4-vinylphenyl acetate -Drug Synthesis Database

【结构式】

【分子编号】27297

【品名】4-vinylphenyl acetate

【CA登记号】2628-16-2

【分子式】C₁₀H₁₀O₂

【分子量】162.1882

【元素组成】C 74.06% H 6.21% O 19.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(X)

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.

参考文献中间体

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(XV)

In a related synthesis, styrene (XV) was coupled with iodoacetophenone (VI) to afford stilbene (XVI). The benzopyranone system (XVII) was constructed by condensation with diethyl oxalate, followed by acid cyclization. Subsequent alkylation of the phenolic hydroxyl group with 4-phenylbutyl bromide (XVIII) gave the previously described ether (XIII), which was then converted into the target compound using the same reaction sequence as before.

参考文献中间体

合成目标

【1】 Cabre,M.; Borras, L.; Pascual, J.; et al.; Novel stilbene derivatives as LTD4 antagonists. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.53.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVIIII)	27300	1-(4-bromobutyl)benzene; (4-bromobutyl)benzene	13633-25-5	C₁₀H₁₃Br	详情	详情
(VI)	27290	1-(2-hydroxy-3-iodophenyl)-1-ethanone		C₈H₇IO₂	详情	详情
(XIII)	27295	ethyl 4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]ethenyl]-4H-chromene-2-carboxylate		C₃₀H₂₈O₅	详情	详情
(XIV)	27296	4-oxo-8-[(E)-2-[4-(4-phenylbutoxy)phenyl]ethenyl]-4H-chromene-2-carbonitrile		C₂₈H₂₃NO₃	详情	详情
(XV)	27297	4-vinylphenyl acetate	2628-16-2	C₁₀H₁₀O₂	详情	详情
(XVI)	27298	4-[(E)-2-(3-acetyl-2-hydroxyphenyl)ethenyl]phenyl acetate		C₁₈H₁₆O₄	详情	详情
(XVII)	27299	ethyl 8-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-oxo-4H-chromene-2-carboxylate		C₂₀H₁₆O₅	详情	详情

Extended Information