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【结 构 式】 
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【药物名称】HI-D12, WHI-D12 【化学名称】5-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2,8-dihydropyrano[2,3-f]-1-benzopyran-8-one 【CA登记号】 【 分 子 式 】C20H22O5 【 分 子 量 】342.39534 |
【开发单位】Parker Hughes Institute (Originator) 【药理作用】ONCOLYTIC DRUGS, Bruton's Tyrosine Kinase (BTK) Kinase Inhibitors , Inhibitors of Signal Transduction Pathways |
合成路线1
The cyclization of floroglucinol (I) with ethyl 2-oxohexanoate (II) in acidic medium gives 5,7-dihydroxy-4-propyl-2H-1-benzopyran-2-one (III), which is submitted to a Friedel Crafts condensation with propionyl chloride (IV) / AlCl3 to yield the 8-propionyl derivative (V). Finally, the cyclization of (V) with 3-hydroxy-3-methylbutyraldehyde dimethyl acetal (VI) in refluxing pyridine affords the target compound.
| 【1】 Sudbeck, E.A.; Uckun, F.M. (Parker Hughes Institute); Calanolides for inhibiting BTK. WO 0056737 . |
| 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) | 11799 | 1,3,5-Benzenetriol; Fluoroglucinol | 108-73-6 | C6H6O3 | 详情 | 详情 |
| (II) | 12516 | ethyl 3-oxohexanoate; ethyl butyrylacetate | 3249-68-1 | C8H14O3 | 详情 | 详情 |
| (III) | 22405 | 5,7-dihydroxy-4-propyl-2H-chromen-2-one | C12H12O4 | 详情 | 详情 | |
| (IV) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
| (V) | 22407 | 5,7-dihydroxy-8-propionyl-4-propyl-2H-chromen-2-one | C15H16O5 | 详情 | 详情 | |
| (VI) | 22408 | 4,4-dimethoxy-2-methyl-2-butanol | C7H16O3 | 详情 | 详情 |
Extended Information