2,3-dichloro-5,8-dihydroxynaphthoquinone -Drug Synthesis Database

【结构式】

【分子编号】21948

【品名】2,3-dichloro-5,8-dihydroxynaphthoquinone

【CA登记号】14918-69-5

【分子式】C₁₀H₄Cl₂O₄

【分子量】259.04476

【元素组成】C 46.37% H 1.56% Cl 27.37% O 24.71%

与该中间体有关的原料药合成路线共 7 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7

合成路线1

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded a dihydroxynaphthoquinone, assumed to exist as an equilibrium mixture between posicional isomers (III) and (IV). Subsequent methylation with CH3I in the presence of Ag2O yielded a mixture of dimethoxy quinones (V) and (VI) from which the target compound (V) was isolated by column chromatography.

参考文献中间体

合成目标

【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21949	6,7-dichloro-5,8-dihydroxynaphthoquinone		C₁₀H₄Cl₂O₄	详情	详情
(VI)	21950	6,7-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded a dihydroxynaphthoquinone, assumed to exist as an equilibrium mixture between posicional isomers (III) and (IV). Subsequent methylation with CH3I in the presence of Ag2O yielded a mixture of dimethoxy quinones (V) and (VI), which were separated by column chromatography. Treatment of isomer (V) with NaOMe in MeOH then produced the target trimethoxy quinone.

参考文献中间体

合成目标

【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21949	6,7-dichloro-5,8-dihydroxynaphthoquinone		C₁₀H₄Cl₂O₄	详情	详情
(V)	21951	2,3-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(VI)	21950	6,7-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21949	6,7-dichloro-5,8-dihydroxynaphthoquinone		C₁₀H₄Cl₂O₄	详情	详情
(V)	21951	2,3-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情

合成路线4

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dihydroxynaphthoquinone (III). Subsequent acetylation with Ac2O and AcOH furnished the target diacetate.

参考文献中间体

合成目标

【1】 Huang, L.-J.; Chang, F.C.; Lee, K.H.; Wang, J.P; Teng, C.M.; Kuo, S.C.; Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds. Bioorg Med Chem 1998, 6, 12, 2261.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情

合成路线5

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III). Finally, treatment of (III) with resorcinol (IV) and Na2CO3 in DMSO at room temperature furnished the target compound.

参考文献中间体

合成目标

【1】 Chang, H.-X.; Chou, T.C.; Savaraj, N.; Liu, L.F.; Yu, C.; Cheng, C.C.; Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones. J Med Chem 1999, 42, 3, 405.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	10361	1,3-Dihydroxybenzene; m-Dihydroxybenzene; Resorcinol; Resorcin; 1,3-Benzenediol	108-46-3	C₆H₆O₂	详情	详情

合成路线6

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III). Subsequent methylation of (III) with CH3I in the presence of Ag2O in CHCl3 gave a mixture of dimethoxy naphthoquinones (IV) and (V), from which the desired isomer (IV) was isolated by recrystallization from CHCl3-CCl4. Finally, treatment of (IV) with 3-methoxyphenol (VI) and Na2CO3 in DMSO at room temperature furnished the target compound.

参考文献中间体

合成目标

【1】 Chang, H.-X.; Chou, T.C.; Savaraj, N.; Liu, L.F.; Yu, C.; Cheng, C.C.; Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones. J Med Chem 1999, 42, 3, 405.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21951	2,3-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(V)	21950	6,7-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(VI)	22389	3-Methoxyphenol	150-19-6	C₇H₈O₂	详情	详情

合成路线7

该中间体在本合成路线中的序号：(III)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III). Subsequent methylation of (III) with CH3I in the presence of Ag2O in CHCl3 gave a mixture of dimethoxy naphthoquinones (IV) and (V), from which the desired isomer (IV) was isolated by recrystallization from CHCl3-CCl4. Finally, treatment of (IV) with 3,5-dimethoxyphenol (VI) and Na2CO3 in DMSO at room temperature furnished the target compound.

参考文献中间体

合成目标

【1】 Chang, H.-X.; Chou, T.C.; Savaraj, N.; Liu, L.F.; Yu, C.; Cheng, C.C.; Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones. J Med Chem 1999, 42, 3, 405.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21951	2,3-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(V)	21950	6,7-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(VI)	22390	3,5-dimethoxyphenol	500-99-2	C₈H₁₀O₃	详情	详情

Extended Information