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【结 构 式】

【药物名称】

【化学名称】 

【CA登记号】

【 分 子 式 】C17H22N4O2

【 分 子 量 】314.39049

【开发单位】

【药理作用】0

合成路线1

Reduction of 3,4-dimethoxybenzaldehyde (I) with NaBH4 provided benzyl alcohol (II). After conversion of (II) to the benzyl chloride (III) using SOCl2, its reaction with PPh3 (IV) in refluxing xylene afforded phosphonium salt (V). Subsequent Wittig reaction of the corresponding ylide with 4,4-(ethylenedioxy)cyclohexanone (VI) produced the benzylidene derivative (VII), which was reduced to benzyl compound (VIII) by catalytic hydrogenation over Pd/C. The ketal protecting group of (VIII) was then removed by acid hydrolysis to yield cyclohexanone (IX). Finally, the target tetrahydroquinazoline was obtained by condensation of (IX) with cyanoguanidine (X) at 180 C.

1 Papoulis, A.T.; Queener, S.F.; Rosowsky, A.; Forsch, R.A.; Synthesis and antiparasitic and antitumor activity. J Med Chem 1999, 42, 6, 1007.
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) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 23603 (3,4-dimethoxyphenyl)methanol 93-03-8 C9H12O3 详情 详情
(III) 23604 4-(chloromethyl)-2-methoxyphenyl methyl ether; 4-(chloromethyl)-1,2-dimethoxybenzene 7306-46-9 C9H11ClO2 详情 详情
(IV) 23605 trimethylphosphine 594-09-2 C3H9P 详情 详情
(V) 23606 (3,4-dimethoxybenzyl)(trimethyl)phosphonium C12H20O2P 详情 详情
(VI) 11377 1,4-Dioxaspiro[4.5]decan-8-one 4746-97-8 C8H12O3 详情 详情
(VII) 23608 8-(3,4-dimethoxybenzylidene)-1,4-dioxaspiro[4.5]decane; 4-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-2-methoxyphenyl methyl ether C17H22O4 详情 详情
(VIII) 23609 4-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)-2-methoxyphenyl methyl ether; 8-(3,4-dimethoxybenzyl)-1,4-dioxaspiro[4.5]decane C17H24O4 详情 详情
(IX) 23610 4-(3,4-dimethoxybenzyl)cyclohexanone C15H20O3 详情 详情
(X) 23611 N-cyanoguanidine 461-58-5 C2H4N4 详情 详情
Extended Information