【结 构 式】 |
【分子编号】64265 【品名】methyl 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropyl]nicotinate 【CA登记号】 |
【 分 子 式 】C25H31NO2 【 分 子 量 】377.52668 【元素组成】C 79.54% H 8.28% N 3.71% O 8.48% |
合成路线1
该中间体在本合成路线中的序号:(VIII)The Friedel Crafts condensation of 2,5-dichloro-2,2,5,5-tetramethylhexane (I) with toluene (II) by means of AlCl3 gives 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (III), which is submitted to a new condensation with the pyridine-2-carbonyl chloride (IV) by means of AlCl3 in dichloromethane to yield the diaryl ketone (V). The reaction of (V) with methyltriphenylphosphonium bromide (VI) and NaNH2 affords the 1,1-diarylethylene (VII), which is treated with Et2Zn and Cl-CH2-I in dichloromethane to provide the 1,1-diarylcyclopropane (VIII). Finally, the ester group of (VIII) is hydrolyzed with KOH in methanol/water to yield the target carboxylic acid.
【1】 Faul, M.M.; Ratz, A.M.; Sullivan, K.A.; Trankle, W.G.; Winneroski, L.L.; Synthesis of novel retinoid X receptor-selective retinoids. J Org Chem 2001, 66, 17, 5772. |
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) | 35216 | 2,5-dichloro-2,5-dimethylhexane | C8H16Cl2 | 详情 | 详情 | |
(II) | 12890 | Toluene | 108-88-3 | C7H8 | 详情 | 详情 |
(III) | 35217 | 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene | C15H22 | 详情 | 详情 | |
(IV) | 64262 | methyl 6-(chlorocarbonyl)nicotinate | C8H6ClNO3 | 详情 | 详情 | |
(V) | 64263 | methyl 6-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]nicotinate | C23H27NO3 | 详情 | 详情 | |
(VI) | 30484 | Methyl(triphenyl)phosphonium bromide | 1779-49-3 | C19H18BrP | 详情 | 详情 |
(VII) | 64264 | methyl 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)vinyl]nicotinate | C24H29NO2 | 详情 | 详情 | |
(VIII) | 64265 | methyl 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)cyclopropyl]nicotinate | C25H31NO2 | 详情 | 详情 |