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【结 构 式】 
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【分子编号】60392 【品名】(E)-1-(5-fluoro-2-hydroxyphenyl)-3-[4-(methylsulfanyl)phenyl]-2-propen-1-one 【CA登记号】 |
【 分 子 式 】C16H13FO2S 【 分 子 量 】288.3424232 【元素组成】C 66.65% H 4.54% F 6.59% O 11.1% S 11.12% |
合成路线1
该中间体在本合成路线中的序号：(III)Aldol condensation between 5'-fluoro-2'-hydroxyacetophenone (I) and 4-(methylthio)benzaldehyde (II) produces chalcone (III). Oxidative cyclization of (III) in hot DMSO in the presence of iodine leads to the flavone compound (IV). Further oxidation of the methylthio group of (IV) employing oxone furnishes sulfone (V). Conversion of flavone (V) into the 3-iodo derivative (VI) is carried out by treatment with iodine and bis(trifluoroacetoxy)iodobenzene. Finally, Suzuki coupling of the iodoflavone (VI) with lithium trimethoxy-3-pyridylboronate (VII) provides the desired 2,3-diaryl benzopyranone
| 【1】 Joo, Y.H.; Kim, J.K.; Kang, S-H.; Noh, M-S.; Ha, J-Y.; Choi, J.K.; Lim, K.M.; Lee, C.H.; Chung, S.; Diarylbenzopyran derivatives as a selective inhibitor of cyclooxygenase-2. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 313. |
| 【2】 Kim, J.K.; Choi, J.K.; Lee, C.H.; Joo, Y.H.; Noh, M.-S.; Ha, J.-Y.; Lim, K.M.; Kang, S.-H. (Pacific Corp.); Diarylbenzopyran derivs. as cyclooxygenase-2 inhibitors. EP 1105384; JP 2002523410; US 6340694; WO 0010993 . |
| 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) | 60391 | 1-(5-fluoro-2-hydroxyphenyl)-1-ethanone | 394-32-1 | C8H7FO2 | 详情 | 详情 |
| (II) | 18815 | 4-(methylsulfanyl)benzaldehyde; 4-(methylmercapto)benzaldehyde | 3446-89-7 | C8H8OS | 详情 | 详情 |
| (III) | 60392 | (E)-1-(5-fluoro-2-hydroxyphenyl)-3-[4-(methylsulfanyl)phenyl]-2-propen-1-one | C16H13FO2S | 详情 | 详情 | |
| (IV) | 60393 | 6-fluoro-2-[4-(methylsulfanyl)phenyl]-4H-chromen-4-one | C16H11FO2S | 详情 | 详情 | |
| (V) | 60394 | 6-fluoro-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one | C16H11FO4S | 详情 | 详情 | |
| (VI) | 60395 | 6-fluoro-3-iodo-2-[4-(methylsulfonyl)phenyl]-4H-chromen-4-one | C16H10FIO4S | 详情 | 详情 | |
| (VII) | 30006 | Trimethoxy(3-pyridyl)boranuide lithium salt | C8H13BLiNO3 | 详情 | 详情 |