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【结 构 式】

【分子编号】49069

【品名】1,1-dibromo-4,4-dimethyl-1,7-octadiene

【CA登记号】

【 分 子 式 】C10H16Br2

【 分 子 量 】296.04504

【元素组成】C 40.57% H 5.45% Br 53.98%

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:(XXV)

Alternatively, the intermediate (Z)-ethylenic diol (XV) can also be obtained as follows: The reduction of 5,5-dimethyloxepan-2-one (XX) with iBu2AlH in THF gives 5,5-dimethyloxepan-2-ol (XXI), which is condensed with methyltriphenylphosphonium bromide (XXII) by means of tBu-OK in THF to yield 3,3-dimethyl-6-hepten-1-ol (XXIII). The Swern oxidation of the primary alcohol of (XIII) affords aldehyde (XXIV), which is condensed with CBr4 by means of PPh3 in CH2Cl2 to provide the dibromovinyl compound (XXV). The condensation of (XXV) with hexafluoroacetone (XII) by means of BuLi gives the acetylenic alcohol (XXVI), which is treated with hexylborane in THF to yield the acetylenic diol (XXVII). Finally, this compound is selectively reduced with H2 over Pd/C in EtOAc to afford the desired (Z)-ethylenic diol (XV).

1 Mohr, P.; Barbier, P.; Pirson, W.; Muller, M.; Bauer, F. (F. Hoffmann-La Roche AG); Cyclohexanediole derivs.. EP 1056716; WO 9943646 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 44260 1,1,1,3,3,3-hexafluoroacetone 684-16-2 C3F6O 详情 详情
(XV) 49036 (Z)-10,10,10-trifluoro-5,5-dimethyl-9-(trifluoromethyl)-7-decene-1,9-diol C13H20F6O2 详情 详情
(XX) 49065 5,5-dimethyl-2-oxepanone C8H14O2 详情 详情
(XXI) 49066 5,5-dimethyl-2-oxepanol C8H16O2 详情 详情
(XXII) 30484 Methyl(triphenyl)phosphonium bromide 1779-49-3 C19H18BrP 详情 详情
(XXIII) 49067 3,3-dimethyl-6-hepten-1-ol C9H18O 详情 详情
(XXIV) 49068 3,3-dimethyl-6-heptenal C9H16O 详情 详情
(XXV) 49069 1,1-dibromo-4,4-dimethyl-1,7-octadiene C10H16Br2 详情 详情
(XXVI) 49070 1,1,1-trifluoro-6,6-dimethyl-2-(trifluoromethyl)-9-decen-3-yn-2-ol C13H16F6O 详情 详情
(XXVII) 49062 10,10,10-trifluoro-5,5-dimethyl-9-(trifluoromethyl)-7-decyne-1,9-diol C13H18F6O2 详情 详情
Extended Information