【结 构 式】 |
【分子编号】32531 【品名】3-(tributylstannyl)phenyl acetate 【CA登记号】 |
【 分 子 式 】C20H34O2Sn 【 分 子 量 】425.19876 【元素组成】C 56.5% H 8.06% O 7.53% Sn 27.92% |
合成路线1
该中间体在本合成路线中的序号:(XVI)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), which was converted to vinyl triflate (XV) by means of trifluoromethanesulfonic anhydride and 2,6-di-tert-butyl-4-methylpyridine (DTBMP). Diaryl anthracene (XVII) was prepared by Stille coupling of triflate (XV) with 3-acetoxytributylstannylbenzene (XVI). Finally, the title carboxylic acid was obtained by saponification of both ester groups of (XVII) by means of 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) | 32531 | 3-(tributylstannyl)phenyl acetate | C20H34O2Sn | 详情 | 详情 | |
(XVII) | 32532 | methyl 4-[8-[3-(acetoxy)phenyl]-5,5-dimethyl-5,6-dihydro-2-anthracenyl]benzoate | C32H28O4 | 详情 | 详情 |