1-(4-bromobutyl)benzene; (4-bromobutyl)benzene -Drug Synthesis Database

【结构式】

【分子编号】27300

【品名】1-(4-bromobutyl)benzene; (4-bromobutyl)benzene

【CA登记号】13633-25-5

【分子式】C₁₀H₁₃Br

【分子量】213.11722

【元素组成】C 56.36% H 6.15% Br 37.49%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XVIIII)

In a related synthesis, styrene (XV) was coupled with iodoacetophenone (VI) to afford stilbene (XVI). The benzopyranone system (XVII) was constructed by condensation with diethyl oxalate, followed by acid cyclization. Subsequent alkylation of the phenolic hydroxyl group with 4-phenylbutyl bromide (XVIII) gave the previously described ether (XIII), which was then converted into the target compound using the same reaction sequence as before.

参考文献中间体

合成目标

【1】 Cabre,M.; Borras, L.; Pascual, J.; et al.; Novel stilbene derivatives as LTD4 antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.53.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVIIII)	27300	1-(4-bromobutyl)benzene; (4-bromobutyl)benzene	13633-25-5	C₁₀H₁₃Br	详情	详情
(VI)	27290	1-(2-hydroxy-3-iodophenyl)-1-ethanone		C₈H₇IO₂	详情	详情
(XIII)	27295	ethyl 4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]ethenyl]-4H-chromene-2-carboxylate		C₃₀H₂₈O₅	详情	详情
(XIV)	27296	4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]ethenyl]-4H-chromene-2-carbonitrile		C₂₈H₂₃NO₃	详情	详情
(XV)	27297	4-vinylphenyl acetate	2628-16-2	C₁₀H₁₀O₂	详情	详情
(XVI)	27298	4-[(E)-2-(3-acetyl-2-hydroxyphenyl)ethenyl]phenyl acetate		C₁₈H₁₆O₄	详情	详情
(XVII)	27299	ethyl 8-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-oxo-4H-chromene-2-carboxylate		C₂₀H₁₆O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Treatment of 4-phenylbutanol (I) with PBr3 gave the corresponding bromide (II). 6-Methoxytryptamine (III) was converted to the hydrochloride salt, and then condensed with formaldehyde under Pictet-Spengler conditions to furnish the pyridoindole system (IV). Alkylation of amine (IV) with bromide (II) then gave the phenylbutyl amine (V). Finally, O-demethylation of (V) employing BBr3 yielded the title compound.

参考文献中间体

合成目标

【1】 Becker, R.E.; Thornton, S.L.; Moriearty, P.L.; Transdermal patch delivery of acetylcholinesterase inhibitors. Methods Find Exp Clin Pharmacol 1993, 15, 6, 407.

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)	27291	4-phenyl-1-butanol	3360-41-6	C₁₀H₁₄O	详情	详情
(II)	27300	1-(4-bromobutyl)benzene; (4-bromobutyl)benzene	13633-25-5	C₁₀H₁₃Br	详情	详情
(III)	35822	6-Methoxytryptamine; 3-(2-Aminoethyl)-6-methoxyindole; 2-(6-Methoxy-1H-indol-3-yl)-1-ethanamine; 2-(6-Methoxy-1H-indol-3-yl)ethylamine	3610-36-4	C₁₁H₁₄N₂O	详情	详情
(IV)	35823	7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline; methyl 2,3,4,9-tetrahydro-1H-beta-carbolin-7-yl ether		C₁₂H₁₄N₂O	详情	详情
(V)	35824	7-methoxy-2-(4-phenylbutyl)-2,3,4,9-tetrahydro-1H-beta-carboline; methyl 2-(4-phenylbutyl)-2,3,4,9-tetrahydro-1H-beta-carbolin-7-yl ether		C₂₂H₂₆N₂O	详情	详情

Extended Information