• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】21950

【品名】6,7-dichloro-5,8-dimethoxynaphthoquinone

【CA登记号】

【 分 子 式 】C12H8Cl2O4

【 分 子 量 】287.09852

【元素组成】C 50.2% H 2.81% Cl 24.7% O 22.29%

与该中间体有关的原料药合成路线共 4 条

合成路线1

该中间体在本合成路线中的序号:(VI)

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.

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:(VI)

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.

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:(V)

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.

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4

该中间体在本合成路线中的序号:(V)

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.

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