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【结 构 式】 
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【分子编号】36035 【品名】1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 【CA登记号】 |
【 分 子 式 】C14H20 【 分 子 量 】188.3128 【元素组成】C 89.3% H 10.7% |
合成路线1
该中间体在本合成路线中的序号：(I)The Friedel Kraft's acylation of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (I) with acetyl chloride by means of AlCl3 in nitrobenzene gives 2-acetyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (II), which is reduced with LiAlH4 in ether yielding 5,6,7,8-tetrahydro-alpha,5,5,8,8-pentamethylnaphthalene-2-methanol (III), The reaction of (III) with PBr3 in ether - hexane affords 2-(1-bromoethyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (IV), which by reaction with triphenylphosphine in hot xylene is converted into [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl]triphenylphosphonium bromide (V). Finally, this compound is submitted to a Wittig condensation with ethyl 4-formylbenzoate (VI) in hot butylene oxide.
| 【1】 Mayer, H.; Loeliger, P.; Bollag, W.; Arotinoids, a new class of highly active retinoids. Eur J Med Chem - Chim Ther 1980, 15, 1, 9-15. |
| 【2】 Loeliger, P. (Hoffmann-La Roche, Inc.); Stilbene derivs.. US 4326055 . |
| 【3】 Blancafort, P.; Hopkins, S.J.; Serradell, M.N.; Castaner, J.; RO-13-6298. Drugs Fut 1983, 8, 5, 432. |
| 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) | 36035 | 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene | C14H20 | 详情 | 详情 | |
| (II) | 36036 | 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-ethanone | C16H22O | 详情 | 详情 | |
| (III) | 36037 | 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-ethanol | C16H24O | 详情 | 详情 | |
| (IV) | 36038 | 6-(1-bromoethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene | C16H23Br | 详情 | 详情 | |
| (V) | 36039 | triphenyl[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethyl]phosphonium bromide | C34H38BrP | 详情 | 详情 | |
| (VI) | 24495 | ethyl 4-formylbenzoate | C10H10O3 | 详情 | 详情 |