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【结 构 式】

【分子编号】39579

【品名】3-[(E)-5-hydroxy-3-methyl-3-penten-1-ynyl]-2,4,4-trimethyl-2-cyclohexen-1-one

【CA登记号】

【 分 子 式 】C15H20O2

【 分 子 量 】232.3226

【元素组成】C 77.55% H 8.68% O 13.77%

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:(V)

The reaction of 3-methyl-2-trans-penten-4-yn-1-ol (I) with ethyl vinyl ether (II) by means of p-toluenesulfonic acid gives 1-(1-ethoxyethoxy)-3-methyl-4-trans-penten-1-yne (III), which is condensed with 2,6,6-trimethyl-3-isobutoxycyclohex-2-en-1-one (IV) by means of butyllithium in ether at -60 C to afford 5-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methyl-2-trans-penten-4-yn-1-ol (V). The reduction of (V) with H2 over a Lindlar catalyst in toluene yields 5-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol (VI), which is converted into the corresponding pentadienyl bromide (VII) by reaction with PBr3 in ether. The reaction of (VII) with triphenylphosphine in refluxing benzene affords 5-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methyl-2,4-pentadien-1-triphenylphosphonium bromide (VIII) , which is finally condensed in a Wittig reaction with 2,7-dimethyl-2,4,6-octatriene-1,8-dial (IX) by means of sodium methoxide in dichloromethane.

1 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477.
2 Rosenberg, M.; US 4000198 .
3 Rigassi, N.; Schwieter, U.; DE 2037935 .
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) 39576 (E)-3-methyl-2-penten-4-yn-1-ol 6153-06-6 C6H8O 详情 详情
(II) 18762 1-Ethoxyethylene; Ethyl vinyl ether;Ethoxyethene 109-92-2 C4H8O 详情 详情
(III) 39577 5-(1-ethoxyethoxy)-3-methyl-1-penten-4-yne; 1-ethoxyethyl 3-methyl-4-penten-1-ynyl ether C10H16O2 详情 详情
(IV) 39578 3-isobutoxy-2,6,6-trimethyl-2-cyclohexen-1-one C13H22O2 详情 详情
(V) 39579 3-[(E)-5-hydroxy-3-methyl-3-penten-1-ynyl]-2,4,4-trimethyl-2-cyclohexen-1-one C15H20O2 详情 详情
(VI) 39580 3-[(1E,3E)-5-hydroxy-3-methyl-1,3-pentadienyl]-2,4,4-trimethyl-2-cyclohexen-1-one 29538-78-1 C15H22O2 详情 详情
(VII) 39581 3-[(1E,3E)-5-bromo-3-methyl-1,3-pentadienyl]-2,4,4-trimethyl-2-cyclohexen-1-one C15H21BrO 详情 详情
(VIII) 39582 [(2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienyl](triphenyl)phosphonium bromide C33H36BrOP 详情 详情
(IX) 39583 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial C10H12O2 详情 详情
Extended Information