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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information