1,4-diethyl (2S,3S)-2,3-dihydroxybutanedioate

• ChemBase编号: 127008
• 分子式: C8H14O6
• 平均质量: 206.19316
• 单一同位素质量: 206.07903817
• SMILES: O=C(OCC)[C@@H](O)[C@H](O)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H]([C@@H](C(=O)OCC)O)O
• InChI: InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1
• InChIKey: YSAVZVORKRDODB-WDSKDSINSA-N

名称和登记号

名称

• IUPAC标准名: 1,4-diethyl (2S,3S)-2,3-dihydroxybutanedioate
• IUPAC传统名: diethyl tartrate
• 别名: D-(-)-酒石酸二乙酯; L-(+)-酒石酸二乙酯; Diethyl tartrate; D-(-)-Tartaric acid diethyl ester; (-)-Diethyl D-tartrate; L-Tartaric acid diethyl ester; (+)-Diethyl L-tartrate; D-Tartaric acid diethyl ester; (2S,3S)-Diethyl 2,3-dihydroxysuccinate

登记号

• CAS号: 13811-71-7; 87-91-2
• EC号: 201-783-3; 237-458-8
• MDL号: MFCD00009143; MFCD00064451
• Beilstein号: 1727145; 1727143
• 默克索引号: 143855
• PubChem SID: 162221331; 24852814
• PubChem CID: 62333; 117410
• Chemspider ID: 104927
• 维基百科标题: Diethyl_tartrate

理论计算性质

• Acid pKa: 11.187077
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -0.82339674
• LogD (pH = 7.4): -0.8234667
• Log P: -0.82339585
• 摩尔折射率: 45.2488 cm^3
• 极化性: 18.454937 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: low in water
• 外观: colourless
• 熔点: 17°C
• 沸点: 162 °C/19 mmHg(lit.); 280 °C; 280°C
• 闪点: 199.4 °F; 93 °C; 93°C(199°F)
• 密度: 1.204 g/mL; 1.205; 1.205 g/mL at 20 °C(lit.)
• 折射率: 1.4460; n20/D 1.446(lit.); n20/D 1.447
• 比旋光度: [α]20/D -26.5±1°, c = 1% in H2O; [α]23/D -8.5°, neat; +27 (c=1 in water); -26.5 (c=1 in water)

安全信息

• 德国WGK号: 3
• 安全公开号: 15
• TSCA收录: 否; 是
• GHS危险声明: H227
• GHS警示性声明: P210-P280-P370+P378A-P403+P235-P501A
• 个人保护装置: Eyeshields, Gloves

产品相关信息

• 纯度: ≥99%; ≥99.0% (sum of enantiomers, GC); 98%; 99%
• 级别: puriss.
• 光学纯度: ee: ≥99% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• 线性分子式: HO2CCCH(OH)CH(OH)CO2H

详细说明

Sigma Aldrich - 213969

包装
5, 25, 500 g in glass bottle

参考文献

• For use as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, see tert-Butyl hydroperoxide, A13926. For Sharpless-type enantioselective oxidation of sulfides to sulfoxides, see: Org. Synth. Coll., 8, 464 (1993).
• For use as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction, see: Chem. Lett., 61 (1992). For a review of the use of tartrate esters as chiral auxiliaries, e.g. in the Simmons-Smith reaction and in 1,3-dipolar cycloaddition reactions, see: Synlett, 1075 (2003).