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【结 构 式】

【分子编号】18558

【品名】1,2,4,4a,5,6-hexahydro-3H-pyrido[1,2-a]quinolin-3-one

【CA登记号】

【 分 子 式 】C13H15NO

【 分 子 量 】201.26824

【元素组成】C 77.58% H 7.51% N 6.96% O 7.95%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Dihydroquinolinone (I) was protected as the tert-butyl carbamate (II) by condensation with di-tert-butyl dicarbonate. Reduction of (II) with NaBH4 in EtOH at -25 C, followed by reaction with ethanolic HCl provided ethoxy compound (III). Subsequent treatment of (III) with 2-silyloxy-1,3-butadiene (V) and trimethylsilyl triflate afforded benzoquinolizinone (VI), through the sequence of Mannich condensation of intermediate N-tert-Boc iminium salt (IV) with silyl enol ether (V), followed by Michael cyclization of the unsaturated ketone. Then, oxidation with mercuric acetate provided the target 4-4a unsaturated compound together with a minor amount of 1,2-unsaturated product.

1 Guarna, A.; Occhiato, E.G.; Scarpi, D.; Tsai, R.; Danza, G.; Comerci, A.; Mancina, R.; Serio, M.; Synthesis of benzo[c]quinolizin-3-ones: Selective non-steroidal inhibitors of steroid 5alpha-reductase 1. Bioorg Med Chem Lett 1998, 8, 20, 2871.
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) 18553 3,4-dihydro-2(1H)-quinolinone 553-03-7 C9H9NO 详情 详情
(II) 18554 tert-butyl 2-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate C14H17NO3 详情 详情
(III) 18555 tert-butyl 2-ethoxy-3,4-dihydro-1(2H)-quinolinecarboxylate C16H23NO3 详情 详情
(IV) 18556 tert-butyl 3,4-dihydro-1lambda(5)-quinoline-1-carboxylate C14H19NO2 详情 详情
(V) 18557 1-methylene-2-propenyl trimethylsilyl ether; trimethyl[(1-methylene-2-propenyl)oxy]silane 38053-91-7 C7H14OSi 详情 详情
(VI) 18558 1,2,4,4a,5,6-hexahydro-3H-pyrido[1,2-a]quinolin-3-one C13H15NO 详情 详情
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