• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】27268

【品名】4,4-dimethyl-7-nitro-3,4-dihydro-1(2H)-naphthalenone

【CA登记号】

【 分 子 式 】C12H13NO3

【 分 子 量 】219.24016

【元素组成】C 65.74% H 5.98% N 6.39% O 21.89%

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:(IV)

Ethyl levulinate (I) was reacted with one equivalent of methylmagnesium bromide to produce 5,5-dimethyldihydrofuran-2-one (II). Friedel-Crafts condensation of (III) with benzene in the presence of AlCl3 afforded 4,4-dimethyl-1-tetralone (III) which, after nitration and reduction furnished the aminotetralone (V). This was converted to iodide (VI) upon diazotization, followed by treatment with KI. Methyl 4-vinylbenzoate (VIII) was obtained by alkylation of the corresponding carboxylic acid (VII) with MeI in the presence of DBU. Coupling of this olefin (VIII) with iodide (VI) was carried out using palladium diacetate and tetrabutylammonium chloride at 70 C to yield the diaryl ethylene derivative (IX). Subsequent addition of phenylmagnesium bromide to (IX) produced the tertiary alcohol (X). Finally, dehydration of (X) using p-toluenesulfonic acid, followed by basic hydrolysis, provided the title compound.

1 Starrett, J.E. Jr.; Yu, K.-L.; Mansuri, M.M.; Tortolani, D.R. (Bristol-Myers Squibb Co.); Substd. (5,6)-dihydronaphthalenyl cpds. having retinoid-like activity. CA 2138000; EP 0661259; JP 1995242591; US 5648385 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
17616 bromo(phenyl)magnesium; Phenyl Magnesium Bromide 100-58-3 C6H5BrMg 详情 详情
(I) 27267 ethyl 4-oxopentanoate 539-88-8 C7H12O3 详情 详情
(II) 23768 5,5-dimethyldihydro-2(3H)-furanone C6H10O2 详情 详情
(III) 23791 4,4-dimethyl-3,4-dihydro-1(2H)-naphthalenone 2979-69-3 C12H14O 详情 详情
(IV) 27268 4,4-dimethyl-7-nitro-3,4-dihydro-1(2H)-naphthalenone C12H13NO3 详情 详情
(V) 27269 7-amino-4,4-dimethyl-3,4-dihydro-1(2H)-naphthalenone C12H15NO 详情 详情
(VI) 27270 7-iodo-4,4-dimethyl-3,4-dihydro-1(2H)-naphthalenone C12H13IO 详情 详情
(VII) 27271 4-vinylbenzoic acid 1075-49-6 C9H8O2 详情 详情
(VIII) 27272 methyl 4-vinylbenzoate C10H10O2 详情 详情
(IX) 27273 methyl 4-[(E)-2-(5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-2-naphthalenyl)ethenyl]benzoate C22H22O3 详情 详情
(X) 27274 methyl 4-[(E)-2-(8-hydroxy-5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethenyl]benzoate C28H28O3 详情 详情
Extended Information