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【结 构 式】 
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【分子编号】58851 【品名】4,8-dimethyl-7-(1-methyl-2-oxopropoxy)-2H-chromen-2-one 【CA登记号】 |
【 分 子 式 】C15H16O4 【 分 子 量 】260.28964 【元素组成】C 69.22% H 6.2% O 24.59% |
合成路线1
该中间体在本合成路线中的序号：(III)Condensation of 7-hydroxy-4,8-dimethylcoumarin (I) with 3-chloro-2-butanone (II) affords the keto alkoxycoumarin (III), which is cyclized to the psoralen derivative (IV) under basic conditions. Benzylic bromination of (IV) by means of N-bromosuccinimide provides the bromomethyl compound (V) as the major isomer. Bromide (V) is then condensed with N-(2-hydroxyethyl)phthalimide (VI) to furnish ether (VII). The phthaloyl group of (VII) is removed by treatment with either primary amines or with hydrazine to produce the target free amine, which is finally isolated as the corresponding hydrochloride salt.
| 【1】 Wollowitz, S.; Isaacs, S.T.; Rapoport, H.; Spielmann, H.P. (Steritech, Inc.); Cpds. for the photodecontamination of pathogens in blood. US 5399719; WO 9500141 . |
| 【2】 Wollowitz, S.; Isaacs, S.T.; Rapoport, H.; Spielman, H.P.; Niero, A. (Steritech, Inc.); Cpds. for the photodecontamination of pathogens in blood. WO 9614739 . |
| 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) | 58850 | 4,8-Dimethyl-7-hydroxycoumarin | C11H10O3 | 详情 | 详情 | |
| (II) | 12423 | 3-Chloro-2-butanone | 4091-39-8 | C4H7ClO | 详情 | 详情 |
| (III) | 58851 | 4,8-dimethyl-7-(1-methyl-2-oxopropoxy)-2H-chromen-2-one | C15H16O4 | 详情 | 详情 | |
| (IV) | 58852 | 2,3,5,9-tetramethyl-7H-furo[3,2-g]chromen-7-one | C15H14O3 | 详情 | 详情 | |
| (V) | 58853 | 3-(bromomethyl)-2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one | C15H13BrO3 | 详情 | 详情 | |
| (VI) | 58854 | 2-(2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione;N-Hydroxyethylphthalimide;N-(2-Hydroxyethyl)phthalimide;2-(2-hydroxyethyl)isoindoline-1,3-dione | 3891-07-4 | C10H9NO3 | 详情 | 详情 |
| (VII) | 58855 | 2-{2-[(2,5,9-trimethyl-7-oxo-7H-furo[3,2-g]chromen-3-yl)methoxy]ethyl}-1H-isoindole-1,3(2H)-dione | C25H21NO6 | 详情 | 详情 |