methyl 2-acetamidoprop-2-enoate

• ChemBase编号: 150889
• 分子式: C6H9NO3
• 平均质量: 143.14056
• 单一同位素质量: 143.05824315
• SMILES: CC(=O)NC(=C)C(=O)OC
• Canonical SMILES: COC(=O)C(=C)NC(=O)C
• InChI: InChI=1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
• InChIKey: SMWNFFKPVLVOQQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 2-acetamidoprop-2-enoate
• IUPAC传统名: methyl 2-acetamidoprop-2-enoate
• 别名: 2-乙酰胺基丙烯酸甲酯; 2-乙酰氨基丙烯酸甲酯; Methyl 2-acetamidoacrylate; Ac-DL-Dha-OMe; 2-Acetamidoacrylic acid methyl ester

登记号

• CAS号: 35356-70-8
• MDL号: MFCD00013394
• Beilstein号: 1812208
• PubChem SID: 24859082; 162245049
• PubChem CID: 98644

理论计算性质

• Acid pKa: 12.697392
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.42481732
• LogD (pH = 7.4): -0.42481926
• Log P: -0.4248173
• 摩尔折射率: 35.1292 cm^3
• 极化性: 13.588454 Å^3
• 极化表面积: 55.4 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 49-51°C; 50-52 °C(lit.)
• 沸点: 103-104°C/8mm; 104 °C/8 mmHg(lit.)
• 闪点: 113 °C; 235.4 °F

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-37; 26-37/39
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 98%; 99%
• 线性分子式: H2C=C(NHCOCH3)CO2CH3

详细说明

Sigma Aldrich - 317519

包装
1, 5 g in glass bottle

参考文献

• Building block for amino acid synthesis.
• Heck coupling with 4-iodo-3,5-dimethylphenyl acetate, promoted by palladium acetate and Tri(o-tolyl)phosphine, A12093, is one of the key steps in a convenient asymmetric synthesis of the unnatural amino acid 2,6-dimethyl-L-tyrosine: Synthesis, 741 (1992).
• Asymmetric catalytic hydrogenation in supercritical carbon dioxide in the presence of a chiral rhodium catalyst gives the N-acetylalanine methyl ester in 99.5% ee: J. Am. Chem. Soc., 117, 8277 (1995).
• Undergoes rhodium-catalyzed addition with potassium organotrifluoroborates to give substituted alanine derivatives: Eur. J. Org. Chem., 69 (2004). In the presence of a Rh-BINAP catalyst, chiral amino acid derivaitives are formed with good ee: Angew. Chem. Int. Ed., 43, 719 (2004).