(3,4-dimethoxyphenyl)methanol -Drug Synthesis Database

【结构式】

【分子编号】23603

【品名】(3,4-dimethoxyphenyl)methanol

【CA登记号】93-03-8

【分子式】C₉H₁₂O₃

【分子量】168.19248

【元素组成】C 64.27% H 7.19% O 28.54%

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：(II)

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.

参考文献中间体

合成目标

【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