1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene -Drug Synthesis Database

【结构式】

【分子编号】60251

【品名】1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene

【CA登记号】

【分子式】C₁₅H₂₀

【分子量】200.3238

【元素组成】C 89.94% H 10.06%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

参考文献中间体

合成目标

【1】 ZhangL.Badea BA, Enyeart D,et aL 1995. Synthesis of isotopically labeled 4{1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydnr2-napluhyl) ethenyl] benzoic aci/l (LGD1069),apotent retinoid Xtecerjtor-se-lective Ligand.J LabeIComp Radiopharm, 36 (7): 701~712

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)	60250	1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydro-2-naphthalenol		C₁₅H₂₂O	详情	详情
(II)	60251	1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene		C₁₅H₂₀	详情	详情
(III)	35217	1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene		C₁₅H₂₂	详情	详情
(IV)	25029	p-Phthalic acid monomethyl ester chloride; Terephthalic acid monomethyl ester chloride; Methyl 4-chlorocarbonylbenzoate	7377-26-6	C₉H₇ClO₃	详情	详情
(V)	35218	methyl 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]benzoate		C₂₄H₂₈O₃	详情	详情
(VI)	60246	methyl 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethenyl]benzoate		C₂₅H₃₀O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The intermediate tetrahydronaththalene (VI) has been prepared by an alternative procedure. Friedel-Crafts condensation of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone (I) with toluene (II) by means of AlCl3 produces tetrahydronaphthalenone (III). This is reduced to alcohol (IV) employing NaBH4 in MeOH. Subsequent dehydration of (IV) with POCl3 in pyridine leads to the dihydronaphthalene (V). Then, catalytic hydrogenation of (V) over Pd/C provides the key pentamethyltetrahydronaphthalene (VI)

参考文献中间体

合成目标

【1】 Zhang, L.; Badea, B.A.; Enyeart, D.; Berger, E.M.; Mais, D.E.; Boehm, M.F.; Syntheses of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid X receptor-selective ligand. J Label Compd Radiopharm 1995, 36, 7, 701.

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)	60248	2,2,5,5-tetramethyldihydro-3(2H)-furanone		C₈H₁₄O₂	详情	详情
(II)	12890	Toluene	108-88-3	C₇H₈	详情	详情
(III)	60249	1,1,4,4,7-pentamethyl-3,4-dihydro-2(1H)-naphthalenone		C₁₅H₂₀O	详情	详情
(IV)	60250	1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydro-2-naphthalenol		C₁₅H₂₂O	详情	详情
(V)	60251	1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene		C₁₅H₂₀	详情	详情
(VI)	35217	1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene		C₁₅H₂₂	详情	详情

Extended Information