triethyl methanetricarboxylate

• ChemBase编号: 148386
• 分子式: C10H16O6
• 平均质量: 232.23044
• 单一同位素质量: 232.09468823
• SMILES: CCOC(=O)C(C(=O)OCC)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(C(=O)OCC)C(=O)OCC
• InChI: InChI=1S/C10H16O6/c1-4-14-8(11)7(9(12)15-5-2)10(13)16-6-3/h7H,4-6H2,1-3H3
• InChIKey: AGZPNUZBDCYTBB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: triethyl methanetricarboxylate
• IUPAC传统名: triethyl methanetricarboxylate
• 别名: 甲烷三羧酸三乙酯; Triethyl methanetricarboxylate; Methanetricarboxylic acid triethyl ester; Tris(carboethoxy)methane; N-triethylmethanetricarboxylate; Triethyl methanetricarboxylate

登记号

• CAS号: 6279-86-3
• EC号: 228-477-2
• MDL号: MFCD00009150
• Beilstein号: 1793645
• PubChem SID: 162242562; 24900338; 24883241
• PubChem CID: 80471

理论计算性质

• Acid pKa: 6.862826
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.8939805
• LogD (pH = 7.4): 0.31972072
• Log P: 0.91166764
• 摩尔折射率: 53.8326 cm^3
• 极化性: 21.612305 Å^3
• 极化表面积: 78.9 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 25-26 °C(lit.); 26-29°C; 28 - 29°C
• 沸点: 253 °C(lit.); 253°C
• 闪点: >110°C(230°F); 113 °C; 235.4 °F
• 密度: 1.095; 1.095 g/mL at 25 °C(lit.)
• 折射率: 1.4255; n20/D 1.424(lit.); n20/D 1.426
• 疏水性(logP): 1.543

安全信息

• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

产品相关信息

• 纯度: ≥98.0% (GC); 95%; 97%; 98%
• 级别: purum
• 线性分子式: CH(CO2C2H5)3

详细说明

Sigma Aldrich - T60208

包装
5, 25 g in glass bottle

Sigma Aldrich - 64300

Other Notes
可抑制二烷基化并消除副反应的简便丙二酸酯衍生物1,2,3；综述4

参考文献

• Methanetricarboxylates have been used as "blocked" malonic esters, restricting reaction with alkyl halides to monoalkylation. The unwanted carboxyl group can be removed by treatment with Na alkoxide, LDA or BCl₃: J. Org. Chem., 44, 3492 (1979). Adds to Michael acceptors under phase-transfer conditions, providing a useful 2-carbon chain extension method: Synthesis, 1125 (1990):
  
• The tricarboxylate also undergoes free-radical addition to the terminal position of alkenes: Angew. Chem. Int. Ed., 5, 586 (1966). Arylation with electron-rich aromatics is promoted by Mn(III): Synthesis, 567 (1991).
• Under similar conditions, diethyl malonate gives only 36% yield.