Efficient syntheses of (alpha-fluoropropargyl)phosphonate esters
Efficient syntheses of (alpha-fluoropropargyl)phosphonate esters
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DOI：
10.1021/jo9602027
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发表时间：
1996-07-26
影响因子：
3.6
通讯作者：
Hammond, GB
中科院分区：
文献类型：
--
作者：
Benayoud, F;deMendonca, DJ;Hammond, GB
磷酸盐的r -碳。2 .由于由此产生的氟甲基膦酸盐衍生物（即母体磷酸盐）具有等构和等电子特性，氟增加了磷酸盐模拟物的有效性。许多关于r -氟烷膦酸盐1的合成报道强调了氟取代在膦酸盐中的重要性，其中大多数是利用（氟乙烯）膦酸二乙酯-(+ M-CHF-P （O)(OEt) 2）作为含氟合成物。3值得注意的例外是通过亲电氟化合成r -氟烷膦酸盐，4和(二乙基酰胺硫三氟化（DAST）促进取代（r -羟基苄基）膦酸盐。最近，某些环和无环不饱和膦酸盐衍生物（如26）具有抗病毒和抗肿瘤活性的发现引发了人们对合成γ-不饱和烯膦酸盐的兴趣。这样推测是合理的
R-carbon of phosphonates. 2 Fluorine increases the effectiveness of phosphate mimetics due to the isosteric and isoelectronic character of the resulting fluoromethylenephosphonate derivative, viz. a viz. the parent phosphate. The importance of fluorine substitution in phosphonates has been underscored by numerous reported syntheses of R-fluoroalkanephosphonates 1, the majority of which utilized the diethyl ester of (fluoromethylene) phosphonate-(+ M-CHF-P (O)(OEt) 2) as a fluorine-containing synthon. 3 Notable exceptions are the synthesis of R-fluoroalkanephosphonates via electrophilic fluorination, 4 and (diethylamidosulfur trifluoride (DAST) promoted replacement of (R-hydroxybenzyl) phosphonates. 5 Recently, the discovery of antiviral and antitumor activity in certain cyclic and acyclic unsaturated phosphonate derivatives such as 26 has sparked interest in the synthesis of, γ-unsaturated alkenephosphonates. It is plausible to speculate that