methyl 2-(dimethoxyphosphoryl)acetate

• ChemBase编号: 112025
• 分子式: C5H11O5P
• 平均质量: 182.111601
• 单一同位素质量: 182.03441008
• SMILES: COC(=O)CP(=O)(OC)OC
• Canonical SMILES: COC(=O)CP(=O)(OC)OC
• InChI: InChI=1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
• InChIKey: SIGOIUCRXKUEIG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 2-(dimethoxyphosphoryl)acetate
• IUPAC传统名: methyl 2-(dimethoxyphosphoryl)acetate
• 别名: 三甲基膦酰基乙酸酯; 磷酸乙酸三甲酯; (Carboxymethyl)phosphonic acid trimethyl ester; NSC 84262; Trimethyl phosphonoacetate; TRIMETHYL PHOSPHONOACETATE; Dimethyl methoxycarbonylmethylphosphonate; Phosphonoacetic acid trimethyl ester; methyl 2-(dimethoxyphosphoryl)acetate

登记号

• CAS号: 5927-18-4
• EC号: 227-663-0
• MDL号: MFCD00008452
• Beilstein号: 1865177
• PubChem SID: 24887467; 24900489; 162097263
• PubChem CID: 80029

理论计算性质

• Acid pKa: 18.555302
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.42275944
• LogD (pH = 7.4): -0.42275944
• Log P: -0.42275944
• 摩尔折射率: 37.3677 cm^3
• 极化性: 15.617066 Å^3
• 极化表面积: 61.83 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 118 °C/0.85 mmHg(lit.); 119-120°C/1mm; 265-268 °C(lit.)
• 闪点: 113 °C; 235.4 °F; 70°C(158°F)
• 密度: 1.125 g/mL at 25 °C(lit.); 1.263
• 折射率: 1.4370; n20/D 1.437; n20/D 1.437(lit.)

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 9-36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319-H335-H227
• GHS警示性声明: P210-P305+P351+P338-P302+P352-P321-P405-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: ≥98.0% (GC); 98%
• 级别: purum
• 线性分子式: (CH3O)2P(O)CH2CO2CH3

详细说明

MP Biomedicals - 05222246

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T79758

包装
25, 100 g in glass bottle
Application
Reactant involved in:
• Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core1
• Organocatalytic oxa-Michael reactions2
• Prenylation and geranylation of oxindoles3
• Intramolecular Horner-Wadsworth-Emmons reactions4,5
• Olefin cross-metathesis / heterocyclization6

Sigma Aldrich - 79527

Application
Reactant involved in:
• Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core1
• Organocatalytic oxa-Michael reactions2
• Prenylation and geranylation of oxindoles3
• Intramolecular Horner-Wadsworth-Emmons reactions4,5
• Olefin cross-metathesis / heterocyclization6

参考文献

• Horner-Wadsworth-Emmons olefination (see Appendix 1) with aldehydes and ketones gives acrylic esters, cf Triethyl phosphonoacetate, A14120. In general, the (E):(Z) ratio of the resulting alkene increases as the counter-ion becomes smaller (K, Na, Li) and as the temperature increases. See, e.g.: J. Org. Chem., 55, 3386 (1990). Reaction with ɑ-hydroxy ketones provides a simple route to butenolides: Tetrahedron Lett., 36, 2839 (1995):