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【结 构 式】 
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【分子编号】47450 【品名】ethyl 3,3-bis(4-chlorophenyl)-2-oxiranecarboxylate 【CA登记号】 |
【 分 子 式 】C17H14Cl2O3 【 分 子 量 】337.20176 【元素组成】C 60.55% H 4.18% Cl 21.03% O 14.23% |
合成路线1
该中间体在本合成路线中的序号：(III)Darzen’s condensation of 4,4'-dichlorobenzophenone (I) with ethyl chloroacetate (II) produced the glycidic ester (III), which was subsequently converted to aldehyde (IV) upon treatment with KOH. Diol (V) was then obtained by Tollens’ reaction of aldehyde (IV) with formaldehyde. Ethyl 4-chlorophenylglyoxylate (VII) was prepared by addition of the Grignard reagent prepared from 1-bromo-4-chlorobenzene (VI) to diethyl oxalate. The condensation between diol (V) and keto ester (VII) in the presence of boron trifluoride furnished the cyclic ketal (VIII). Finally, saponification of the ethyl ester group gave rise to the target carboxylic acid.
| 【1】 Al Hazaa, A.; et al.; ZD1839 (Iressa(TM)), an EGFR-TKI, and cisplatin have an additive effect on programmed cell death in human head and neck squamous carcinoma cells in vitro. Clin Cancer Res 2000, 6, Suppl., Poster Nº 308. |
| 【2】 Zeiller, J.-J.; Raspé, E.; Guerrier, D.; Berthelon, J.-J. (Merck Patent GmbH); Cyclic cpds. useful in the treatment of dyslipidaemia, atherosclerosis and diabetes, pharmaceutical compsns. and preparation process. EP 1098893; FR 2781222; WO 0004011 . |
| 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) | 47449 | bis(4-chlorophenyl)methanone | 90-98-2 | C13H8Cl2O | 详情 | 详情 |
| (II) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (III) | 47450 | ethyl 3,3-bis(4-chlorophenyl)-2-oxiranecarboxylate | C17H14Cl2O3 | 详情 | 详情 | |
| (IV) | 47451 | 2,2-bis(4-chlorophenyl)acetaldehyde | C14H10Cl2O | 详情 | 详情 | |
| (V) | 47452 | 2,2-bis(4-chlorophenyl)-1,3-propanediol | C15H14Cl2O2 | 详情 | 详情 | |
| (VI) | 14733 | 4-Bromochlorobenzene; 1-bromo-4-chlorobenzene | 106-39-8 | C6H4BrCl | 详情 | 详情 |
| (VII) | 47453 | ethyl 2-(4-chlorophenyl)-2-oxoacetate | C10H9ClO3 | 详情 | 详情 | |
| (VIII) | 47454 | ethyl 2,5,5-tris(4-chlorophenyl)-1,3-dioxane-2-carboxylate | C25H21Cl3O4 | 详情 | 详情 |