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【结 构 式】 
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【药物名称】 【化学名称】2-Chloro-3,5,8-trimethoxy-1,4-naphthalenedione 【CA登记号】 【 分 子 式 】C13H11ClO5 【 分 子 量 】282.68262 |
【开发单位】China Medical College (Originator), National Taiwan University (Originator), University of North Carolina (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Antiplatelet Therapy, Asthma Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, RESPIRATORY DRUGS, Antiinflammatory Drugs |
合成路线1
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 |