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【结 构 式】

【分子编号】18458

【品名】3-hydroxy-1,4-diphenyl-2-butanone

【CA登记号】

【 分 子 式 】C16H16O2

【 分 子 量 】240.30184

【元素组成】C 79.97% H 6.71% O 13.32%

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)

Addition of benzylmagnesium chloride to O-(trimethylsilyl)cyanohydrin (II) (obtained from phenylacetaldehyde (I) and Me3SiCN), led to benzylacyloin (III). Esterification with ethyl oxalyl chloride (IV) in the presence of Et3N afforded oxalate (V), which was cyclized with DBU in cold DMF to provide dihydrogrevillin (VI). This was methylated with ethereal diazomethane to give ether (VII), and then brominated in AcOH. Elimination of the resulting bromide (VIII) by treatment with DBU produced (IX), which was demethylated with BBr3 to afford grevillin (X). This compound was isomerized with NaOEt in EtOH to produce terphenyl quinone (XI). Finally, Perkin reaction with phenylacetic acid (XII), followed by treatment with HBr furnished the title compound.

1 Pattenden, G.; et al.; Synthesis of grevillins and their biogenetic interrelationship with terphenylquinones, xylerythrins and pulvinic acids. Tetrahedron Lett 1987, 28, 4, 4749.
2 Pattenden, G.; et al.; Synthesis of grevillins, novel pyrandione pigments of fungi. Biogenetic ibnterrelationships between grevillins, pulvinic acids, terphenylquinones and xylerythrins. J Chem Soc - Perkins Trans I 1991, 2363.
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) 18456 2-phenylacetaldehyde 122-78-1 C8H8O 详情 详情
(II) 18457 3-phenyl-2-[(trimethylsilyl)oxy]propanenitrile C12H17NOSi 详情 详情
(III) 18458 3-hydroxy-1,4-diphenyl-2-butanone C16H16O2 详情 详情
(IV) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(V) 18460 1-benzyl-2-oxo-3-phenylpropyl 2-ethoxy-2-oxoacetate C20H20O5 详情 详情
(VI) 18461 6-benzyl-3-hydroxy-4-phenyl-2H-pyran-2,5(6H)-dione C18H14O4 详情 详情
(VII) 18462 6-benzyl-3-methoxy-4-phenyl-2H-pyran-2,5(6H)-dione C19H16O4 详情 详情
(VIII) 18463 6-benzyl-6-bromo-3-methoxy-4-phenyl-2H-pyran-2,5(6H)-dione C19H15BrO4 详情 详情
(IX) 18464 3-methoxy-4-phenyl-6-[(Z)-benzylidene]-2H-pyran-2,5-dione C19H14O4 详情 详情
(X) 18465 3-hydroxy-4-phenyl-6-[(Z)-benzylidene]-2H-pyran-2,5-dione C18H12O4 详情 详情
(XI) 18466 2,5-dihydroxy-3,6-diphenylbenzo-1,4-quinone 548-59-4 C18H12O4 详情 详情
(XII) 16143 3-(4-iodobutyl)-1-[[(E)-benzylidene]amino]-1H-imidazole-2,4(3H,5H)-dione C14H16IN3O2 详情 详情
Extended Information