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【结 构 式】 
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【分子编号】23608 【品名】8-(3,4-dimethoxybenzylidene)-1,4-dioxaspiro[4.5]decane; 4-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-2-methoxyphenyl methyl ether 【CA登记号】 |
【 分 子 式 】C17H22O4 【 分 子 量 】290.35928 【元素组成】C 70.32% H 7.64% O 22.04% |
合成路线1
该中间体在本合成路线中的序号：(VII)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 |