1,3-diethyl 2-oxopropanedioate

• ChemBase编号: 8029
• 分子式: C7H10O5
• 平均质量: 174.1513
• 单一同位素质量: 174.05282342
• SMILES: CCOC(=O)C(=O)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(=O)C(=O)OCC
• InChI: InChI=1S/C7H10O5/c1-3-11-6(9)5(8)7(10)12-4-2/h3-4H2,1-2H3
• InChIKey: DBKKFIIYQGGHJO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,3-diethyl 2-oxopropanedioate
• IUPAC传统名: 1,3-diethyl 2-oxopropanedioate
• 别名: 2-氧代丙二酸二乙酯; 二乙基双乙烯酯; 酮基丙二酸二乙酯; 酮基丙二酸二乙酯; 丙酮二酸二乙酯; Diethyl 2-oxopropane-1,3-dioate; Diethyl ketomalonate; Diethyl 2-oxomalonate 97%; Diethyl ketomalonate; Diethyl mesoxalate; Ketomalonic acid diethyl ester; Diethyl ketomalonate; Diethyl mesoxalate; Diethyl oxomalonate; Diethyl mesoxalate

登记号

• CAS号: 609-09-6
• EC号: 210-176-2
• MDL号: MFCD00009121
• Beilstein号: 971873
• 默克索引号: 145913
• PubChem SID: 160971336; 24894323; 24883047
• PubChem CID: 69105

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.4975388
• LogD (pH = 7.4): 1.4975388
• Log P: 1.4975388
• 摩尔折射率: 38.82 cm^3
• 极化性: 15.412765 Å^3
• 极化表面积: 69.67 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: ca -70°C
• 沸点: 208-210 °C(lit.); 208-210°C; 208-210°C; 95-98 °C/12 mmHg(lit.); 96-98°C
• 闪点: >110°C(230°F); 113 °C; 235.4 °F
• 密度: 0.927; 1.128 g/mL at 20 °C(lit.); 1.142; 1.142 g/mL at 25 °C(lit.)
• 折射率: 1.4150; 1.4175; n20/D 1.415; n20/D 1.415(lit.)

安全信息

• 保存注意事项: IRRITANT, MOISTURE SENSITIVE; Irritant/Moisture Sensitive; Moisture Sensitive
• 德国WGK号: 3
• TSCA收录: true; 是
• 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: ≥96.0% (GC); 95%; 95+%
• 级别: purum
• Appearance: green-yellow liquid
• 线性分子式: CO(CO2C2H5)2; CO(COOC2H5)2

详细说明

MP Biomedicals - 05215003

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D97401

包装
5, 25 g in glass bottle
Application
用于经 Wittig 和 Aza-Wittig 反应分别合成三唑类1和 2-氮杂二烯的试剂2。

Sigma Aldrich - 63970

Other Notes
与烯烃反应生成烯丙基羧酸1；DA 环加成反应生成杂环化合物2,3

参考文献

• The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ?-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):
  
• Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ?-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):
  
• For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).
• Thus, the reagent could be regarded as a CO₂ equivalent in both the above sequences.
• Undergoes the Baylis-Hillman reaction in which a carbanionic species, generated by the reversible addition of 1,4-Diazabicyclo[2.2.2]octane, A14003, to a Michael acceptor, adds to the carbonyl group: Synth. Commun., 19, 2461 (1989).
• Reacts with activated arenes under Friedel-Crafts conditions, or with aryllithium or Grignard derivatives, to give aryl hydroxymalonates, hydrolysis and decarboxylation of which gives substituted mandelic acids: Org. Synth. Coll., 3, 326 (1955). Alternatively, they may be transformed reductively to arylmalonates and hence to ester enolates: J. Org. Chem., 47, 4692 (1982).