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【结 构 式】

【分子编号】20451

【品名】3'-Allyl-5'-methoxy-1',2',3',4'-tetrahydrospiro[1,3-dioxolan-2,2'-naphthalene]

【CA登记号】

【 分 子 式 】C16H20O3

【 分 子 量 】260.333

【元素组成】C 73.82% H 7.74% O 18.44%

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:(V)

Ketoester (II) was prepared by condensation of dimethyl carbonate with 5-methoxy-2-tetralone (I) in the presence of NaOMe. The alkylation of (II) with allyl bromide using two equivalents of LDA at -78 C proceeded selectively on the C-3 position to give (III). Further decarbomethoxylation of (III) was carried out with LiCl in moist DMSO at high temperature, and the resulting ketone (IV) was converted to ethylene ketal (V) with ethylene glycol and p-TsOH. Then, hydroboration of (V) with disiamyl borane (VI) in cold THF, followed by oxidation of borane (VII) with H2O2-NaOH furnished the primary alcohol (VIII). After Jones oxidation of alcohol (VIII), the resulting acid (IX) was esterified with MeOH and H2SO4 to give ketoester (X). Subsequent cyclization of (X) with benzylamine (XI) and AcOH in refluxing benzene afforded the intermediate tricyclic enamide (XII), which was sequentially reduced with LiAlH4 to enamine (XIII), and then with NaBH4 in the presence of AcOH to furnish a mixture of cis and trans octahydrobenzo[g]quinolines (XIV). Separation of the major trans isomer by flash chromatography was followed by hydrogenolysis of the benzyl group over Pd/C, yielding the secondary amine (XV), whitch was N-alkylated with propargyl bromide (XVI) in hot DMF to give (XVII).

1 Tagmatarchis, N.; Thermos, K.; Katerinopoulos, H.E.; N-(Iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and adrenergic and dopaminergic activity studies. J Med Chem 1998, 41, 21, 4165.
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) 14647 5-methoxy-3,4-dihydro-2(1H)-naphthalenone 32940-15-1 C11H12O2 详情 详情
(II) 20448 methyl 5-methoxy-2-oxo-1,2,3,4-tetrahydro-1-naphthalenecarboxylate C13H14O4 详情 详情
(III) 20449 methyl 3-allyl-5-methoxy-2-oxo-1,2,3,4-tetrahydro-1-naphthalenecarboxylate C16H18O4 详情 详情
(IV) 20450 3-allyl-5-methoxy-3,4-dihydro-2(1H)-naphthalenone C14H16O2 详情 详情
(V) 20451 3'-Allyl-5'-methoxy-1',2',3',4'-tetrahydrospiro[1,3-dioxolan-2,2'-naphthalene] C16H20O3 详情 详情
(VI) 20452 bis(1,2-dimethylpropyl)borane 132509-17-2 C10H23B 详情 详情
(VII) 20453 B-[3-[5'-Methoxy-1',2',3',4'-tetrahydrospiro[1,3-dioxolan-2,2'-naphthalen]-3'-yl]propyl]-B,B-bis(1,2-dimethylpropyl)borane C26H43BO3 详情 详情
(VIII) 20454 3-[5'-Methoxy-1',2',3',4'-tetrahydrospiro[1,3-dioxolan-2,2'-naphthalen]-3'-yl]propan-1-ol C16H22O4 详情 详情
(IX) 20455 3-(8-methoxy-3-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)propionic acid C14H16O4 详情 详情
(X) 20456 methyl 3-(8-methoxy-3-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)propanoate C15H18O4 详情 详情
(XI) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(XII) 20458 1-benzyl-6-methoxy-3,4,4a,5-tetrahydrobenzo[g]quinolin-2(1H)-one C21H21NO2 详情 详情
(XIII) 20459 1-benzyl-6-methoxy-1,2,3,4,4a,5-hexahydrobenzo[g]quinoline; 1-benzyl-1,2,3,4,4a,5-hexahydrobenzo[g]quinolin-6-yl methyl ether C21H23NO 详情 详情
(XIV) 20460 1-benzyl-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline; 1-benzyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether C21H25NO 详情 详情
(XV) 20461 (4aS,10aS)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline C14H19NO 详情 详情
(XVI) 11176 3-Bromopropyne; 3-Bromo-1-propyne 106-96-7 C3H3Br 详情 详情
(XVII) 20463 (4aS,10aS)-1-(2-propynyl)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl methyl ether; (4aS,10aS)-6-methoxy-1-(2-propynyl)-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline C17H21NO 详情 详情
Extended Information