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【结 构 式】 
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【分子编号】18087 【品名】N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-N-(2-chloroethyl)-N-methylamine; N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-2-chloro-N-methyl-1-ethanamine 【CA登记号】 |
【 分 子 式 】C24H32ClNO2 【 分 子 量 】401.97632 【元素组成】C 71.71% H 8.02% Cl 8.82% N 3.48% O 7.96% |
合成路线1
该中间体在本合成路线中的序号：(V)Treatment of chromane (I) with metanesulfonyl chloride in pyridine at 0 C afforded mesylate (II), which was treated with 2-methylaminoethanol (III) to afford tertiary amine (IV). Reaction with SOCl2 gave chloride (V), and further reaction with p-hydroxybenzaldehyde (VI) provided (VII). Aldehyde (VII) was then condensed with 2,4-thiazolidinedione (VIII) in the presence of piperidine benzoate in toluene to furnish (IX). Finally, the benzyl protecting group was removed by treatment with acetic acid-hydrochloric acid at 60 C to give the title compound.
| 【1】 Reddy, K.A.; Lohray, B.B.; Bhushan, V.; Reddy, A.S.; Kishore, P.H.; Rao, VV.; Saibaba, V.; Bajji, A.C.; Rajesh, B.M.; Reddy, K.V.; Chakrabarti, R.; Rajagopalan, R.; Novel euglycemic and hypolipidemic agents: Part-2. Antioxidant moiety as structural motif. Bioorg Med Chem Lett 1998, 8, 9, 999-1002. |
| 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) | 18084 | [6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methanol | C21H26O3 | 详情 | 详情 | |
| (II) | 18085 | [6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl methanesulfonate | C22H28O5S | 详情 | 详情 | |
| (III) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (IV) | 18086 | 2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]-1-ethanol | C24H33NO3 | 详情 | 详情 | |
| (V) | 18087 | N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-N-(2-chloroethyl)-N-methylamine; N-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]-2-chloro-N-methyl-1-ethanamine | C24H32ClNO2 | 详情 | 详情 | |
| (VI) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (VII) | 18088 | 4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]benzaldehyde | C31H37NO4 | 详情 | 详情 | |
| (VIII) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (IX) | 18089 | 5-[(Z)-(4-[2-[[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl](methyl)amino]ethoxy]phenyl)methylidene]-1,3-thiazolidine-2,4-dione | C34H38N2O5S | 详情 | 详情 |