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【结 构 式】

【分子编号】62351

【品名】1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine

【CA登记号】

【 分 子 式 】C9H17NO2

【 分 子 量 】171.23952

【元素组成】C 63.13% H 10.01% N 8.18% O 18.69%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The condensation of 2-(chloromethyl)-1,4-dioxaspiro[4,5]decane (I) with the sodium salt of phthalimide (II) in hot DMF affords the N-substituted phthalimide (III). Subsequent phthaloyl group hydrazinolysis gives the primary amine (IV). Finally, condensation of amine (IV) with S-methyl pseudothiourea sulfate (V) leads to the title guanidine derivative

1 Aaron, J.E. Jr.; Hardie, W.R.; Process for the preparation of 1,3-dioxolan-4-yl-alcoyl-guanidines and its intermediates. FR 1522153 .
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) 62349 2-(chloromethyl)-1,4-dioxaspiro[4.5]decane C9H15ClO2 详情 详情
(II) 12376 Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione 85-41-6 C8H5NO2 详情 详情
(III) 62350 2-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)-1H-isoindole-1,3(2H)-dione C17H19NO4 详情 详情
(IV) 62351 1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine C9H17NO2 详情 详情
(V) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

In a different method, acetylation of 3-amino-1,2-propanediol (I) yields the amide diol (II). Ketalization of cyclohexanone (III) with diol (II) furnishes the spiro dioxolane (IV). The acetamide function of (IV) is then hydrolyzed to amine (V) employing aqueous hydrazine. Amine (V) is condensed with N,N'-di-(carbobenzoxy)-N''-(trifluoromethylsulfonyl)guanidine (VI) to produce the protected guanidine (VII). The N-carbobenzoxy groups of (VII) are finally removed by hydrogenolysis over Pd/C. Alternatively, amine (V) is condensed with cyanogen bromide to produce the cyanamide (VIII). Then, reaction of cyanamide (VIII) with ammonium chloride in aqueous ammonia furnishes the title guanidine compound

1 Xian, M.; Li, X.; Tang, X.; Chen, X.; Zheng, Z.; Galligan, J.J.; Kreulen, D.L.; Wang, P.G.; N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors. Bioorg Med Chem Lett 2001, 11, 17, 2377.
2 Xiao, J.-H.; et al.; Endogenous retinoic acid receptor (RAR)-retinoid X receptor (RXR) heterodimers are the major functional forms regulating retinoid-responsive elements in adult human keratinocytes. Binding of ligands to RAR only is sufficient for RAR.RXR heterodimers to co. J Biol Chem 1995, 270, 7, 3001.
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) 12979 3-Amino-1,2-propanediol;3-aminopropane-1,2-diol 616-30-8 C3H9NO2 详情 详情
(II) 62352 N-(2,3-dihydroxypropyl)acetamide C5H11NO3 详情 详情
(III) 11059 Cyclohexanone 108-94-1 C6H10O 详情 详情
(IV) 62353 N-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)acetamide C11H19NO3 详情 详情
(V) 62351 1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine C9H17NO2 详情 详情
(VI) 62354   C18H19N3O4 详情 详情
(VII) 62356 benzyl (Z)-{[(benzyloxy)carbonyl]amino}[(1,4-dioxaspiro[4.5]dec-2-ylmethyl)amino]methylidenecarbamate C26H31N3O6 详情 详情
(VIII) 62355 1,4-dioxaspiro[4.5]dec-2-ylmethylcyanamide C10H16N2O2 详情 详情
Extended Information