1,10-dibromodecane -Drug Synthesis Database

【结构式】

【分子编号】18615

【品名】1,10-dibromodecane

【CA登记号】4101-68-2

【分子式】C₁₀H₂₀Br₂

【分子量】300.0768

【元素组成】C 40.03% H 6.72% Br 53.26%

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：(II)

Alkylation of potassium phthalimide (I) with an excess of 1,10-dibromodecane (II) in refluxing acetone afforded N-(10-bromodecyl)phthalimide (III). This was condensed with 6-O-demethylgalanthamine (IV) in the presence of Et3N in boiling acetonitrile to give phthalimidodecyl compound (V). Finally, reaction with N-bromosuccinimide in the presence of azobisisobutyronitrile provided the iminium bromide.

参考文献中间体

合成目标

【1】 Mary, A.; Renko, D.Z.; Guillou, C.; Thal, C.; Potent acetylcholinesterase inhibitors: Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998, 6, 10, 1835.

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)	10929	3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one		C₁₀H₁₈N₂O	详情	详情
(II)	18615	1,10-dibromodecane	4101-68-2	C₁₀H₂₀Br₂	详情	详情
(III)	18616	2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione	24566-80-1	C₁₈H₂₄BrNO₂	详情	详情
(IV)	18612	(6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol		C₁₆H₁₉NO₃	详情	详情
(V)	18618	2-[10-[(6R,8aS)-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]decyl]-1H-isoindole-1,3(2H)-dione		C₃₄H₄₂N₂O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Grignard reagent (II), prepared from 4-chlorobromobenzene (I) and Mg in refluxing THF, was coupled with 1,10-dibromodecane (III) in the presence of Li2CuCl4 as the catalyst to afford the bromodecyl compound (IV). Then, the dianion of dichloroacetic acid (V), generated in the presence of two equivalents of LDA in cold THF, was alkylated with bromide (IV) to provide the title compound.

参考文献中间体

合成目标

【1】 Meyer, K.; et al.; omega-Substituted alkyl carboxylic acids as antidiabetic and lipid-lowering agents. Eur J Med Chem 1998, 33, 10, 775.

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)	14733	4-Bromochlorobenzene; 1-bromo-4-chlorobenzene	106-39-8	C₆H₄BrCl	详情	详情
(II)	25127	bromo(4-chlorophenyl)magnesium	873-77-8	C₆H₄BrClMg	详情	详情
(III)	18615	1,10-dibromodecane	4101-68-2	C₁₀H₂₀Br₂	详情	详情
(IV)	25128	1-(10-bromodecyl)-4-chlorobenzene		C₁₆H₂₄BrCl	详情	详情
(V)	25129	2,2-dichloroacetic acid	79-43-6	C₂H₂Cl₂O₂	详情	详情

Extended Information