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【结 构 式】 
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【分子编号】44043 【品名】4-(2-quinolinylmethoxy)phenyl benzoate 【CA登记号】 |
【 分 子 式 】C23H17NO3 【 分 子 量 】355.39292 【元素组成】C 77.73% H 4.82% N 3.94% O 13.51% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 2-(chloromethyl)quinoline (I) with hydroquinone monobenzoate (II) by means of K2CO3 in refluxing acetone/DMF gives 4-(2-quinolylmethoxy)phenyl benzoate (III), which is treated with sodium ethoxide in ethanol to yield 4-(2-quinolylmethoxy)phenol (IV). The condensation of (IV) with alpha,alpha'-dichloro-o-xylene (V) by means of NaH in THF affords the benzyl chloride derivative (VI), which is treated with NaCN in toluene/water with a phase-transfer catalyst to provide the benzyl cyanide derivative (VII). Finally, this compound is cyclized with sodium azide in hot DMF to afford the target tetrazole derivative.
| 【1】 Huang, F.-C.; (2-Quinolinylmethoxy)phenyl-containing compounds as leukotriene receptor antagonists: A brief review of structure-activity relationships and the biological profile of RG 12525. Drugs Fut 1991, 16, 12, 1121. |
| 【2】 Huang, F.-C.; et al.; Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene D4 receptor antagonists. 2. Effects of an additional phenyl ring on receptor affinity. J Med Chem 1990, 33, 4, 1194. |
| 【3】 Youssefyeh, R.D.; et al.; Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene receptor antagonists. 1. Initial structure-activity relationships. J Med Chem 1990, 33, 4, 1186. |
| 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) | 13162 | 2-(Chloromethyl)quinoline; alpha-Chloroquinaldine | 4377-41-7 | C10H8ClN | 详情 | 详情 |
| (II) | 44042 | 4-hydroxyphenyl benzoate | C13H10O3 | 详情 | 详情 | |
| (III) | 44043 | 4-(2-quinolinylmethoxy)phenyl benzoate | C23H17NO3 | 详情 | 详情 | |
| (IV) | 13164 | 4-(2-Quinolinylmethoxy)phenol | C16H13NO2 | 详情 | 详情 | |
| (V) | 13165 | 1,2-Bis(chloromethyl)benzene | 612-12-4 | C8H8Cl2 | 详情 | 详情 |
| (VI) | 13166 | 2-(Chloromethyl)benzyl 4-(2-quinolinylmethoxy)phenyl ether; 2-[(4-[[2-(Chloromethyl)benzyl]oxy]phenoxy)methyl]quinoline | C24H20ClNO2 | 详情 | 详情 | |
| (VII) | 13167 | 2-(2-[[4-(2-Quinolinylmethoxy)phenoxy]methyl]phenyl)acetonitrile | C25H20N2O2 | 详情 | 详情 |