1-(4-bromophenyl)-1,3-butanedione -Drug Synthesis Database

【结构式】

【分子编号】61315

【品名】1-(4-bromophenyl)-1,3-butanedione

【CA登记号】

【分子式】C₁₀H₉BrO₂

【分子量】241.08426

【元素组成】C 49.82% H 3.76% Br 33.14% O 13.27%

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：(II)

Claisen condensation of 4-bromoacetophenone (I) with ethyl acetate provides diketone (II). Subsequent reaction of (II) with carbon disulfide in the presence of LDA leads to thiopyranone thiol (III). Alkylation of thiol (III) with iodoethane and K2CO3 affords sulfide (IV), which is further oxidized to sulfoxide (V) by means of mCPBA. Displacement of either sulfide (IV) or sulfoxide (V) with morpholine gives rise to the morpholinyl thiopyranone (VI). Finally, Suzuki coupling between aryl bromide (VI) and 2-naphthaleneboronic acid (VII) produces the target compound

参考文献中间体

合成目标

【1】 Griffin, R.J.; Combinatorial methods for identifying antitumour kinase inhibitors. Eur J Cancer 2002, 38, Suppl. 7.

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)	25421	1-(4-bromophenyl)-1-ethanone	99-90-1	C₈H₇BrO	详情	详情
(II)	61315	1-(4-bromophenyl)-1,3-butanedione		C₁₀H₉BrO₂	详情	详情
(III)	61316	2-(4-bromophenyl)-6-sulfanyl-4H-thiopyran-4-one		C₁₁H₇BrOS₂	详情	详情
(IV)	61317	2-(4-bromophenyl)-6-(ethylsulfanyl)-4H-thiopyran-4-one		C₁₃H₁₁BrOS₂	详情	详情
(V)	61318	2-(4-bromophenyl)-6-(ethylsulfinyl)-4H-thiopyran-4-one		C₁₃H₁₁BrO₂S₂	详情	详情
(VI)	61319	2-(4-bromophenyl)-6-(4-morpholinyl)-4H-thiopyran-4-one		C₁₅H₁₄BrNO₂S	详情	详情
(VII)	27703	1-naphthylboronic acid	13922-41-3	C₁₀H₉BO₂	详情	详情

Extended Information