer in aliphatic peptides
  作者：David Birch、John D. Coyle、Roger R. Hill、Graham E. Jeffs

  DOI：10.1039/c39860000293

  日期：——

  analysis in the photolysis of triglycine in neutral aqueous solution suggests that the initial intramolecular electron transfer from the carboxylate to the peptide group, shown to lead to efficient (ϕ 0.44 ± 0.11) photodegradation for glycylglycine, may be followed by transfer to the second peptide group.

  对三甘氨酸在中性水溶液中进行光解的产物分析表明，最初的分子内电子从羧酸盐转移至肽基团，显示出对甘氨酰甘氨酸的有效光降解（ϕ 0.44±0.11），之后可以转移至第二种肽团体。