dimethyl (2-oxopropyl)phosphonate

• ChemBase编号: 74987
• 分子式: C5H11O4P
• 平均质量: 166.112201
• 单一同位素质量: 166.03949546
• SMILES: P(=O)(OC)(CC(=O)C)OC
• Canonical SMILES: COP(=O)(CC(=O)C)OC
• InChI: InChI=1S/C5H11O4P/c1-5(6)4-10(7,8-2)9-3/h4H2,1-3H3
• InChIKey: UOWIYNWMROWVDG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl (2-oxopropyl)phosphonate
• IUPAC传统名: dimethyl 2-oxopropylphosphonate
• 别名: 丙酮基磷酸二甲酯; 2-氧代丙基膦酸二甲酯; 丙酮基膦酸二甲酯; Dimethyl (acetylmethyl)phosphonate; (Dimethoxyphosphoryl)acetone; Dimethyl (2-oxoprop-1-yl)phosphonate 97+%; Dimethyl acetonylphosphonate; Dimethyl 2-oxopropylphosphonate; dimethyl (2-oxopropyl)phosphonate; DIMETHYL (2-OXOPROPYL)-PHOSPHONATE; Acetylmethylphosphonic acid dimethyl ester; Dimethyl acetylmethylphosphonate

登记号

• CAS号: 4202-14-6
• EC号: 224-110-5
• MDL号: MFCD00008769
• Beilstein号: 1766218
• PubChem SID: 162039905; 24886902; 24850888
• PubChem CID: 77872

理论计算性质

• Acid pKa: 15.5211315
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.08418241
• LogD (pH = 7.4): -0.08418242
• Log P: -0.08418241
• 摩尔折射率: 36.1497 cm^3
• 极化性: 14.842041 Å^3
• 极化表面积: 52.6 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 121-123°C/11mm; 76-79 °C/3 mmHg(lit.); 76-79°C @ 3 mm Hg; 76-79°C/3mm
• 闪点: 199.4 °F; 93 °C; 93.3°C; 93°C(199°F)
• 密度: 1.202; 1.202 g/ml; 1.202 g/mL at 25 °C(lit.)
• 折射率: 1.439; 1.4390; n20/D 1.439(lit.)
• 疏水性(logP): -0.84

安全信息

• 保存条件: 2-8°C
• 保存注意事项: Irritant
• 德国WGK号: 3
• 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, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (GC); 95%; 95+%; 97%; 98%
• 级别: technical
• 线性分子式: CH3COCH2P(O)(OCH3)2

详细说明

MP Biomedicals - 02157834

Purity: 95%

Sigma Aldrich - 180696

Application
与甲苯磺酰叠氮化物共同用于醛的一锅法炔基化反应的试剂。1,2
包装
5, 25 g in glass bottle

Sigma Aldrich - 75948

Other Notes
用于醛的丙酮酸化反应的 Wittig-Horner 试剂；得到高 E/Z 比（CH3CN 中的 DBU、LiCl）的最佳条件1,2,3；通过二价阴离子的 γ-烷基化反应合成 β-酮基膦酸酯4

参考文献

• For use of ?-ketophosphonates in an annulation sequence for building a cyclohexadienone ring onto a cyclic ketone, see: Synthesis, 855 (1982):
  
• Successive treatment with NaH and n-BuLi gives the dianion which can be alkylated or acylated on the terminal position: see. e.g.: Synth. Commun., 22, 219 (1992); J. Chem. Soc., Perkin 1, 2259 (1998).
• Horner-Wadsworth-Emmons precursor of ɑ?-unsaturated ketones.