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【结 构 式】

【分子编号】49239

【品名】(1S,6R,9S,12R)-12-methoxy-6-methyl-9-(4-vinylphenyl)-10,11,13-trioxatricyclo[7.2.2.0(1,6)]tridecane; methyl (1S,6R,9S,12R)-6-methyl-9-(4-vinylphenyl)-10,11,13-trioxatricyclo[7.2.2.0(1,6)]tridec-12-yl ether

【CA登记号】

【 分 子 式 】C20H26O4

【 分 子 量 】330.42404

【元素组成】C 72.7% H 7.93% O 19.37%

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:(VIII)

The reaction of cyclohexanone (I) with acrylonitrile (II) by means of pyrrolidine gives 3-(2-oxocyclohexyl)propionitrile (III), which is condensed with methoxymethyltriphenylphosphonium chloride (IV) in THF to yield the methoxymethylene derivative (V). The condensation of propionitrile (V) with 4-bromostyrene (VI) by means of n-BuLi ethyl ether affords the styryl ketone (VII), which is cyclized by means of triphenyl phosphite and O3 (or air, methylene blue and light) to provide trioxane (VIII) as a diastereomeric mixture that is separated by column chromatography. Finally, the vinyl group of the desired diastereomer (VIII) is oxidized with KMnO4 in acetone to afford the target compound.

1 Parker, M.H.; Krasavin, M.; Posner, G.H.; Paik, I.-H.; Jeon, H.B.; Shapiro, T.A.; Antimalarial simplified 3-aryltrioxanes: Synthesis and preclinical efficacy/toxicity testing in rodents. J Med Chem 2001, 44, 19, 3054.
2 Posner, G.H.; Shapiro, T.A.; Parker, M.H.; Krasavin, M. (Johns Hopkins University); Water-soluble trioxanes as potent and safe antimalarial agents. US 6136847; WO 0059501 .
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) 11059 Cyclohexanone 108-94-1 C6H10O 详情 详情
(II) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(III) 49235 2-(beta-Cyanoethyl)cyclohexanone C9H13NO 详情 详情
(IV) 39163 (methoxymethyl)(triphenyl)phosphonium chloride 4009-98-7 C20H20ClOP 详情 详情
(V) 49236 3-[2-[(Z)-methoxymethylidene]cyclohexyl]propanenitrile C11H17NO 详情 详情
(VI) 49237 4-Bromostyrene; p-Bromostyrene 2039-82-9 C8H7Br 详情 详情
(VII) 49238 3-[2-[(Z)-methoxymethylidene]cyclohexyl]-1-(4-vinylphenyl)-1-propanone C19H24O2 详情 详情
(VIII) 49239 (1S,6R,9S,12R)-12-methoxy-6-methyl-9-(4-vinylphenyl)-10,11,13-trioxatricyclo[7.2.2.0(1,6)]tridecane; methyl (1S,6R,9S,12R)-6-methyl-9-(4-vinylphenyl)-10,11,13-trioxatricyclo[7.2.2.0(1,6)]tridec-12-yl ether C20H26O4 详情 详情
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