|
【结 构 式】 
|
【分子编号】63526 【品名】N-[2-(7-hydroxy-1-naphthalenyl)ethyl]acetamide 【CA登记号】 |
【 分 子 式 】C14H15NO2 【 分 子 量 】229.27864 【元素组成】C 73.34% H 6.59% N 6.11% O 13.96% |
合成路线1
该中间体在本合成路线中的序号：(II)Demethylation of N-[2-(7-methoxynaphth-1-yl)ethyl]acetamide (I) with boron tribromide-dimethyl sulfide complex affords phenol (II). This is then alkylated with 3-bromopropanol (III) in the presence of K2CO3 to provide the hydroxypropyl derivative (IV). After conversion of alcohol (IV) into the corresponding mesylate (V), condensation with a further equivalent of phenol (II) in hot DMF furnishes the target dimeric compound
| 【1】 Guillaumet, G.; Renard, P.; Lesieur, D.; Yous, S.; Descamps-Francois, C.; Lefoulon, F.; Viaud, M.-C.; Delagrange, P.; Bennejean, C. (ADIR et Cie.); Substd. dimeric cpds., process for their preparation and pharmaceutical compsns. thereof. EP 1038863; FR 2791344; JP 2000319242; US 2002035114; US 6319930; US 6635650 . |
| 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) | 63525 | N-{2-[7-(methyloxy)-1-naphthalenyl]ethyl}acetamide | C15H17NO2 | 详情 | 详情 | |
| (II) | 63526 | N-[2-(7-hydroxy-1-naphthalenyl)ethyl]acetamide | C14H15NO2 | 详情 | 详情 | |
| (III) | 12573 | 3-Bromo-1-propanol; 3-Bromopropanol | 627-18-9 | C3H7BrO | 详情 | 详情 |
| (IV) | 63527 | N-(2-{7-[(3-hydroxypropyl)oxy]-1-naphthalenyl}ethyl)acetamide | C17H21NO3 | 详情 | 详情 | |
| (V) | 63528 | 3-({8-[2-(acetylamino)ethyl]-2-naphthalenyl}oxy)propyl methanesulfonate | C18H23NO5S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)In an alternative method, the title dimer compound is obtained by condensation of two equivalents of N-[2-(7-hydroxynaphth-1-yl)ethyl]acetamide (I) with 1,3-dibromopropane (II) in the presence of K2CO3 in acetonitrile
| 【1】 Descamps-François, C.; Yous, S.; Chavatte, P.; Audinot, V.; Bonnaud, A.; Boutin, J.A.; Delagrange, P.; Bennejean, C.; Renard, P.; Lesieur, D.; Design and synthesis of naphthalenic dimers as selective MT1 melatoninergic ligands. J Med Chem 2003, 46, 7, 1127. |