7,8-dihydro-1,6-naphthalenediol -Drug Synthesis Database

【结构式】

【分子编号】22954

【品名】7,8-dihydro-1,6-naphthalenediol

【CA登记号】

【分子式】C₁₀H₁₀O₂

【分子量】162.1882

【元素组成】C 74.06% H 6.21% O 19.73%

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：(I)

The methylation of 1,6-naphthalenediol (I) with dimethyl sulfate gives 1,6-dimethoxynaphthalene (II), which by reaction with sodium-ethanol is converted to 5-methoxy-2-tetralone (III). The condensation of (III) with propylamine - p-toluenesulfonic acid and subsequent hydrogenation with H2 over Pt affords 5-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine (IV). which is demethylated with HBr to 5-hydroxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine (V). Finally, this compound is reductively alkytated with 2-thienylacetic acid (VI) using boranetrimethylamine complex to yield N-0437.

参考文献中间体

合成目标

【1】 Seeman, P.; Horn, A.S.; Grigoriadis, D.; Watanabe, M.; van der Weide, J.; Tepper, P.; Synthesis and radioreceptor binding of N-0437, a n. Pharm Weekbl - Sci Ed 1984, 7, 208.
【2】 Horn, A.S.; N-0437. Drugs Fut 1987, 12, 3, 220.

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)	22954	7,8-dihydro-1,6-naphthalenediol		C₁₀H₁₀O₂	详情	详情
(II)	22955	5-methoxy-3,4-dihydro-2-naphthalenyl methyl ether; 3,8-dimethoxy-1,2-dihydronaphthalene		C₁₂H₁₄O₂	详情	详情
(III)	14647	5-methoxy-3,4-dihydro-2(1H)-naphthalenone	32940-15-1	C₁₁H₁₂O₂	详情	详情
(IV)	14648	N-(5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-propylamine; 5-methoxy-N-propyl-1,2,3,4-tetrahydro-2-naphthalenamine		C₁₄H₂₁NO	详情	详情
(V)	22958	6-(propylamino)-5,6,7,8-tetrahydro-1-naphthalenol		C₁₃H₁₉NO	详情	详情
(VI)	22959	2-(2-thienyl)acetic acid	1918-77-0	C₆H₆O₂S	详情	详情

Extended Information