(4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline -Drug Synthesis Database

【结构式】

【分子编号】20465

【品名】(4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline

【CA登记号】

【分子式】C₁₇H₂₂INO

【分子量】383.27229

【元素组成】C 53.27% H 5.79% I 33.11% N 3.65% O 4.17%

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：(XIX)

Free-radical syn addition of tributyltin hydride to the triple bond of (XVII) using azobis(isobutyronitrile) as the catalyst produced the tributylstannyl compound (XVIII), which upon treatment with iodine in CHCl3 provided the trans iodopropenyl derivative (XIX). Finally, dealkylation of the methyl ether of (XIX) in boiling 48% HBr yielded the target phenol.

参考文献中间体

合成目标

【1】 Tagmatarchis, N.; Thermos, K.; Katerinopoulos, H.E.; N-(Iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and adrenergic and dopaminergic activity studies. J Med Chem 1998, 41, 21, 4165.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVII)	20463	(4aS,10aS)-1-(2-propynyl)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-6-methoxy-1-(2-propynyl)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline	C₁₇H₂₁NO	详情	详情
(XVIII)	20464	(4aS,10aS)-1-[(E)-3-(tributylstannyl)-2-propenyl]-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-6-methoxy-1-[(E)-3-(tributylstannyl)-2-propenyl]-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline	C₂₉H₄₉NOSn	详情	详情
(XIX)	20465	(4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-1-[(E)-3-iodo-2-propenyl]-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline	C₁₇H₂₂INO	详情	详情

Extended Information