5-amino-6-phenoxy-1-indanone -Drug Synthesis Database

【结构式】

【分子编号】23073

【品名】5-amino-6-phenoxy-1-indanone

【CA登记号】

【分子式】C₁₅H₁₃NO₂

【分子量】239.27376

【元素组成】C 75.3% H 5.48% N 5.85% O 13.37%

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：(X)

1) Condensation of (VII) with tert-butoxybis(dimethylamino)methane followed by ozonolysis of the enamine (VIII) and reduction of the nitro group using Raney Ni yields 5-amino-6-phenoxy-1-indanone (X). In the last step the intermediate (X) is mesylated with mesyl chloride to give CGP 28237.

参考文献中间体

合成目标

【1】 Ferrini, P.G.; Bottcher, I.; CGP-28237. Drugs Fut 1987, 12, 1, 9.
【2】 Schroder, E.; Lehmann, M.; Rufer, C.; Bottcher, I.; Non-steroidal antiinflammatory compounds. 6. Antii. Eur J Med Chem 1982, 17, 1, 35-42.
【3】 Rufer, C.; Bahlmann, F.; Schroder, E.; Bottcher, I.; Non-steroidal antiinflammatory compounds. 8. Antii. Eur J Med Chem 1982, 17, 1, 173-80.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(A)	21487	N-[tert-butoxy(dimethylamino)methyl]-N,N-dimethylamine	C₉H₂₂N₂O	详情	详情
(VII)	23070	6-nitro-2,3-dihydro-1H-inden-5-yl phenyl ether; 5-nitro-6-phenoxyindane	C₁₅H₁₃NO₃	详情	详情
(VIII)	23071	N,N-dimethyl-N-[(5-nitro-6-phenoxy-2,3-dihydro-1H-inden-1-ylidene)methyl]amine; N,N-dimethyl(5-nitro-6-phenoxy-2,3-dihydro-1H-inden-1-ylidene)methanamine	C₁₈H₁₈N₂O₃	详情	详情
(IX)	23072	5-nitro-6-phenoxy-1-indanone	C₁₅H₁₁NO₄	详情	详情
(X)	23073	5-amino-6-phenoxy-1-indanone	C₁₅H₁₃NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(X)

2) Reduction of (VII) using Raney Ni gives 5-amino-6-phenoxyindane (XI), which is acetylated with acetic anhydride and oxidized with CrO3 to yield a mixture of indanones (XII) and (XIII). Chromatographic separation and hydrolysis of (XII) with HCl in ethanol gives 5-amino-6-phenoxy-1-indanone (X), which can be mesylated, as before, to CGP-28237.

参考文献中间体

合成目标

【1】 Ferrini, P.G.; Bottcher, I.; CGP-28237. Drugs Fut 1987, 12, 1, 9.
【2】 Rufer, C.; Bahlmann, F.; Schroder, E.; Bottcher, I.; Non-steroidal antiinflammatory compounds. 8. Antii. Eur J Med Chem 1982, 17, 1, 173-80.
【3】 Schroder, E.; Lehmann, M.; Rufer, C.; Bottcher, I.; Non-steroidal antiinflammatory compounds. 6. Antii. Eur J Med Chem 1982, 17, 1, 35-42.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VII)	23070	6-nitro-2,3-dihydro-1H-inden-5-yl phenyl ether; 5-nitro-6-phenoxyindane	C₁₅H₁₃NO₃	详情	详情
(X)	23073	5-amino-6-phenoxy-1-indanone	C₁₅H₁₃NO₂	详情	详情
(XI)	23075	6-phenoxy-2,3-dihydro-1H-inden-5-ylamine; 6-phenoxy-5-indanamine	C₁₅H₁₅NO	详情	详情
(XII)	23076	N-(1-oxo-6-phenoxy-2,3-dihydro-1H-inden-5-yl)acetamide	C₁₇H₁₅NO₃	详情	详情
(XIII)	23077	N-(3-oxo-6-phenoxy-2,3-dihydro-1H-inden-5-yl)acetamide	C₁₇H₁₅NO₃	详情	详情

Extended Information