【结 构 式】 |
【分子编号】40596 【品名】(aminooxy)(hydroxy)dioxo-lambda(6)-sulfane 【CA登记号】2950-43-8 |
【 分 子 式 】H3NO4S 【 分 子 量 】113.09416 【元素组成】H 2.67% N 12.39% O 56.59% S 28.35% |
合成路线1
该中间体在本合成路线中的序号:(IV)The condensation of 7-chloro-1,2,3,4-tetrahydroquinolin-4-one (I) with 2-methylbenzoyl chloride (II) by means of pyridine in dichloromethane gives the corresponding acyl quinolone (III), which is then treated with hydroxylamine-O-sulfonic acid (IV) and K2CO3 to yield the target oxime.
【1】 Uemura, A.; Mochida, E.; Haga, A.; Tokunaga, H.; Kato, K. (Mochida Pharmaceutical Co., Ltd.); 1-Acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivs.. AU 9058618; EP 0243982; JP 1988239270; JP 1993262737; US 4739368; WO 8706580 . |
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) | 49524 | 7-chloro-2,3-dihydro-4(1H)-quinolinone | C9H8ClNO | 详情 | 详情 | |
(II) | 14770 | 2-methylbenzoyl chloride; o-Toluoyl chloride | 933-88-0 | C8H7ClO | 详情 | 详情 |
(III) | 49525 | 7-chloro-1-(2-methylbenzoyl)-2,3-dihydro-4(1H)-quinolinone | C17H14ClNO2 | 详情 | 详情 | |
(IV) | 40596 | (aminooxy)(hydroxy)dioxo-lambda(6)-sulfane | 2950-43-8 | H3NO4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:The protection of the OH group of 2-hydroxyacetonitrile (I) with TBDMS-Cl and imidazole in THF gives the silyl ether (II), which is treated with pentylmagnesium bromide (III) in ethyl ether yielding the protected 1-hydroxyoctan-3-one (IV), which is deprotected with HCl in methanol/water affording the corresponding hydroxyketone (V). Finally, this compound is treated with hydroxylamine-O-sulfonic acid in liquid ammonia.
【1】 Forman, S.A.; Miller, K.W.; Olsen, R.W.; Kloczewiak, M.A.; Addona, G.H.; Husain, S.S.; Cohen, J.B.; Pratt, M.B.; Synthesis and properties of 3-(2-hydroxyethyl)-3-N-pentyldiazirine, a photoactivable general anesthetic. J Med Chem 1999, 42, 17, 3300. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
40596 | (aminooxy)(hydroxy)dioxo-lambda(6)-sulfane | 2950-43-8 | H3NO4S | 详情 | 详情 | |
(I) | 14029 | Ethylene cyanohydrin; ECN; 3-Hydroxypropanenitrile | 109-78-4 | C3H5NO | 详情 | 详情 |
(II) | 31870 | 3-[[tert-butyl(dimethyl)silyl]oxy]propanenitrile | C9H19NOSi | 详情 | 详情 | |
(III) | 31871 | bromo(pentyl)magnesium | 693-25-4 | C5H11BrMg | 详情 | 详情 |
(IV) | 31872 | 1-[[tert-butyl(dimethyl)silyl]oxy]-3-octanone | C14H30O2Si | 详情 | 详情 | |
(V) | 31873 | 1-hydroxy-3-octanone | C8H16O2 | 详情 | 详情 |