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【结 构 式】 
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【分子编号】38484 【品名】(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 【CA登记号】 |
【 分 子 式 】C15H17F3O3 【 分 子 量 】302.2933896 【元素组成】C 59.6% H 5.67% F 18.85% O 15.88% |
合成路线1
该中间体在本合成路线中的序号：(VI)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 |