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【结 构 式】

【分子编号】29479

【品名】3-hydroxy-2-cyclohexen-1-one N-phenylhydrazone

【CA登记号】

【 分 子 式 】C12H14N2O

【 分 子 量 】202.25604

【元素组成】C 71.26% H 6.98% N 13.85% O 7.91%

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:(IX)

By condensation of substituted nicotinamide (VI) with the carbazolyoxymethyl-oxirane (XII) in hot methanol/water. The intermediates the nicotinamide (VI) and the oxirane (XII) have been obtained as follows: 1.- Nicotinamide (VI): The reaction of 4-hydroxybenzyl alcohol (I) with 2-nitropropane (II) by means of potassium tert-butoxide in hot diglyme gives 4-(2-methyl-2-nitropropyl)phenol (III), which is reduced to the corresponding amino derivative (IV) with H2 over Pd/C in methanol/ethanol/acetic acid. Finally, this compound is condensed with 6-chloronicotinamide (V) by means of K2CO3 in dimethylacetamide/isooctane. 2.- Oxirane (XII): The reaction of phenylhydrazine (VII) with cyclohexane-1,3-dione (VIII) by means of NaHCO3 in isopropanol/water gives the monohydrazone (IX), which is cyclized with hotpolyphosphoric acid yielding the 4-hydroxycarbazole (X). Finally, this compound is condensed with the glycidyl 3-nitrophenylsulfonate (XI) by means of K2CO3 in refluxing acetone.

1 Crowell, T.A.; Evrard, D.A.; Jones, C.D.; Muehl, B.S.; Rito, C.J.; Shuker, A.J.; Thorpe, A.J.; Thrasher, K.J. (Eli Lilly and Company); Carbazole analogues as selective B3 adrenergic agonists. EP 0827746; WO 9809625 .
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) 29474 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol 623-05-2 C7H8O2 详情 详情
(II) 21819 2-nitropropane 79-46-9 C3H7NO2 详情 详情
(III) 29475 4-(2-methyl-2-nitropropyl)phenol C10H13NO3 详情 详情
(IV) 29476 4-(2-amino-2-methylpropyl)phenol 51706-55-9 C10H15NO 详情 详情
(V) 29477 6-chloronicotinamide 6271-78-9 C6H5ClN2O 详情 详情
(VI) 29478 6-[4-(2-amino-2-methylpropyl)phenoxy]nicotinamide C16H19N3O2 详情 详情
(VII) 11818 Phenyl hydrazine; 1-Phenylhydrazine 100-63-0 C6H8N2 详情 详情
(VIII) 11244 1,3-Cyclohexanedione 504-02-9 C6H8O2 详情 详情
(IX) 29479 3-hydroxy-2-cyclohexen-1-one N-phenylhydrazone C12H14N2O 详情 详情
(X) 29480 4-Hydroxycarbazole; 9H-carbazol-4-ol 52602-39-8 C12H9NO 详情 详情
(XI) 16259 (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate 115314-14-2 C9H9NO6S 详情 详情
(XII) 29481 9H-carbazol-4-yl (2S)oxiranylmethyl ether; 4-[(2S)oxiranylmethoxy]-9H-carbazole C15H13NO2 详情 详情
Extended Information