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【结 构 式】

【分子编号】50096

【品名】4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl acetate

【CA登记号】

【 分 子 式 】C18H18O4

【 分 子 量 】298.33852

【元素组成】C 72.47% H 6.08% O 21.45%

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:(XI)

The reaction of 3,5-dihydroxybenzoic acid (I) with Bn-Br, K2CO3 and 18-crown-6 in refluxing acetone gives 3,5-bis(benzyloxy)benzoic acid (II), which is reduced with LiAlH4 in ethyl ether to yield the corresponding benzyl alcohol (III). The reaction of (III) with PBr3 in ethyl ether/pyridine affords the benzyl bromide (IV), which is treated with triisopropyl phosphite (V) at 140-150 C to provide the phosphonate (VI). The condensation of (VI) with 4-benzyloxybenzaldehyde (VII) by means of NaOMe in DMF gives (E)-3,4',5-tris(benzyloxy)stilbene (VIII), which is finally debenzylated by treatment with BBr3 in dichloromethane. Alternatively, the synthesis of the target product can be performed by first condensation of 3,5-dimethoxybenzoyl chloride (IX) with 4-acetoxystyrene (X) by means of palladium(II) acetate and Et3N in p-xylene to yield (E)-4-acetoxy-3',5'-dimethoxystilbene (XI), whose acetoxy group is subjected to saponification either with NaOMe or with K2CO3 in THF/H2O/MeOH and whose methoxy groups are cleaved by means of BBr3 in CH2Cl2.

1 Meredith, E.; Andrus, M. (Brigham Young University); Synthesis of resveratrol. WO 0160774 .
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) 16230 resorcylic acid; 3,5-dihydroxybenzoic acid 99-10-5 C7H6O4 详情 详情
(II) 25157 3,5-bis(benzyloxy)benzoic acid 28917-43-3 C21H18O4 详情 详情
(III) 50091 [3,5-bis(benzyloxy)phenyl]methanol C21H20O3 详情 详情
(IV) 50092 1,3-bis(benzyloxy)-5-(bromomethyl)benzene; benzyl 3-(benzyloxy)-5-(bromomethyl)phenyl ether C21H19BrO2 详情 详情
(V) 32162 Triisopropyl phosphite 116-17-6 C9H21O3P 详情 详情
(VI) 50093 diisopropyl 3,5-bis(benzyloxy)benzylphosphonate C27H33O5P 详情 详情
(VII) 29179 4-(Benzyloxy)benzaldehyde 4397-53-9 C14H12O2 详情 详情
(VIII) 50094 benzyl 3-(benzyloxy)-5-[(E)-2-[4-(benzyloxy)phenyl]ethenyl]phenyl ether; 1,3-bis(benzyloxy)-5-[(E)-2-[4-(benzyloxy)phenyl]ethenyl]benzene C35H30O3 详情 详情
(IX) 50095 3,5-Dimethoxybenzoyl chloride 17213-57-9 C9H9ClO3 详情 详情
(X) 27297 4-vinylphenyl acetate 2628-16-2 C10H10O2 详情 详情
(XI) 50096 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenyl acetate C18H18O4 详情 详情
Extended Information