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【结 构 式】 
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【分子编号】32530 【品名】tributyl(3-methylphenyl)stannane 【CA登记号】 |
【 分 子 式 】C19H34Sn 【 分 子 量 】381.18896 【元素组成】C 59.87% H 8.99% Sn 31.14% |
合成路线1
该中间体在本合成路线中的序号：(XIX)Triflate (XI) was coupled with methyl 4-(tributylstannyl)benzoate (XII) using Pd2(dba)3 and Ph3As to introduce the benzoate side-chain yielding (XIII). Benzylic oxidation of (XIII) with tert-butyl hydroperoxide and pyridinium dichromate provided anthracenone (XIV). Optionally, this was converted to vinyl triflate (XV) by means of trifluoromethanesulfonic anhydride and 2,6-di-tert-butyl-4-methylpyridine (DTBMP). Addition of Grignard reagent (XVI) to ketone (XIV), followed by acid dehydration of the resulting carbinol (XVIII) furnished the diaryl anthracene (XVIII). In an alternative procedure intermediate (XVIII) was prepared by Stille coupling of vinyl triflate (XV) with 3-methyl tributylstannylbenzene (XIX). Finally, the title carboxylic acid was obtained by saponification of the ester group of (XIX) with KOH.
| 【1】 Ericsson, A.; Marinier, A.; Lapointe, P.; et al.; Synthesis and SAR of novel dihydroanthracene derivatives as retinoid analogs. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 43. |
| 【2】 Starrett, J.E. Jr.; Tramposch, K.M.; Martel, A.; Nair, X.; Zusi, F.C.; Reczek, P.R.; Marinier, A.; Ericsson, A. (Bristol-Myers Squibb Co.); Retinoid-like cpds.. WO 9849136 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 32522 | 5,5-dimethyl-5,6,7,8-tetrahydro-2-anthracenyl trifluoromethanesulfonate | C17H17F3O3S | 详情 | 详情 | |
| (XII) | 32523 | methyl 4-(tributylstannyl)benzoate | C20H34O2Sn | 详情 | 详情 | |
| (XIII) | 32524 | methyl 4-(5,5-dimethyl-5,6,7,8-tetrahydro-2-anthracenyl)benzoate | C24H24O2 | 详情 | 详情 | |
| (XIV) | 32525 | methyl 4-(5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-2-anthracenyl)benzoate | C24H22O3 | 详情 | 详情 | |
| (XV) | 32526 | methyl 4-(5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-5,6-dihydro-2-anthracenyl)benzoate | C25H21F3O5S | 详情 | 详情 | |
| (XVI) | 32527 | bromo(3-methylphenyl)magnesium | C7H7BrMg | 详情 | 详情 | |
| (XVII) | 32528 | methyl 4-[8-hydroxy-5,5-dimethyl-8-(3-methylphenyl)-5,6,7,8-tetrahydro-2-anthracenyl]benzoate | C31H30O3 | 详情 | 详情 | |
| (XVIII) | 32529 | methyl 4-[5,5-dimethyl-8-(3-methylphenyl)-5,6-dihydro-2-anthracenyl]benzoate | C31H28O2 | 详情 | 详情 | |
| (XIX) | 32530 | tributyl(3-methylphenyl)stannane | C19H34Sn | 详情 | 详情 |