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【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%

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:(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
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