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【结 构 式】 
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【分子编号】10967 【品名】trans-3-Benzyloxy-4-methoxy-beta-nitrostyrene; Benzyl 2-methoxy-5-[(E)-2-nitroethenyl]phenyl ether; 2-(Benzyloxy)-1-methoxy-4-[(E)-2-nitroethenyl]benzene 【CA登记号】63909-29-5 |
【 分 子 式 】C16H15NO4 【 分 子 量 】285.29944 【元素组成】C 67.36% H 5.3% N 4.91% O 22.43% |
合成路线1
该中间体在本合成路线中的序号：(II)The enantioselective synthesis of the (R)-enantiomer of rolipram, which is the most active, has been published: The reaction of 3-benzyloxy-4-methoxybenzaldehyde (I) with nitromethane by means of ammonium acetate in refluxing acetic acid gives 3-benzyloxy-4-methoxy-beta-nitrostyrene (II), which is condensed with the chiral oxazolidinone (R)-3-acetyl-4-benzyl-2-oxazolidinone (III) by means of sodium bis(trimethylsilyl)amine in THF yielding 4(R)-benzyl-3-[3(R)-(3-benzyloxy-4-methoxyphenyl)-4-nitrobutyryl]-2-oxa zolidinone (IV). Hydrogenation of (IV) with H2 over Raney Ni in ethanol - ethyl acetate affords 4(R)-(3-hydroxy-4-methoxyphenyl)-2-pyrrolidinone (VI) through the intermediate benzyl ether (V). Finally, compound (VI) is etherified with cyclopentyl bromide (VII) by means of NaH in refluxing THF.
| 【1】 Schmiechen, R.; Mulzer, J.; Zuhse, R.; Enantioselective synthesis of the antidepressant rolipram by Michael addition to a nitroolefin. Angew Chem. Int Ed Engl 1992, 31, 7, 870. |
| 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) | 10966 | 3-(Benzyloxy)-4-methoxybenzaldehyde; 3-Benzyloxy-4-methoxybenzaldehyde | 6346-05-0 | C15H14O3 | 详情 | 详情 |
| (II) | 10967 | trans-3-Benzyloxy-4-methoxy-beta-nitrostyrene; Benzyl 2-methoxy-5-[(E)-2-nitroethenyl]phenyl ether; 2-(Benzyloxy)-1-methoxy-4-[(E)-2-nitroethenyl]benzene | 63909-29-5 | C16H15NO4 | 详情 | 详情 |
| (III) | 10968 | (4R)-3-Acetyl-4-benzyl-1,3-oxazolidin-2-one; (R)-(-)-3-Acetyl-4-benzyl-2-oxazolidinone | 184363-65-3 | C12H13NO3 | 详情 | 详情 |
| (IV) | 10969 | (4R)-4-Benzyl-3-[(3S)-3-[3-(benzyloxy)-4-methoxyphenyl]-4-nitrobutanoyl]-1,3-oxazolidin-2-one | C28H28N2O7 | 详情 | 详情 | |
| (V) | 10970 | (4R)-4-[3-(Benzyloxy)-4-methoxyphenyl]-2-pyrrolidinone | C18H19NO3 | 详情 | 详情 | |
| (VI) | 10971 | (4R)-4-(3-Hydroxy-4-methoxyphenyl)tetrahydro-2H-pyrrol-2-one | C11H13NO3 | 详情 | 详情 | |
| (VII) | 10972 | 1-Bromocyclopentane; Cyclopentyl bromide | 137-43-9 | C5H9Br | 详情 | 详情 |