6-methyl-2-(methylsulfanyl)-1-(3-oxopentyl)-3,4-dihydroquinolinium -Drug Synthesis Database

【结构式】

【分子编号】50346

【品名】6-methyl-2-(methylsulfanyl)-1-(3-oxopentyl)-3,4-dihydroquinolinium

【CA登记号】

【分子式】C₁₆H₂₂NOS

【分子量】276.42282

【元素组成】C 69.52% H 8.02% N 5.07% O 5.79% S 11.6%

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：(V)

The reaction of 6-methyl-1,2,3,4-tetrahydroquinolin-2-one (I) with Lawesson's reagent in refluxing toluene gives 6-methyl-1,2,3,4-tetrahydroquinolin-2-thione (II), which is condensed with ethyl vinyl ketone (III) by means of K2CO3 or DBU in THF to yield the addition product (IV). The reaction of (IV) with dimethyl sulfate in refluxing toluene affords the thioiminium ion (V), which, without isolation, is cyclized to the target compound by reaction with DBU in refluxing toluene.

参考文献中间体

合成目标

【1】 Guarna, A.; et al.; Modification of the aza-robinson annulation for the synthesis of 4-methyl-benzol[c]quinoliin-3-ones. Potent inhibitors of steroid 5alpha-reductase 1. J Org Chem 2000, 65, 23, 8093.

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)	43926	6-methyl-3,4-dihydro-2(1H)-quinolinone		C₁₀H₁₁NO	详情	详情
(II)	50344	6-methyl-3,4-dihydro-2(1H)-quinolinethione		C₁₀H₁₁NS	详情	详情
(III)	43930	1-penten-3-one	1629-58-9	C₅H₈O	详情	详情
(IV)	50345	1-[6-methyl-2-thioxo-3,4-dihydro-1(2H)-quinolinyl]-3-pentanone		C₁₅H₁₉NOS	详情	详情
(V)	50346	6-methyl-2-(methylsulfanyl)-1-(3-oxopentyl)-3,4-dihydroquinolinium		C₁₆H₂₂NOS	详情	详情

Extended Information