1,3-diethyl 2-(ethoxymethylidene)propanedioate

• ChemBase编号: 122910
• 分子式: C10H16O5
• 平均质量: 216.23104
• 单一同位素质量: 216.09977361
• SMILES: C(=COCC)(C(=O)OCC)C(=O)OCC
• Canonical SMILES: CCOC=C(C(=O)OCC)C(=O)OCC
• InChI: InChI=1S/C10H16O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h7H,4-6H2,1-3H3
• InChIKey: LTMHNWPUDSTBKD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• IUPAC传统名: 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• 别名: 乙氧基亚甲基丙二酸二乙酯; 乙氧基甲叉丙二酸二乙酯; 乙氧亚甲基丙二酸二乙酯; Diethyl ethoxymethylenemalonate; diethyl 2-(ethoxymethylene)malonate; Diethyl (ethoxymethylene)malonate; 2-(Ethoxymethylene)propanedioic Acid 1,3-Diethyl Ester; (Ethoxymethylene)malonic Acid Diethyl Ester; (Ethoxymethylene)propanedioic Acid Diethyl Ester; Diethyl[(ethyloxy)methylidene]propanedioate; Ethyl 3-Ethoxy-2-(ethoxymethylene)-3-oxopropanoate; NSC 62117; NSC 9068; Diethyl Ethoxymethylidenemalonate; Diethyl EthoxyMethyleneMalonate; Ethoxymethylenemalonic acid diethyl ester; Ethoxymethylenepropanedioic acid diethyl ester

登记号

• CAS号: 87-13-8
• EC号: 201-725-7
• MDL号: MFCD00009148
• Beilstein号: 880058
• PubChem SID: 24894294; 24845377; 162217263
• PubChem CID: 6871

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.471484
• LogD (pH = 7.4): 1.471484
• Log P: 1.471484
• 摩尔折射率: 53.8786 cm^3
• 极化性: 21.211697 Å^3
• 极化表面积: 61.83 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Dichloromethane; Methanol
• 外观: Colourless Liquid
• 熔点: -33°C
• 沸点: 136-139°C/10mm; 279-281 °C(lit.); 279-283 °C(lit.)
• 闪点: 144 °C; 144°C(291°F); 291.2 °F
• 密度: 1.07 g/mL at 25 °C(lit.); 1.080; 1.080 g/mL at 20 °C(lit.)
• 折射率: 1.4620; n20/D 1.462(lit.); n20/D 1.463

安全信息

• 保存条件: Refrigerator
• RTECS编号: OO1100000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22-36/37/38; 22-36/38-42/43
• 安全公开号: 23-24-26-36/37-45; 26-36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335; H334-H315-H319-H317-H303
• GHS警示性声明: P261-P305 + P351 + P338; P285-P261-P305+P351+P338-P302+P352-P321-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: ≥99.0% (GC); 95+%; 97%; 98+%; 99%
• 级别: purum
• 线性分子式: C2H5OCH=C(COOC2H5)2

详细说明

Sigma Aldrich - D94208

包装
5, 100, 500 g in glass bottle

Toronto Research Chemicals - D444300

Intermediate in the production of Flumequine

参考文献

• Sato, M., et al.: J. Med. Chem., 52, 4869 (2009)
• Can be converted to the unstable diethyl methylenemalonate by catalytic reduction and elimination of ethanol on distillation, see: Org. Synth. Coll., 4, 298 (1963).
• Stable equivalent of the ɑ-formylmalonate, valuable synthetic building block, particularly in heterocyclic syntheses. Review: Adv. Het. Chem., 54, (1992).
• Has been used for the protection of the amino group of ɑ-amino acids, allowing clean esterification by O-alkylation. The protecting group can be removed using bromine in chloroform: Synthesis, 544 (1989):
  
• For N-protection of aminoglycosides prior to O-acetylation, see: J. Carbohydr. Chem., 14, 1133 (1995). Chlorine in chloroform at 0^oC was used for deprotection.