(E)-3-(4-benzoylphenyl)-2-propenoic acid -Drug Synthesis Database

【结构式】

【分子编号】18450

【品名】(E)-3-(4-benzoylphenyl)-2-propenoic acid

【CA登记号】

【分子式】C₁₆H₁₂O₃

【分子量】252.26948

【元素组成】C 76.18% H 4.79% O 19.03%

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：(IV)

Palladium-catalyzed coupling of 4-bromobenzophenone (I) with methyl acrylate (II) afforded 4-benzoylcinnamic ester (III), which was hydrolyzed to acid (IV) with NaOH. Condensation with taxane derivative (V) in the presence of DCC and DMAP then provided the target ester.

参考文献中间体

合成目标

【1】 Bernacki, R.J.; Ojima, I. (State University of New York, Albany); Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compsns. thereof. EP 0966456; US 5811452; WO 9830553 .

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)	18447	(4-bromophenyl)(phenyl)methanone	90-90-4	C₁₃H₉BrO	详情	详情
(II)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(III)	18449	methyl (E)-3-(4-benzoylphenyl)-2-propenoate		C₁₇H₁₄O₃	详情	详情
(IV)	18450	(E)-3-(4-benzoylphenyl)-2-propenoic acid		C₁₆H₁₂O₃	详情	详情
(V)	18451	(1S,2S,4S,7R,9S,10S,12R,15R,16S)-4,12,15-tris(acetoxy)-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,17,19-trioxapentacyclo[11.6.1.0(1,16).0(3,10).0(4,7)]icos-13-en-2-yl benzoate		C₃₄H₃₈O₁₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

Heck coupling between 4-bromobenzophenone (VIII) and methyl acrylate (IX) in the presence of palladium diacetate gave the unsaturated ester (X). Subsequent basic hydrolysis of the methyl ester group of (X) yielded p-benzoylcinnamic acid (XI). The title compound was then obtained by the coupling of acid (XI) with the precursor baccatin (VII) in the presence of EDC and DMAP.

参考文献中间体

合成目标

【1】 Strum, M.; et al.; Synthesis and SAR of new taxane reversal agents. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 131.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	51205	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-tris(acetoxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate		C₃₄H₄₂O₁₃	详情	详情
(VIII)	18447	(4-bromophenyl)(phenyl)methanone	90-90-4	C₁₃H₉BrO	详情	详情
(IX)	14156	methyl acrylate	96-33-3	C₄H₆O₂	详情	详情
(X)	18449	methyl (E)-3-(4-benzoylphenyl)-2-propenoate		C₁₇H₁₄O₃	详情	详情
(XI)	18450	(E)-3-(4-benzoylphenyl)-2-propenoic acid		C₁₆H₁₂O₃	详情	详情

Extended Information