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【结 构 式】

【分子编号】21963

【品名】3-(allyloxy)-2,4,5-trifluoro-6-nitrophenyl 4-hydroxybenzoate

【CA登记号】

【 分 子 式 】C16H10F3NO6

【 分 子 量 】369.2537496

【元素组成】C 52.04% H 2.73% F 15.44% N 3.79% O 26%

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:(VI)

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
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