4-chloro-1,1'-biphenyl -Drug Synthesis Database

【结构式】

【分子编号】20252

【品名】4-chloro-1,1'-biphenyl

【CA登记号】2051-62-9

【分子式】C₁₂H₉Cl

【分子量】188.65616

【元素组成】C 76.4% H 4.81% Cl 18.79%

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：(I)

The Friedel-Crafts condensation of 4-chlorobiphenyl (I) with 3-methylenetetrahydrofuran-2,5-dione (II) by means of AlCl3 in tetrachloroethane gives 4-(4'-chlorobiphenyl-4-yl)-2-methylene-4-oxobutyric acid (III), which is treated with thiophenol (IV) and K2CO3 in DMF/water, yielding racemic 4-(4'-chlorobiphenyl-4-yl)-4-oxo-2-(phenylsulfanylmethyl)butyric acid (V). Finally, racemic (V) is resolved by means of crystallization with (+)-cinchonine in acetone.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Graul, A.; Silvestre, J.S.; Bay-12-9566. Drugs Fut 1999, 24, 1, 16.
【2】 Kluender, H.C.E.; Benz, G.H.H.H.; Brittelli, D.R.; Bullock, W.H.; Combs, K.J.; Dixon, B.R.; Schneider, S.; Wood, J.E.; Vanzandt, M.C.; Wolanin, D.J.; Wilhelm, S.M. (Bayer AG); Substd. 4-biarylbutyric or 5-biarylpentanoic acids and derivs. as matrix metalloprotease inhibitors. EP 0790974; JP 1998509146; US 5789434; US 5859047; WO 9615096 .

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)	20252	4-chloro-1,1'-biphenyl	2051-62-9	C₁₂H₉Cl	详情	详情
(II)	12891	3-Methylenedihydro-2,5-furandione; Itaconic anhydride	2170-03-8	C₅H₄O₃	详情	详情
(III)	20254	2-[2-(4'-chloro[1,1'-biphenyl]-4-yl)-2-oxoethyl]acrylic acid		C₁₇H₁₃ClO₃	详情	详情
(IV)	12951	Benzenethiol; Phenylmercaptan; Phenylhydrosulfide	108-98-5	C₆H₆S	详情	详情
(V)	20256	4-(4'-chloro[1,1'-biphenyl]-4-yl)-4-oxo-2-[(phenylsulfanyl)methyl]butyric acid		C₂₃H₁₉ClO₃S	详情	详情

Extended Information