【结 构 式】 |
【分子编号】30488 【品名】4-(4-isopropyl-1-piperazinyl)phenol; 1-Isopropyl-4-(4-hydroxyphenyl)piperazine 【CA登记号】 |
【 分 子 式 】C13H20N2O 【 分 子 量 】220.31468 【元素组成】C 70.87% H 9.15% N 12.72% O 7.26% |
合成路线1
该中间体在本合成路线中的序号:(A)The condensation of 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-(benzoyloxymethyl)-1,3-dioxolane (I) with triazole (II) by means of NaH in DMSO, followed by hydrolysis with NaOH in dioxane water gives 2-(2,4-dichlorophenyl)-2-(1H)-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol (III), which is acylated with methanesulfonyl chloride in pyridine affording the corresponding 4-mesyloxymethyldioxolane (IV). Finally, this compound is condensed with 4-(4-isopropylpiperazin-1-yl)phenol (V) by means of NaH in hot DMSO. Compound (V) is obtained as follows: 4-(4-methoxyphenyl)piperazine (VI) is reductocondensed with acetone (A) by means of H2 over Pd/C giving 1-isopropyl-4-(4-methoxyphenyl)piperazine (VII), which is then demethylated with refluxing aqueous 48% HBr yielding (V)
【1】 Van Cutsem, J.; Heeres, J.; Hendrickx, R.; Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal. J Med Chem 1983, 26, 4, 611-613. |
【2】 Heeres, J.; Backx, L.J.J.; Mostmans, J.H. (Janssen Pharmaceutica NV); Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles. BE 0863382; FR 2378778; GB 1594859; JP 7895973; US 4144346; US 4223036 . |
【3】 Serradell, M.N.; Castaner, J.; Fromtling, R.A.; Terconazole. Drugs Fut 1984, 9, 7, 529. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(A) | 30488 | 4-(4-isopropyl-1-piperazinyl)phenol; 1-Isopropyl-4-(4-hydroxyphenyl)piperazine | C13H20N2O | 详情 | 详情 | |
(I) | 30485 | [(2S,4S)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate; cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate | C18H15BrCl2O4 | 详情 | 详情 | |
(II) | 13135 | 1H-1,2,4-Triazole; 1,2,4-Triazole | 288-88-0 | C2H3N3 | 详情 | 详情 |
(III) | 30486 | [(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methanol | C13H13Cl2N3O3 | 详情 | 详情 | |
(IV) | 30487 | 1-[[(2S,4S)-2-(2,4-dichlorophenyl)-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole | C16H19Cl2N3O3S | 详情 | 详情 | |
(V) | 16312 | 1-(4-Methoxyphenyl)piperazine; Methyl 4-piperazinophenyl ether | 38212-30-5 | C11H16N2O | 详情 | 详情 |
(VI) | 23199 | 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one; Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether | 67-64-1 | C3H6O | 详情 | 详情 |
(VII) | 30489 | 1-isopropyl-4-(4-methoxyphenyl)piperazine; 4-(4-isopropyl-1-piperazinyl)phenyl methyl ether | C14H22N2O | 详情 | 详情 |