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【结 构 式】 
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【分子编号】31619 【品名】4-methyl-N'-[(E)-1-[4-(methylsulfanyl)phenyl]ethylidene]benzenesulfonohydrazide 【CA登记号】 |
【 分 子 式 】C16H18N2O2S2 【 分 子 量 】334.4632 【元素组成】C 57.46% H 5.42% N 8.38% O 9.57% S 19.17% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of 4-(methylsulfanyl)acetophenone (I) with tosylhydrazine by means of PPTS in acetonitrile gives the corresponding hydrazone (II), which by reaction with isopropylmagnesium chloride in THF/toluene yields the vinylmagnesium derivative (III). This compound, without isolation is condensed with 3,5-difluorobenzaldehyde (IV) to afford the allyl alcohol (V), which is condensed with triethyl orthoacetate and saponified providing 5-(3,5-difluorophenyl)-4-[4-(methylsulfanyl)phenyl]-4-pentenoic acid (VI). The cyclization of (VI) with AlCl3 and (COCl)2 in dichloromethane gives the cyclopentenone (VII), which is finally oxidized with potassium peroxymonosulfate (Oxone) in hot acetone/water to afford the target sulfone.
| 【1】 Grabowski, E.J.J.; Zhaol, D.L.; Prasit, P.; Xu, F.; Ouimet, N.; Tillyer, R.D.; Black, C.; Chen, C.Y.; Reider, P.J.; Efficient syntheses of 2-(3 ',5 '-difluorophenyl)-3-(4 '-methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor. Tetrahedron 1999, 55, 19, 6001. |
| 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) | 19262 | 1-[4-(methylsulfanyl)phenyl]-1-ethanone；4'-Methylthioacetophenon；4’-(methylthio)acetophenone | 1778-09-2 | C9H10OS | 详情 | 详情 |
| (II) | 31619 | 4-methyl-N'-[(E)-1-[4-(methylsulfanyl)phenyl]ethylidene]benzenesulfonohydrazide | C16H18N2O2S2 | 详情 | 详情 | |
| (III) | 31620 | chloro[1-[4-(methylsulfanyl)phenyl]vinyl]magnesium | C9H9ClMgS | 详情 | 详情 | |
| (IV) | 31621 | 3,5-difluorobenzaldehyde | 32085-88-4 | C7H4F2O | 详情 | 详情 |
| (V) | 31622 | 1-(3,5-difluorophenyl)-2-[4-(methylsulfanyl)phenyl]-2-propen-1-ol | C16H14F2OS | 详情 | 详情 | |
| (VI) | 31623 | (Z)-5-(3,5-difluorophenyl)-4-[4-(methylsulfanyl)phenyl]-4-pentenoic acid | C18H16F2O2S | 详情 | 详情 | |
| (VII) | 25955 | 2-(3,5-difluorophenyl)-3-[4-(methylsulfanyl)phenyl]-2-cyclopenten-1-one | C18H14F2OS | 详情 | 详情 |