【结 构 式】 |
【分子编号】21961 【品名】allyl 2,3,5,6-tetrafluoro-4-nitrophenyl ether; 1-(allyloxy)-2,3,5,6-tetrafluoro-4-nitrobenzene 【CA登记号】 |
【 分 子 式 】C9H5F4NO3 【 分 子 量 】251.1372528 【元素组成】C 43.04% H 2.01% F 30.26% N 5.58% O 19.11% |
合成路线1
该中间体在本合成路线中的序号:(IV)Pentafluoronitrobenzene (I) was reacted with NaNO2 in DMSO to give phenol (II), which was then protected as the allyl ether (IV) upon treatment with allyl bromide (III) and Na2CO3 in refluxing acetone. Further displacement of one fluorine atom of (III) with NaOH under phase transfer conditions afforded phenol (V). This was then attached to a solid phase carboxypolystyrene resin using diisopropyl carbodiimide (DIC) in the presence of pyridine and DMAP. Deprotection of the allyl ether from the resulting resin ester (VI) was accomplished with sodium p-toluenesulfinate and palladium catalyst to yield phenol (VII). The Mitsunobu etherification of phenol (VII) with farnesol (VIII) furnished farnesyl ether (IX). The final product was then cleaved from the resin by treatment with NaOMe in MeOH-THF.
【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261. |
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) | 21958 | 1,2,3,4,5-pentafluoro-6-nitrobenzene | 880-78-4 | C6F5NO2 | 详情 | 详情 |
(II) | 21959 | 2,3,5,6-tetrafluoro-4-nitrophenol | C6HF4NO3 | 详情 | 详情 | |
(IV) | 21961 | allyl 2,3,5,6-tetrafluoro-4-nitrophenyl ether; 1-(allyloxy)-2,3,5,6-tetrafluoro-4-nitrobenzene | C9H5F4NO3 | 详情 | 详情 | |
(V) | 21962 | 3-(allyloxy)-2,4,5-trifluoro-6-nitrophenol | C9H6F3NO4 | 详情 | 详情 | |
(VI) | 21963 | 3-(allyloxy)-2,4,5-trifluoro-6-nitrophenyl 4-hydroxybenzoate | C16H10F3NO6 | 详情 | 详情 | |
(VIII) | 21965 | (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol | 4602-84-0 | C15H26O | 详情 | 详情 |
(IX) | 21966 | 2,4,5-trifluoro-6-nitro-3-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyl]oxy]phenyl 4-hydroxybenzoate | C28H30F3NO6 | 详情 | 详情 |