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CAS RN: 88738-78-7 | 產品號碼: B1714
Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate
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| 產品號碼 | B1714 |
| 純度/分析方法 | >95.0%(GC) |
| 分子式 / 分子量 | C__7H__9F__6O__5P = 318.11 |
| 外觀與形狀（20°C） | Liquid |
| 儲存條件 | Room Temperature (Recommended in a cool and dark place, <15°C) |
| 儲存在惰性氣體下 | Store under inert gas |
| 應避免的情況 | Air Sensitive |
| 包裝和容器 | 1G-Plastic Bottle with Glass Insert （閲覽圖片） |
| CAS RN | 88738-78-7 |
| Reaxys-RN | 3594044 |
| PubChem Substance ID | 87564613 |
| SDBS (AIST Spectral DB) | 21981 |
| MDL編號 | MFCD00009901 |
產品規格
| Appearance | Colorless to Light yellow clear liquid |
| Purity(GC) | min. 95.0 % |
性質
| 比重 | 1.50 |
| 折射率 | 1.37 |
GHS
| 圖形表示 |
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| 信號詞 | Warning |
| 危險性說明 | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| 防範說明 | P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. |
相關法規
運輸資料
| HS編碼* | 2931.59-000 |
Application
TCI Practical Example: Z-Stereoselective Horner-Wadsworth-Emmons Olefination via Still-Gennari Method
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Used Chemicals
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Procedure
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Potassium tert-butoxide (236 mg, 2.1 mmol, 2.1 eq.) in dry THF (5 mL) was added dropwise to the solution of p-tolualdehyde (120 mg, 1.0 mmol), bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (636 mg, 2.0 mmol, 2.0 eq.) and 18-crown-6-ether (793 mg, 3.0 mmol, 3.0 eq.) in dry THF (5 mL) at -78 °C. The mixture was stirred for 2 hours. Then the mixture was stirred at r.t. for overnight and quenched with water (15 mL). The aqueous layer was extracted with ethyl acetate (15 mL x 3) and the combined organic layer was washed with 2 mol/L HCl aq. (10 mL), sat. NaHCO3 aq. (10 mL), and brine (10 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, toluene:diethyl ether = 40:1) to give 1 as a pale yellow liquid (138 mg, 78% yield, E:Z = 1:15.5).
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Experimenter’s Comments
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The reaction mixture was monitored by UPLC.
The ratio of E form and Z form was estimated from NMR.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3);
1-Z: δ 7.53 (d, J = 7.6 Hz, 2H), 7.17 (d, J = 7.6 Hz, 2H), 6.91 (d, J = 12.8 Hz, 1H), 5.90 (d, J = 12.8 Hz, 1H), 3.72 (s, 3H), 2.36 (s, 3H).
1-E: δ 7.67 (d, J = 16.0 Hz, 1H), 7.42 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 8.4 Hz, 2H), 6.40 (d, J = 16.0 Hz, 1H), 3.80 (s, 3H), 2.37 (s, 3H). -
Lead Reference
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- Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.
Application
Z-Selective Horner-Emmons Olefination
References
Direct synthesis of Z-unsaturated esters
S. J. Danishefsky, M. P. DeNinno, J. Org. Chem. 1986, 51, 2615.
W. R. Roush, A. D. Palkowitz, ibid. 1989, 54, 3009.
α-Alkylation of reagent B1714 and olefination
J. C. Medina, R. Guajardo, K. S. Kyler, J. Am. Chem. Soc. 1989, 111, 2310.
考研文獻
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