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【结 构 式】 
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【分子编号】19274 【品名】2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate 【CA登记号】 |
【 分 子 式 】C17H16O5S 【 分 子 量 】332.37704 【元素组成】C 61.43% H 4.85% O 24.07% S 9.65% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(XXII)7) The Friedel-Crafts condensation of thioanisole (XX) with acetyl chloride (XXI) by means of AlCl3 in dichlorobenzene gives the corresponding acetophenone (X), which is oxidized with H2O2/WO4Na2 to the ketosulfone (XI). The bromination of (XI) with Br2 in acetic acid/48% HBr affords the phenacyl bromide (XII), which is condensed with phenylacetic acid sodium salt (XXIII) in DMF, giving the phenacyl ester (XXII). Finally, this compound is cyclized by means of diisopropylamine in DMF.
| 【1】 Sorbera, L.A.; Rabasseda, X.; Castañer, J.; Rofecoxib. Drugs Fut 1998, 23, 12, 1287. |
| 【2】 Frey, L.F.; Dolling, U.H.; Desmond, R.; Tillyer, R.D.; Tschaen, D.M. (Merck & Co., Inc.); Process of preparing phenyl heterocycles useful as COX-2 inhibitors. WO 9800416 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 19262 | 1-[4-(methylsulfanyl)phenyl]-1-ethanone；4'-Methylthioacetophenon；4’-(methylthio)acetophenone | 1778-09-2 | C9H10OS | 详情 | 详情 |
| (XI) | 19263 | 1-[4-(methylsulfonyl)phenyl]-1-ethanone; 4-methylsulfonylacetophenone | 10297-73-1 | C9H10O3S | 详情 | 详情 |
| (XII) | 19264 | 2-bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone | C9H9BrO3S | 详情 | 详情 | |
| (XX) | 19272 | methyl phenyl sulfide; 1-(methylsulfanyl)benzene | 100-68-5 | C7H8S | 详情 | 详情 |
| (XXI) | 19273 | acetyl chloride | 75-36-5 | C2H3ClO | 详情 | 详情 |
| (XXII) | 19274 | 2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate | C17H16O5S | 详情 | 详情 | |
| (XXIII) | 19275 | sodium 2-phenylacetate | 114-70-5 | C8H7NaO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)
| 【1】 Sharma NR.Rawat GS. 2004. Synthesis of rofecoxib and study of Lactone ring stability. Asia J Chem, 16: 978～982 |
| 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) | 19263 | 1-[4-(methylsulfonyl)phenyl]-1-ethanone; 4-methylsulfonylacetophenone | 10297-73-1 | C9H10O3S | 详情 | 详情 |
| (III) | 19264 | 2-bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone | C9H9BrO3S | 详情 | 详情 | |
| (IV) | 16148 | Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid | 103-82-2 | C8H8O2 | 详情 | 详情 |
| (V) | 19274 | 2-[4-(methylsulfonyl)phenyl]-2-oxoethyl 2-phenylacetate | C17H16O5S | 详情 | 详情 |
Extended Information