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【结 构 式】 
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【分子编号】49623 【品名】2,3,5-trimethyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-1,4-benzenediol 【CA登记号】 |
【 分 子 式 】C29H44O2 【 分 子 量 】424.66716 【元素组成】C 82.02% H 10.44% O 7.54% |
合成路线1
该中间体在本合成路线中的序号：(VI)The chlorination of myrcene (I) with Cl2 in refluxing pentane gives the choromyrcene (II), and the hydrochlorination of (I) catalyzed by CuCl yields a mixture of geranyl/neryl chloride (III). The reductive coupling of (II) and (III) by means of Mg and CuCl affords beta-springene (IV), which is condensed with 2,3,6-trimethylhydroquinone (V) by means of cyclooctadienyl rhodium chloride dimer [RhCl(COD)]2 and K2CO3 in refluxing toluene to provide the adduct (VI). The cyclization of (VI) by means of MeAlCl2 of Ts-OH in refluxing hexane furnishes the tocotrienol (VII), which is finally hydrogenated with H2 over Pd/C in ethanol to give the target (rac)-vitamin E.
| 【1】 Bienayme, H.; et al.; Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E. Tetrahedron Lett 2000, 41, 18, 3339. |
| 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) | 49619 | Myrcene; 7-Methyl-3-methylene-1,6-octadiene; beta-Myrcene | 123-35-3 | C10H16 | 详情 | 详情 |
| (II) | 49620 | 3-chloro-2-methyl-6-methylene-1,7-octadiene | C10H15Cl | 详情 | 详情 | |
| (III) | 49621 | Geranyl chloride; trans-1-chloro-3,7-dimethyl-2,6-octadiene | C10H17Cl | 详情 | 详情 | |
| (IV) | 49622 | (6E,10E)-7,11,15-trimethyl-3-methylene-1,6,10,14-hexadecatetraene | C20H32 | 详情 | 详情 | |
| (V) | 26357 | 2,3,5-trimethyl-1,4-benzenediol | 700-13-0 | C9H12O2 | 详情 | 详情 |
| (VI) | 49623 | 2,3,5-trimethyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-1,4-benzenediol | C29H44O2 | 详情 | 详情 | |
| (VII) | 49624 | 2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-6-chromanol | C29H44O2 | 详情 | 详情 |