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【结 构 式】 
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【分子编号】27345 【品名】5-methyl-2,4-dihydro-3H-pyrazol-3-one 【CA登记号】108-26-9 |
【 分 子 式 】C4H6N2O 【 分 子 量 】98.10452 【元素组成】C 48.97% H 6.16% N 28.55% O 16.31% |
合成路线1
该中间体在本合成路线中的序号：(IV)Compound can be prepared in three different ways: 1) By cyclization of 2-(2-naphthyloxy)ethylhydrazine (I) with ethyl acetoacetate (II) in refluxing ethanol. 2) By cyclization of 2-(2-naphthyloxy)ethylhydrazine (I) with tetrolic acid ethyl ester (III) in refluxing n-butanol. 3) By condensation of 3-methylpyrazol-5-one (IV) with 2-(2-naphthyloxy)ethyl bromide (V) by means of NaH in DMF or by heating at 110 C.
| 【1】 Moeller, E.; et al.; US 4113957 . |
| 【2】 Prous, J.R.; Hillier, K.; BAY-g-6575. Drugs Fut 1979, 4, 6, 396. |
| 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) | 39494 | 1-[2-(2-naphthyloxy)ethyl]hydrazine; 2-hydrazinoethyl 2-naphthyl ether | C12H14N2O | 详情 | 详情 | |
| (II) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (III) | 39495 | ethyl 2-butynoate | 4341-76-8 | C6H8O2 | 详情 | 详情 |
| (IV) | 27345 | 5-methyl-2,4-dihydro-3H-pyrazol-3-one | 108-26-9 | C4H6N2O | 详情 | 详情 |
| (V) | 39496 | 2-(2-bromoethoxy)naphthalene; 2-bromoethyl 2-naphthyl ether | C12H11BrO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Suspension of 3-methyl-2-pyrazolin-5-one (I) is added dropwise under stirring to ethyl acetoacetate (II), which has been heated to 140 C, water and ethanol formed in the reaction are distilled off, and the mixture is heated at reflux. Upon completion of the reaction, the mixture is allowed to stand at room temperature, and the solid thus separated is collected and recrystallized from ethanol to obtain the title compound.
| 【1】 J Taiwan Pharm Assoc 1979, 31, 47-55. |
| 【2】 Kuo, S.C.; et al.; Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives. J Med Chem 1984, 27, 4, 539. |
| 【3】 Teng, C.M.; Kuo, S.C.; Wang, J.P.; XC-386. Drugs Fut 1985, 10, 9, 761. |