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【结 构 式】

【分子编号】38483

【品名】2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-2H-chromene; 2,2-dimethyl-2H-chromen-6-yl 4,4,4-trifluorobutyl ether

【CA登记号】

【 分 子 式 】C15H17F3O2

【 分 子 量 】286.2939896

【元素组成】C 62.93% H 5.99% F 19.91% O 11.18%

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:(V)

Chromanone (II) was prepared by reaction of 2',5'-dihydroxyacetophenone (I) with acetone and pyrrolidine. Alkylation of the hydroxyl group of (II) with 4,4,4-trifluorobutyl bromide in the presence of NaH provided ether (III). The keto group of (III) was then reduced to alcohol (IV), which was subsequently dehydrated to chomene (V) by means of p-toluenesulfonic acid in hot toluene. Asymmetric epoxidation of (V) with NaOCl employing the chiral auxiliary (R,R)-bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexane manganese (III) chloride furnished epoxide (VI). Finally, epoxide opening by the sodium salt of N-methyl methanesulfonamide afforded the title compound.

1 Lang, H.J.; Gerlach, U.; Weldmann, K.; Brendel, J. (Aventis Pharma Deutschland GmbH); Sulphonamide substd. benzopyran derivs., process of preparation, their use as medicines and pharmaceutical compsns. containing them. CA 2252733; DE 19748469; EP 0913396; JP 1999222485; US 6008245 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40431 2-[(6aR,9S,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile C17H19N3 详情 详情
40730 1-Bromo-4,4,4-trifluorobutane 1-Bromo-4,4,4-trifluorobutane 406-81-5 C4H6BrF3 详情 详情
(I) 38479 1-(2,5-dihydroxyphenyl)-1-ethanone 490-78-8 C8H8O3 详情 详情
(II) 38480 6-hydroxy-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one C11H12O3 详情 详情
(III) 38481 2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-2,3-dihydro-4H-chromen-4-one C15H17F3O3 详情 详情
(IV) 38482 2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-4-chromanol C15H19F3O3 详情 详情
(V) 38483 2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-2H-chromene; 2,2-dimethyl-2H-chromen-6-yl 4,4,4-trifluorobutyl ether C15H17F3O2 详情 详情
(VI) 38484 (1aR,7bR)-2,2-dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-6-yl 4,4,4-trifluorobutyl ether; (1aR,7bR)-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-1a,7b-dihydro-2H-oxireno[2,3-c]chromene C15H17F3O3 详情 详情
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