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【结 构 式】 
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【分子编号】19270 【品名】3-iodo-4-[4-(methylsulfanyl)phenyl]-2(5H)-furanone 【CA登记号】 |
【 分 子 式 】C11H9IO2S 【 分 子 量 】332.16173 【元素组成】C 39.78% H 2.73% I 38.21% O 9.63% S 9.65% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)6) The reaction of 4-bromothioanisole (XIV) with furan-2(5H)-one (XV) by means of tert-BuLi/CuI in ethyl ether, followed by silylation with trimethylsilyl chloride gives 4-[4-(methylsulfanyl)phenyl]-2-(trimethylsilyloxy)-3,4-dihydrofuran (XVI), which is desilylated with palladium acetate in acetonitrile to afford the furanone (XVII). The iodination of (XVII) with I2 in pyridine yields 3-iodo-4-[4-(methylsulfanyl)phenyl]furan-2(5H)-one (XVIII), which is condensed with phenylboronic acid (XIX) by means of triphenylarsine and a Pd catalyst in refluxing benzene, giving 4-[4-(methylsulfanyl)phenyl]-3-phenylfuran-2(5H)-one (VIII), already described in Scheme 1. Finally, this compound is oxidized with monoperoxyphthalic acid magnesium salt in dichloromethane/methanol.
| 【1】 Sorbera, L.A.; Rabasseda, X.; Castañer, J.; Rofecoxib. Drugs Fut 1998, 23, 12, 1287. |
| 【2】 Atkinson, J.G.; Wang, Z. (Merck Frosst Canada Inc.); Stilbene derivs. useful as cyclooxygenase-2 inhibitors. EP 0788476; JP 1998507765; WO 9613483 . |
| 【3】 Hancock, B.; Winters, C.; Gertz, B.; Ehrich, E. (Merck & Co., Inc.; Merck Frosst Canada Inc.); Compsns. for a once a day treatment of cyclooxygenase-2 mediated diseases. JP 1999512754; WO 9744028 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 19260 | 4-[4-(methylsulfanyl)phenyl]-3-phenyl-2(5H)-furanone | C17H14O2S | 详情 | 详情 | |
| (XIV) | 19266 | 4-bromophenyl methyl sulfide; 1-bromo-4-(methylsulfanyl)benzene | 104-95-0 | C7H7BrS | 详情 | 详情 |
| (XV) | 19267 | 2(5H)-furanone；furan-2(5H)-one；2-Buten-1,4-olide | 497-23-4 | C4H4O2 | 详情 | 详情 |
| (XVI) | 19268 | trimethyl([4-[4-(methylsulfanyl)phenyl]-4,5-dihydro-2-furanyl]oxy)silane; 4-[4-(methylsulfanyl)phenyl]-4,5-dihydro-2-furanyl trimethylsilyl ether | C14H20O2SSi | 详情 | 详情 | |
| (XVII) | 19269 | 4-[4-(methylsulfanyl)phenyl]-2(5H)-furanone | C11H10O2S | 详情 | 详情 | |
| (XVIII) | 19270 | 3-iodo-4-[4-(methylsulfanyl)phenyl]-2(5H)-furanone | C11H9IO2S | 详情 | 详情 | |
| (XIX) | 16593 | Phenylboronic acid；Benzeneboronic acid;Phenylboron dihydroxide | 98-80-6 | C6H7BO2 | 详情 | 详情 |