1,4-anthracenediol -Drug Synthesis Database

【结构式】

【分子编号】53469

【品名】1,4-anthracenediol

【CA登记号】7218-35-1

【分子式】C₁₄H₁₀O₂

【分子量】210.2322

【元素组成】C 79.98% H 4.79% O 15.22%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(III)

The reduction of 1,4-dihydroxy-9,10-anthraquinone (I) with NaBH4 in methanol gives 1,4-anthraquinone (II), which is reduced with Na2S2O4 in dioxane/water to yield 1,4-anthracenediol (III). The methylation of (III) with NaH and Me-I in DMF affords 1,4-dimethoxyanthracene (IV), which is condensed with 2-methoxy-1,4-benzoquinone (V) (obtained by oxidation of 2-methoxyhydroquinone (VI) with Ag2O and K2CO3 in benzene) by heating at 150 C with toluene in a sealed tube to provide the triptycene derivative (VII). The reaction of (VII) with KOH in dioxane/water gives the triptycenediol (VIII), which is oxidized with Ag2O in refluxing acetone to yield the triptycenequinone (IX). Finally, this compound is oxidized with Ce(NH4)2(NO3)6 to afford the target triptycenediquinone.

参考文献中间体

合成目标

【1】 Hua, D.H.; Perchellet, J.-P. (Kansas State University); Triptycene analogs. WO 0228808 .

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)	53467	1,4-Dihydroxy-9,10-anthracenedione; 1,4-Dihydroxyanthraquinone; Chinizarin; Quinazarin; Quinizarin	81-64-1	C₁₄H₈O₄	详情	详情
(II)	53468	1,4-Anthracenedione; 1,4-Anthraquinone	635-12-1	C₁₄H₈O₂	详情	详情
(III)	53469	1,4-anthracenediol	7218-35-1	C₁₄H₁₀O₂	详情	详情
(IV)	53470	1,4-dimethoxyanthracene; 4-methoxy-1-anthryl methyl ether	13076-29-4	C₁₆H₁₄O₂	详情	详情
(V)	53471	Methoxybenzoquinone	2880-58-2	C₇H₆O₃	详情	详情
(VI)	16845	2-methoxy-1,4-benzenediol	824-46-4	C₇H₈O₃	详情	详情
(VII)	53472	4,10,13-trimethoxypentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-4,9,11,13,15,17,19-heptaene-3,6-dione	n/a	C₂₃H₂₀O₅	详情	详情
(VIII)	53473	4,10,13-trimethoxypentacyclo[6.6.6.0^2,7.0^9,14.0^15,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-3,6-diol	n/a	C₂₃H₂₀O₅	详情	详情
(IX)	53474	4,10,13-trimethoxypentacyclo[6.6.6.0^2,7.0^9,14.0^15,20]icosa-2(7),4,9,11,13,15,17,19-octaene-3,6-dione	n/a	C₂₃H₁₈O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reduction of 1,4-dihydroxy-9,10-anthraquinone (I) with NaBH4 in methanol gives 1,4-anthraquinone (II), which is reduced with Na2S2O4 in dioxane/water to yield 1,4-anthracenediol (III). The methylation of (III) with NaH and Me-I in DMF affords 1,4-dimethoxyanthracene (IV), which is condensed with 2-methoxy-1,4-benzoquinone (V) (obtained by oxidation of 2-methoxyhydroquinone (VI) with Ag2O and K2CO3 in benzene) by heating at 150 C with toluene in a sealed tube to provide the triptycene derivative (VII). The reaction of (VII) with KOH in dioxane/water gives the triptycenediol (VIII), which is oxidized with Ag2O in refluxing acetone to yield the triptycenequinone (IX). The bromination of (IX) with NBS in hot DMF affords the bromo derivative (X), which is finally oxidized with Ce(NH4)2(NO3)6 to afford the target triptycenediquinone.

参考文献中间体

合成目标

【1】 Hua, D.H.; Perchellet, J.-P. (Kansas State University); Triptycene analogs. WO 0228808 .

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)	53467	1,4-Dihydroxy-9,10-anthracenedione; 1,4-Dihydroxyanthraquinone; Chinizarin; Quinazarin; Quinizarin	81-64-1	C₁₄H₈O₄	详情	详情
(II)	53468	1,4-Anthracenedione; 1,4-Anthraquinone	635-12-1	C₁₄H₈O₂	详情	详情
(III)	53469	1,4-anthracenediol	7218-35-1	C₁₄H₁₀O₂	详情	详情
(IV)	53470	1,4-dimethoxyanthracene; 4-methoxy-1-anthryl methyl ether	13076-29-4	C₁₆H₁₄O₂	详情	详情
(V)	53471	Methoxybenzoquinone	2880-58-2	C₇H₆O₃	详情	详情
(VI)	16845	2-methoxy-1,4-benzenediol	824-46-4	C₇H₈O₃	详情	详情
(VII)	53472	4,10,13-trimethoxypentacyclo[6.6.6.0~2,7~.0~9,14~.0~15,20~]icosa-4,9,11,13,15,17,19-heptaene-3,6-dione	n/a	C₂₃H₂₀O₅	详情	详情
(VIII)	53473	4,10,13-trimethoxypentacyclo[6.6.6.0^2,7.0^9,14.0^15,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-3,6-diol	n/a	C₂₃H₂₀O₅	详情	详情
(IX)	53474	4,10,13-trimethoxypentacyclo[6.6.6.0^2,7.0^9,14.0^15,20]icosa-2(7),4,9,11,13,15,17,19-octaene-3,6-dione	n/a	C₂₃H₁₈O₅	详情	详情
(X)	53475	4-bromo-5,10,13-trimethoxypentacyclo[6.6.6.0^2,7.0^9,14.0^15,20]icosa-2(7),4,9,11,13,15,17,19-octaene-3,6-dione	n/a	C₂₃H₁₇BrO₅	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

Reduction of quinizarin (I) with NaBH4 in MeOH, followed by quenching with HCl provides 1,4-anthraquinone (II). This is further reduced to 1,4-dihydroxyanthracene (III) employing sodium hydrosulfite in dioxane. Subsequent methylation of diol (III) with iodomethane and NaH leads to the key intermediate 1,4-dimethoxyanthracene (IV).

参考文献中间体

合成目标

【1】 Hua, D.H.; et al.; Syntheses and bioactivities of substituted 9,10-dihydro-9,10[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines. J Org Chem 2002, 67, 9, 2907.

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)	53467	1,4-Dihydroxy-9,10-anthracenedione; 1,4-Dihydroxyanthraquinone; Chinizarin; Quinazarin; Quinizarin	81-64-1	C₁₄H₈O₄	详情	详情
(II)	53468	1,4-Anthracenedione; 1,4-Anthraquinone	635-12-1	C₁₄H₈O₂	详情	详情
(III)	53469	1,4-anthracenediol	7218-35-1	C₁₄H₁₀O₂	详情	详情
(IV)	53470	1,4-dimethoxyanthracene; 4-methoxy-1-anthryl methyl ether	13076-29-4	C₁₆H₁₄O₂	详情	详情

Extended Information