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【结 构 式】 
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【分子编号】47132 【品名】7-hydroxy-5-methoxy-4-methyl-2H-chromen-2-one 【CA登记号】 |
【 分 子 式 】C11H10O4 【 分 子 量 】206.198 【元素组成】C 64.07% H 4.89% O 31.04% |
合成路线1
该中间体在本合成路线中的序号：(I)Condensation of 7-hydroxy-5-methoxy-4-methylcoumarin (I) with 2-chlorocyclohexanone (II) by means of K2CO3 in refluxing acetone affords derivative (III), which is then cyclized by means of refluxing NaOH to provide compound (IV). Oxidation of (IV) by means of DDQ in refluxing benzene furnishes angelicine (V), whose methoxy group is then hydrolyzed with HI and acetic anhydride in refluxing HOAc to yield compound (VI). Finally, the desired product is obtained by coupling of (VI) with 3-chloro-N,N'-dimethylpropylamine (VII) by means of Williamson's reaction using NaH and NaI in refluxing DMF or using K2CO3 and HMPA in refluxing acetone.
| 【1】 Santana, L.; Gia, O.; Dalla Via, L.; Uriarte, E.; A new benzoangelicin with strong photobiological activity. Bioorg Med Chem Lett 2000, 10, 2, 135. |
| 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) | 47132 | 7-hydroxy-5-methoxy-4-methyl-2H-chromen-2-one | C11H10O4 | 详情 | 详情 | |
| (II) | 17985 | 2-Chlorocyclohexanone | 822-87-7 | C6H9ClO | 详情 | 详情 |
| (III) | 47133 | 5-methoxy-4-methyl-7-[(2-oxocyclohexyl)oxy]-2H-chromen-2-one | C17H18O5 | 详情 | 详情 | |
| (IV) | 47134 | 5-methoxy-4-methyl-8,9,10,11-tetrahydro-2H-[1]benzofuro[2,3-h]chromen-2-one | C17H16O4 | 详情 | 详情 | |
| (V) | 47135 | 5-methoxy-4-methyl-2H-[1]benzofuro[2,3-h]chromen-2-one | C17H12O4 | 详情 | 详情 | |
| (VI) | 47136 | 5-hydroxy-4-methyl-2H-[1]benzofuro[2,3-h]chromen-2-one | C16H10O4 | 详情 | 详情 | |
| (VII) | 24581 | 3-(Dimethylamino)propyl chloride; 3-Chloro-N,N-dimethyl-1-propanamine | 5407-04-5 | C5H12ClN | 详情 | 详情 |