methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate

• ChemBase编号: 67362
• 分子式: C21H19O2P
• 平均质量: 334.348121
• 单一同位素质量: 334.11226648
• SMILES: P(=CC(=O)OC)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3
• InChIKey: NTNUDYROPUKXNA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; methyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• IUPAC传统名: methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; methyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• 别名: (三苯基膦烯)乙酸甲酯; 甲氧羰基亚甲基三苯基正磷; 甲氧甲酰基亚甲基三苯基膦; (甲氧基羰基亚甲基)三苯基膦烷; Carbomethoxymethylene triphenylphosphorane; (Methoxycarbonylmethylene)triphenylphosphorane; Methyl (triphenylphosphoranylidene)acetate 98%; (Carbomethoxymethylene)triphenylphosphorane; Methyl (triphenylphosphoranylidene)acetate; Methyl (triphenylphosphoranylidene)acetate; (Methoxycarbonylmethylene)triphenylphosphorane; Methyl(triphenylphosphoranylidene)acetate

登记号

• CAS号: 2605-67-6
• EC号: 220-018-4
• MDL号: MFCD00008455
• Beilstein号: 618430
• PubChem SID: 24849709; 162033097
• PubChem CID: 17453

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 5.8956
• LogD (pH = 7.4): 5.8956
• Log P: 5.8956
• 摩尔折射率: 98.4491 cm^3
• 极化性: 38.770615 Å^3
• 极化表面积: 26.3 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform
• 外观: Off-White Solid
• 熔点: 159-162°C; 165-169°C; 168-172 °C; 168-172 °C(lit.)

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Air Sensitive; IRRITANT; Irritant
• 德国WGK号: 3
• TSCA收录: false; 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97.0% (CH); 95+%; 98%
• 级别: purum
• 线性分子式: (C6H5)3P=CHCO2CH3

详细说明

Sigma Aldrich - 157929

Application
Wittig 试剂，用于醛的二碳同素化反应生成 α,β-不饱和酯。1在三乙胺存在的条件下，也可用于与重氮基乙酸甲酯反应高效合成吡唑。2
包装
25, 100 g in poly bottle
5 g in glass bottle

参考文献

• For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):
  
• Review of phosphacumulene ylides: Angew. Chem. Int. Ed.,16, 349 (1977).
• Stable ylide which undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. See also (Ethoxycarbonylmethylene)triphenylphosphorane, A12896 and Appendix 1. For a detailed study of the reaction with benzaldehyde, see J. Org. Chem., 59, 1126 (1994). For use of high pressure to increase the yield and trans-selectivity of reaction with aromatic aldehydes, see: Liebigs Ann. Chem., 2135 (1983).
• Strong base, for example Na bis(TMS)amide, brings about elimination of methanol, giving ketenylidenetriphenylphosphorane, which reacts with ɑ-hydroxy-ketones, e.g. in the steroid series, to give butenolides, by acylation and Wittig cyclization: Chem. Ber., 113, 2038 (1980):