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【结 构 式】

【分子编号】31871

【品名】bromo(pentyl)magnesium

【CA登记号】693-25-4

【 分 子 式 】C5H11BrMg

【 分 子 量 】175.35134

【元素组成】C 34.25% H 6.32% Br 45.57% Mg 13.86%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(III)

The protection of the OH group of 2-hydroxyacetonitrile (I) with TBDMS-Cl and imidazole in THF gives the silyl ether (II), which is treated with pentylmagnesium bromide (III) in ethyl ether yielding the protected 1-hydroxyoctan-3-one (IV), which is deprotected with HCl in methanol/water affording the corresponding hydroxyketone (V). Finally, this compound is treated with hydroxylamine-O-sulfonic acid in liquid ammonia.

1 Forman, S.A.; Miller, K.W.; Olsen, R.W.; Kloczewiak, M.A.; Addona, G.H.; Husain, S.S.; Cohen, J.B.; Pratt, M.B.; Synthesis and properties of 3-(2-hydroxyethyl)-3-N-pentyldiazirine, a photoactivable general anesthetic. J Med Chem 1999, 42, 17, 3300.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40596 (aminooxy)(hydroxy)dioxo-lambda(6)-sulfane 2950-43-8 H3NO4S 详情 详情
(I) 14029 Ethylene cyanohydrin; ECN; 3-Hydroxypropanenitrile 109-78-4 C3H5NO 详情 详情
(II) 31870 3-[[tert-butyl(dimethyl)silyl]oxy]propanenitrile C9H19NOSi 详情 详情
(III) 31871 bromo(pentyl)magnesium 693-25-4 C5H11BrMg 详情 详情
(IV) 31872 1-[[tert-butyl(dimethyl)silyl]oxy]-3-octanone C14H30O2Si 详情 详情
(V) 31873 1-hydroxy-3-octanone C8H16O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

Dimethylaluminium chloride-catalyzed ring opening of butyrolactone (I) with N,O-dimethylhydroxylamine furnishes the N-methoxy amide (II). Subsequent condensation of the Weinreb amide (II) with pentylmagnesium bromide (III) gives rise to the hydroxy ketone (IV). Further oxidation of the primary alcohol function of (IV) under Swern conditions leads to keto aldehyde (V). Then, Wittig condensation of aldehyde (V) with (methoxycarbonylmethylene) triphenylphosphorane (VI) affords the unsaturated ester (VII). Treatment of (VII) with urea-hydrogen peroxide in the presence of scandium triflate generates the hydroperoxide compound (VIII), which undergoes further intramolecular ring closure in the presence of triethylamine, leading to the 1,2-dioxane (IX). Enzymatic hydrolysis of ester (IX) employing pig liver esterase gives acid (X). After activation of (X) as the corresponding pentafluorophenyl ester (XI), condensation with propylamine in pyridine provides the title N-propyl amide

1 Murakami, N.; Kawanishi, M.; Mostaqul, H.M.; Tsuruta, K.; Itagaki, S.; Horii, T.; Kobayashi, M.; Exploitation for new antimalarials using spongean peroxides as scaffolds. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst 1P-12.
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) 20576 dihydro-2(3H)-furanone 96-48-0 C4H6O2 详情 详情
(II) 59681 4-hydroxy-N-methoxy-N-methylbutanamide C6H13NO3 详情 详情
(III) 31871 bromo(pentyl)magnesium 693-25-4 C5H11BrMg 详情 详情
(IV) 59682 1-hydroxy-4-nonanone C9H18O2 详情 详情
(V) 59683 4-oxononanal C9H16O2 详情 详情
(VI) 14689 Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane;Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate 2605-67-6 C21H19O2P 详情 详情
(VII) 59684 methyl (E)-6-oxo-2-undecenoate C12H20O3 详情 详情
(VIII) 59685 methyl (E)-6-hydroperoxy-6-methoxy-2-undecenoate C13H24O5 详情 详情
(IX) 60083 methyl 2-(6-methoxy-6-pentyl-1,2-dioxan-3-yl)acetate C13H24O5 详情 详情
(X) 60084 2-(6-methoxy-6-pentyl-1,2-dioxan-3-yl)acetic acid C12H22O5 详情 详情
(XI) 60085 2,3,4,5,6-pentafluorophenyl 2-(6-methoxy-6-pentyl-1,2-dioxan-3-yl)acetate C18H21F5O5 详情 详情
Extended Information