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【结 构 式】

【分子编号】44995

【品名】methyl (E)-3-(2,6-dinitrophenyl)-2-propenoate

【CA登记号】

【 分 子 式 】C10H8N2O6

【 分 子 量 】252.1834

【元素组成】C 47.63% H 3.2% N 11.11% O 38.07%

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)

The Wittig reaction of 2,6-dinitrobenzaldehyde (I) with (ethoxycarbonylmethylene)triphenylphosphorane (A) produced methyl 2,6-dinitrocinnamate (II). Hydrogenation of the nitro groups and the olefinic double bond of (II) with concomitant cyclization furnished the tetrahydroquinolinone (III). Reductive alkylation of (III) with 6,6-dimethylheptadiynal (IV) and sodium cyanoborohydride produced the secondary amine (V). Finally, the N-methyl group was introduced by a second reductive alkylation with formaldehyde.

1 Masabuchi, K.; Umeda, I.; Taniguchi, M.; et al.; Synthesis and structure-activity relationships of novel fungal chitin synthase inhibitors. Bioorg Med Chem Lett 2000, 10, 13, 1459.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 14689 Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane;Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate 2605-67-6 C21H19O2P 详情 详情
(I) 39891 2,6-dinitrobenzaldehyde 606-31-5 C7H4N2O5 详情 详情
(II) 44995 methyl (E)-3-(2,6-dinitrophenyl)-2-propenoate C10H8N2O6 详情 详情
(III) 44996 5-amino-3,4-dihydro-2(1H)-quinolinone C9H10N2O 详情 详情
(IV) 44997 6,6-dimethyl-2,4-heptadiynal C9H10O 详情 详情
(V) 44998 5-[(6,6-dimethyl-2,4-heptadiynyl)amino]-3,4-dihydro-2(1H)-quinolinone C18H20N2O 详情 详情
Extended Information