methyl 3-(4'-hydroxy-3'-tricyclo[3.3.1.1~3,7~]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】63331

【品名】methyl 3-(4'-hydroxy-3'-tricyclo[3.3.1.1~3,7~]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoate

【CA登记号】

【分子式】C₂₆H₂₈O₃

【分子量】388.50652

【元素组成】C 80.38% H 7.26% O 12.35%

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)

Friedel-Crafts condensation of 4'-bromobiphenyl-4-ol (I) with 1-adamantanol (II) affords the adamantanylbiphenyl derivative (III). This is then subjected to Heck coupling with methyl acrylate (IV) to produce the biphenylyl acrylate (V). Finally, basic hydrolysis of ester (V) leads to the title carboxylic acid.

参考文献中间体

合成目标

【1】 Cincinelli, R.; Dallavalle, S.; Merlini, L.; Penco, S.; Pisano, C.; Carminati, P.; Giannini, G.; Vesci, L.; Gaetano, C.; Illy, B.; Zuco, V.; Supino, R.; Zunino, F.; A novel atypical retinoid endowed with proapoptotic and antitumor activity. J Med Chem 2003, 46, 6, 909.
【2】 Penco, S.; Merlini, L.; Giannini, G.; Vesci, L.; Pisano, C.; Dallavalle, S. (Sigma-Tau Industrie Farmaceutiche Riunite SpA); Retinoid derivs. with antiangiogenic, antitumoral and proapoptotic activities. WO 0311808 .

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)	48853	4-(4-Bromophenyl)phenol; 4-(4'-Bromophenyl)phenol; 4-Bromo-4'-hydroxybiphenyl	29558-77-8	C₁₂H₉BrO	详情	详情
(II)	52642	1-Adamantanol; 1-Hydroxyadamantane; Tricyclo[3.3.1.1]decan-1-ol	768-95-6	C₁₀H₁₆O	详情	详情
(III)	63330	4'-bromo-3-tricyclo[3.3.1.1~3,7~]dec-1-yl[1,1'-biphenyl]-4-ol		C₂₂H₂₃BrO	详情	详情
(IV)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(V)	63331	methyl 3-(4'-hydroxy-3'-tricyclo[3.3.1.1~3,7~]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoate		C₂₆H₂₈O₃	详情	详情

Extended Information