ethyl 2-(diethoxyphosphoryl)propanoate

• ChemBase编号: 91243
• 分子式: C9H19O5P
• 平均质量: 238.217921
• 单一同位素质量: 238.09701034
• SMILES: P(=O)(OCC)(OCC)C(C)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)C
• InChI: InChI=1S/C9H19O5P/c1-5-12-9(10)8(4)15(11,13-6-2)14-7-3/h8H,5-7H2,1-4H3
• InChIKey: BVSRWCMAJISCTD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 2-(diethoxyphosphoryl)propanoate
• IUPAC传统名: ethyl 2-(diethoxyphosphoryl)propanoate
• 别名: 2-膦酰丙酸三乙酯; 2-膦酰丙酸三乙脂; Triethyl 2-phosphonopropionate; Ethyl 2-(diethoxyphosphoryl)propanoate; Diethyl [1-(ethoxycarbonyl)ethyl]phosphonate 97%; ethyl 2-(diethoxyphosphoryl)propanoate; Diethyl ethoxycarbonylethyl-phosphonate; TRIETHYL 2-PHOSPHONOPROPIONATE; 2-(Diethoxyphosphoryl)propionic acid ethyl ester; Triethyl 2-phosphonopropionate; Diethyl 1-(ethoxycarbonyl)ethanephosphonate; 2-Phosphonopropionic acid triethyl ester

登记号

• CAS号: 3699-66-9
• EC号: 223-033-4
• MDL号: MFCD00009159
• Beilstein号: 1786994
• PubChem SID: 162077947; 24850353
• PubChem CID: 107155

理论计算性质

• Acid pKa: 18.457832
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.1510886
• LogD (pH = 7.4): 1.1510886
• Log P: 1.1510886
• 摩尔折射率: 56.1074 cm^3
• 极化性: 22.862322 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

• 沸点: 102-104°C; 143-144 °C/12 mmHg(lit.); 143-144°C/12mm
• 闪点: 192.2 °F; 88°C; 88°C(190°F); 89 °C
• 密度: 1.111; 1.111 g/mL at 25 °C(lit.)
• 折射率: 1.431; 1.4320; n20/D 1.431(lit.)
• 疏水性(logP): 1.161

安全信息

• 保存条件: 0°C
• 保存注意事项: Irritant
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: R:36/37/38
• 安全公开号: S:20-25-26-37/39
• TSCA收录: 否
• 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, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

产品相关信息

• 纯度: 95%; 98%
• 线性分子式: (C2H5O)2P(O)CH(CH3)CO2C2H5

详细说明

MP Biomedicals - 02157017

(Diethyl ethoxycarbonylethyl-phosphonate)

Sigma Aldrich - 174653

包装
10, 50 g in glass bottle
Application
Reactant involved in:
• Intramolecular conjugate addition for the synthesis of floresolide B1
• Chemoenzymatic one-pot synthesis of γ-butyrolactones2
• Enantioselective synthesis of spiroindane di-Me acetic acid via asymmetric hydrogenation3
• Stereoselective intramolecular Diels-Alder reactions4,5
• Horner-Wadsworth-Emmons reactions6
该 Wittig-Horner 试剂可与各种醛和酮发生缩合反应形成丙烯酸酯。

参考文献

• Wadsworth-Emmons precursor of methacrylic esters (see Triethyl phosphonoacetate, A14120 and Appendix 1). Lithiation followed by acylation with perfluoroalkanoic anhydrides gives a perfluoroacyl intermediate which, with an organolithium reagent, leads stereoselectively to a trifluoroalkylated ɑ?-unsaturated ester: J. Fluorine Chem., 89, 141 (1998):