6-methoxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-ol -Drug Synthesis Database

【结构式】

【分子编号】61071

【品名】6-methoxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-ol

【CA登记号】

【分子式】C₁₃H₁₆O₂

【分子量】204.26884

【元素组成】C 76.44% H 7.9% O 15.67%

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 selective methylation of 5,6,7,8-tetrahydro-5,8-ethanonaphthalene-1,4-diol (I) with dimethylsulfate in a two phase system gives 4-methoxy-5,6,7,8-tetrahydro-5,8-ethano-1-naphthol (II), which is condensed with epichlorohydrin (III) by means of piperidine at 100 C yielding 1-methoxy-4-(2,3-epoxypropoxy)-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (IV). The reaction of (IV) with tert-butylamine (V) at 100 C affords 1-methoxy-4-[3-(tert-butylamino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-5,8-ethanonaphthalene (VI), which is finally demethylated by treatment with pyridine hydrochloride at 160 C

参考文献中间体

合成目标

【1】 Blancafort, P.; Serradell, M.N.; Castaner, J.; McGillion, F.B.; Nafetolol. Drugs Fut 1981, 6, 2, 92.
【2】 Momiyama, N.; Ichikawa, Y.; Hasegawa, S.; Ishikawa, T.; Matsuyama, R.; Miazaki, K.; Shimada, H.; Targeting MMP-7 via antisense oligonucleotide shows anti-metastatic effects in a colon cancer murine model. Eur J Med Chem 1974, 9, 5, 501.

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)	61070	tricyclo[6.2.2.0~2,7~]dodeca-2,4,6-triene-3,6-diol		C₁₂H₁₄O₂	详情	详情
(II)	61071	6-methoxytricyclo[6.2.2.0~2,7~]dodeca-2,4,6-trien-3-ol		C₁₃H₁₆O₂	详情	详情
(III)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(IV)	60172	4,5,6,7-tetrahydro-1H-cyclopenta[a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione		C₁₇H₁₂N₂O₂	详情	详情
(V)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情
(VI)	60173	10-bromo-4,5,6,7-tetrahydro-1H-cyclopenta[a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione		C₁₇H₁₁BrN₂O₂	详情	详情

Extended Information