ethyl 2-(diethoxyphosphoryl)acetate

• ChemBase编号: 74926
• 分子式: C8H17O5P
• 平均质量: 224.191341
• 单一同位素质量: 224.08136027
• SMILES: P(=O)(OCC)(CC(=O)OCC)OCC
• Canonical SMILES: CCOC(=O)CP(=O)(OCC)OCC
• InChI: InChI=1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3
• InChIKey: GGUBFICZYGKNTD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 2-(diethoxyphosphoryl)acetate
• IUPAC传统名: triethyl phosphonoacetate
• 别名: 乙氧基羰酰甲基膦酸二乙酯; 羧甲基膦酸三乙酯; 膦酰基乙酸三乙酯; 膦酰乙酸三乙酯; Triethyl phosphonoacetate; Ethyl (diethoxyphosphoryl)acetate; Diethyl (ethoxycarbonylmethyl)phosphonate; (Diethoxyphosphinyl)acetic acid ethyl ester; NSC 13898; NSC 16128; Diethyl ethoxycarbonylmethylphosphonate; Triethyl carboxymethylphosphonate; Triethyl phosphonoacetate; 2-(Diethoxyphosphinyl)acetic Acid Ethyl Ester; Carbethoxymethyldiethyl Phosphonate; Phosphonoacetic acid triethyl ester; Ethyl 2-(diethoxyphosphoryl)acetate; Diethyl ethoxycarbonylmethyl-phosphonate; TRIETHYL PHOSPHONOACETATE

登记号

• CAS号: 867-13-0
• EC号: 212-757-6
• MDL号: MFCD00009177
• Beilstein号: 1343714
• PubChem SID: 24887466; 162039844; 24900348
• PubChem CID: 13345
• 维基百科标题: Triethyl_phosphonoacetate

理论计算性质

• Acid pKa: 17.777735
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.6265928
• LogD (pH = 7.4): 0.6265928
• Log P: 0.6265928
• 摩尔折射率: 51.6135 cm^3
• 极化性: 21.043863 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; Ethyl Acetate
• 外观: Colorless, Clear liquid
• 熔点: -24°C; -24°C
• 沸点: 142-145 °C at 9 mmHg; 142-145 °C/9 mmHg(lit.); 260-262°C; 260-262°C
• 闪点: 105 °C; 105°C; 165°C(329°F); 221 °F
• 密度: 1.125; 1.13; 1.13 g/mL at 25 °C(lit.)
• 折射率: 1.431; 1.4310; n20/D 1.431(lit.); n20/D 1.432

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: Irritant
• RTECS编号: AG9800000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 3082
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 36/38; 51/53
• 安全公开号: 23-26-37; 61
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS危险声明: H315-H319
• GHS警示性声明: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• 个人保护装置: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3082 9/PG 3

产品相关信息

• 纯度: >95%; ≥97.0% (GC); 95+%; 98%; 98+%
• 级别: purum
• 线性分子式: (C2H5O)2P(O)CH2CO2C2H5

详细说明

MP Biomedicals - 02157016

Purity: >95%

Sigma Aldrich - T61301

Application
Horner-Emmons-Wadsworth 试剂，近来用于通过 (S)-环氧丙烷合成手性 2-甲基环丙烷羧酸。7
Reactant involved in:
• Horner-Wadsworth-Emmons reactions1,2
• Intramolecular Heck-type cyclization and isomerizations3
• Tsuji-Trost type reactions4
• Intramolecular aryne-ene reactions5
• Synthesis of aldehydes6
包装
100 g in poly bottle
25 g in glass bottle

Sigma Aldrich - 79525

Other Notes
Horner-Wittig 试剂，综述7,8；可改善酯的 C2 同系化反应生成 α,β-不饱和酯的过程9；合成 α-(羟甲基)丙烯酸酯10
Application
Reactant involved in:
• Horner-Wadsworth-Emmons reactions1,2
• Intramolecular Heck-type cyclization and isomerizations3
• Tsuji-Trost type reactions4
• Intramolecular aryne-ene reactions5
• Synthesis of aldehydes6

Toronto Research Chemicals - T777000

Reagent used for Horner-Emmons modification.

参考文献

• Hediger, M., et al.: Bioorg. Med. Chem., 12, 4995 (2004)
• Kim, J., et al.: Nat., 452, 239 (2004)
• Base-catalyzed aldol, Cannizzaro and saponification reactions can be minimized, by the use of, e.g.: K₂CO₃: Synthesis, 300 (1983); Tetrahedron Lett., 26, 53 (1985); F^-: Tetrahedron Lett., 21, 2161 (1980); N-ethyldiisopropylamine + LiCl: Tetrahedron Lett., 25, 2183 (1984); Et₃N + Li halides: J. Org. Chem., 50, 2624 (1985).
• Reaction with aqueous formaldehyde does not lead to the "expected" Wadsworth-Emmons product, but to ethyl ɑ-(hydroxymethyl)acrylate, a precursor of the synthetically useful ethyl ɑ-bromomethylacrylate, by condensation with the initially-formed "aldol" product: Org. Synth. Coll., 8, 265 (1993).
• Wadsworth-Emmons (Horner) reaction with aldehydes and ketones gives acrylic esters. See, e.g.: Org. Synth. Coll., 5, 509, 547 (1973), and Appendix 1.