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【结 构 式】 
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【分子编号】34529 【品名】ethyl 2-[3-(3-methoxyphenyl)-1H-inden-1-yl]acetate 【CA登记号】 |
【 分 子 式 】C20H20O3 【 分 子 量 】308.377 【元素组成】C 77.9% H 6.54% O 15.56% |
合成路线1
该中间体在本合成路线中的序号：(XVII)The synthesis of the tricyclic precursors has been reported by two alternative routes. Alkylation of 3-(3-methoxyphenyl)indene (XVI) with ethyl bromoacetate using lithium hexamethyldisilazide provided indeneacetate (XVII). Subsequent oxidative cleavage of (XVII) gave rise to the arylsuccinic derivative (XVIII). The benzoyl group of (XVIII) was then reduced to the benzyl analogue (XIX) by catalytic hydrogenation in the presence of Pd/C in AcOH. After conversion of (XIX) to the corresponding acid chloride (XX), Friedel-Crafts cyclization produced the tricyclic ketoester (XXI). Then reduction of the ketone group of (XXI) by hydrogenation over Pd/C furnished intermediate (IX).
| 【1】 Miller, W.H.; Samanen, J.M.; Heerding, D.; Bondinell, W.E. (SmithKline Beecham Corp.); Vitronectin receptor antagonists. EP 1025090; WO 9915508 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 | |
| (IX) | 34522 | ethyl 2-(3-methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)acetate | C20H22O3 | 详情 | 详情 | |
| (XVI) | 34528 | 3-(3-methoxyphenyl)-1H-indene; 3-(1H-inden-3-yl)phenyl methyl ether | C16H14O | 详情 | 详情 | |
| (XVII) | 34529 | ethyl 2-[3-(3-methoxyphenyl)-1H-inden-1-yl]acetate | C20H20O3 | 详情 | 详情 | |
| (XVIII) | 34530 | 4-ethoxy-2-[2-(3-methoxybenzoyl)phenyl]-4-oxobutyric acid | C20H20O6 | 详情 | 详情 | |
| (XIX) | 34531 | 4-ethoxy-2-[2-(3-methoxybenzyl)phenyl]-4-oxobutyric acid | C20H22O5 | 详情 | 详情 | |
| (XX) | 34532 | ethyl 4-chloro-3-[2-(3-methoxybenzyl)phenyl]-4-oxobutanoate | C20H21ClO4 | 详情 | 详情 | |
| (XXI) | 34533 | ethyl 2-(3-methoxy-11-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)acetate | C20H20O4 | 详情 | 详情 |