1-iodo-4-phenyl-2-butanone -Drug Synthesis Database

【结构式】

【分子编号】59557

【品名】1-iodo-4-phenyl-2-butanone

【CA登记号】

【分子式】C₁₀H₁₁IO

【分子量】274.10121

【元素组成】C 43.82% H 4.04% I 46.3% O 5.84%

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：(III)

The required phosphonate reagent (IV) was prepared by two alternative methods. Bromination of benzylacetone (I) in cold methanol afforded 1-bromo-4-phenyl-2-butanone (II). Subsequent displacement of the bromide ion of (II) with NaI in acetone led to the iodo ketone (III). The desired phosphonate (IV) was then obtained by the Arbuzov reaction of (III) with trimethyl phosphite. Alternatively, alkylation of the dianion of dimethyl 2-oxopropyl phosphonate (V) with benzyl bromide led to phosphonate (IV).

参考文献中间体

合成目标

【1】 Gutman, A.; Nisnevich, G.; Etinger, M.; Zaltzman, I.; Judovich, L.; Pertsikov, B.; A new process for the preparation of latanoprost. WO 0155101 .
【2】 Resul, B.; et al.; Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J Med Chem 1993, 36, 2, 243.

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)	32061	4-phenyl-2-butanone	2550-26-7	C₁₀H₁₂O	详情	详情
(II)	29211	1-bromo-4-phenyl-2-butanone		C₁₀H₁₁BrO	详情	详情
(III)	59557	1-iodo-4-phenyl-2-butanone		C₁₀H₁₁IO	详情	详情
(IV)	59558	dimethyl 2-oxo-4-phenylbutylphosphonate		C₁₂H₁₇O₄P	详情	详情
(V)	59559	Dimethyl acetonylphosphonate; Acetylmethylphosphonic acid dimethyl ester; Dimethyl (2-oxopropyl)phosphonate	4202-14-6	C₅H₁₁O₄P	详情	详情

Extended Information