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【结 构 式】

【分子编号】50460

【品名】3,7-dimethyl-1-(10-undecenyl)-3,7-dihydro-1H-purine-2,6-dione

【CA登记号】

【 分 子 式 】C18H28N4O2

【 分 子 量 】332.44608

【元素组成】C 65.03% H 8.49% N 16.85% O 9.63%

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:(III)

The alkylation of theobromine (I) with undecenyl mesylate (II) in the presence of NaH in DMSO afforded the 1-undecenyl xanthine (III). Dihydroxylation of the terminal double bond of (III) by means of N-methylmorpholine-N-oxide and a catalytic amount of potassium osmate gave diol (IV), which was further converted to bromo acetate (V) by treatment with a solution of HBr in AcOH. Methanolysis of the bromoester (V) with concomitant cyclization gave rise to epoxide (VI). Finally, epoxide opening upon heating with dodecylamine (VII) furnished the target amino alcohol.

1 Michnick, J.; Underiner, G.E.; Klein, J.P.; Rice, G.C.; Sunkara, P.S. (Cell Therapeutics, Inc.); Second messenger cell signaling inhibitors. CH 686830; EP 0719267; JP 1996508981; US 5470878; WO 9422863 .
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) 16651 theobromine; 3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione 83-67-0 C7H8N4O2 详情 详情
(II) 50459 10-undecenyl methanesulfonate C12H24O3S 详情 详情
(III) 50460 3,7-dimethyl-1-(10-undecenyl)-3,7-dihydro-1H-purine-2,6-dione C18H28N4O2 详情 详情
(IV) 50461 1-(10,11-dihydroxyundecyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione C18H30N4O4 详情 详情
(V) 50462 1-(bromomethyl)-10-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)decyl acetate C20H31BrN4O4 详情 详情
(VI) 50463 3,7-dimethyl-1-[9-(2-oxiranyl)nonyl]-3,7-dihydro-1H-purine-2,6-dione C18H28N4O3 详情 详情
(VII) 40735 1-dodecanamine; dodecylamine 124-22-1 C12H27N 详情 详情
Extended Information