1-bromo-2-heptadecanone -Drug Synthesis Database

【结构式】

【分子编号】42357

【品名】1-bromo-2-heptadecanone

【CA登记号】

【分子式】C₁₇H₃₃BrO

【分子量】333.35242

【元素组成】C 61.25% H 9.98% Br 23.97% O 4.8%

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：(VI)

The condensation of palmitoyl chloride (IV) with diazomethane produced diazoketone (V). This was then treated with HBr to yield bromoketone (VI).

参考文献中间体

合成目标

【1】 Gandour, R.D.; et al.; (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransfease-I in intact mitochondria. J Med Chem 1993, 36, 2, 237.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	30295	tetradecanoyl chloride	112-64-1	C₁₄H₂₇ClO	详情	详情
(V)	42356			C₁₅H₂₈N₂O	详情	详情
(VI)	42357	1-bromo-2-heptadecanone		C₁₇H₃₃BrO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

In a different procedure, treatment of olefin (VII) with N-bromosuccinimide produced bromohydrin (VIII), which was further oxidized to bromoketone (VI) by means of Jones reagent. Condensation of bromoketone (VI) with aminoalcohol (III) in nitromethane furnished the morpholine derivative (IX). The ester group was finally hydrolyzed with to yield the title compound.

参考文献中间体

合成目标

【1】 Bryant, S.D.; Hubieki, M.P.; Robinette, R.G.; Gandourk, R.D.; Savle, P.S.; Doncel, G.F.; Acylcarnitine analogues as topical, microbicidal spermicides. Bioorg Med Chem Lett 1999, 9, 17, 2545.
【2】 Gandour, R.D.; et al.; (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransfease-I in intact mitochondria. J Med Chem 1993, 36, 2, 237.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	42355	methyl (3R)-4-(dimethylamino)-3-hydroxybutanoate		C₇H₁₅NO₃	详情	详情
(VI)	42357	1-bromo-2-heptadecanone		C₁₇H₃₃BrO	详情	详情
(VII)	42358	1-heptadecene	6765-39-5	C₁₇H₃₄	详情	详情
(VIII)	42359	1-bromo-2-heptadecanol		C₁₇H₃₅BrO	详情	详情
(IX)	42360	(2S,6R)-2-hydroxy-6-(2-methoxy-2-oxoethyl)-4,4-dimethyl-2-pentadecylmorpholin-4-ium bromide		C₂₄H₄₈BrNO₄	详情	详情

Extended Information