【结 构 式】 |
【分子编号】49035 【品名】(Z)-10-(tert-butoxy)-1,1,1-trifluoro-6,6-dimethyl-2-(trifluoromethyl)-3-decen-2-ol 【CA登记号】 |
【 分 子 式 】C17H28F6O2 【 分 子 量 】378.3985392 【元素组成】C 53.96% H 7.46% F 30.12% O 8.46% |
合成路线1
该中间体在本合成路线中的序号:(VI)Synthesis of aldehyde intermediate (IX): The condensation of 1-tert-butoxy-4-chlorobutane (I) with 4-methyl-3-penten-2-one (II) by means of Mg in hot THF gives the 2-octanone (III), which is condensed with hexafluoroacetone (IV) by means of diethyl chlorophosphate and LDA in THF to yield the fluorinated alkynol (V). Hydrogenation of the triple bond of (V) with H2 and Lindlar catalyst affords the cis-alkene (VI), which is deprotected with sulfuric acid to provide the fluorinated diol (VII). Finally, the primary alcohol of (VII) is oxidized to the corresponding aldehyde (VIII) with NaOCl and tempo, which is silylated with Tes-Cl and TEA to afford the desired intermediate (IX).
【1】 Wirz, B.; Hilpert, H.; Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D-3 derivative. Tetrahedron 2001, 57, 4, 681. |
【2】 Hilpert, H.; Wirz, B. (F. Hoffmann-La Roche AG); New process for the preparation of retiferol derivs.. EP 1094060 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 49032 | tert-butyl 4-chlorobutyl ether; 1-(tert-butoxy)-4-chlorobutane | C8H17ClO | 详情 | 详情 | |
(II) | 42266 | 4-methyl-3-penten-2-one | 141-79-7 | C6H10O | 详情 | 详情 |
(III) | 49033 | 8-(tert-butoxy)-4,4-dimethyl-2-octanone | C14H28O2 | 详情 | 详情 | |
(IV) | 44260 | 1,1,1,3,3,3-hexafluoroacetone | 684-16-2 | C3F6O | 详情 | 详情 |
(V) | 49034 | 10-(tert-butoxy)-1,1,1-trifluoro-6,6-dimethyl-2-(trifluoromethyl)-3-decyn-2-ol | C17H26F6O2 | 详情 | 详情 | |
(VI) | 49035 | (Z)-10-(tert-butoxy)-1,1,1-trifluoro-6,6-dimethyl-2-(trifluoromethyl)-3-decen-2-ol | C17H28F6O2 | 详情 | 详情 | |
(VII) | 49036 | (Z)-10,10,10-trifluoro-5,5-dimethyl-9-(trifluoromethyl)-7-decene-1,9-diol | C13H20F6O2 | 详情 | 详情 | |
(VIII) | 49037 | (Z)-10,10,10-trifluoro-9-hydroxy-5,5-dimethyl-9-(trifluoromethyl)-7-decenal | C13H18F6O2 | 详情 | 详情 | |
(IX) | 49038 | (Z)-10,10,10-trifluoro-5,5-dimethyl-9-[(triethylsilyl)oxy]-9-(trifluoromethyl)-7-decenal | C19H32F6O2Si | 详情 | 详情 |