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【结 构 式】 
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【分子编号】18587 【品名】2-(1-naphthyl)acetonitrile 【CA登记号】132-75-2 |
【 分 子 式 】C12H9N 【 分 子 量 】167.2102 【元素组成】C 86.2% H 5.43% N 8.38% |
合成路线1
该中间体在本合成路线中的序号：(I)Reduction of 1-naphthylacetonitrile (1) by catalytic hydrogenation using Raney Nickel in a NH3 saturated EtOH solution afforded 2-(1-naphthyl)ethylamine, which was then converted to hydrochloride salt (II). Further condensation with cyclobutanecarbonyl chloride (III) in the presence of K2CO3 provided the target amide.
| 【1】 Leclerc, V.; Fourmaintraux, E.; Depreux, P.; Lesieur, D.; Morgan, P.; Howell, H.E.; Renard, P.; Caignard, D.H.; Pfeiffer, B.; Delagrange, P.; Guardiola-Lemaitre, B.; Andrieux, J.; Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. Bioorg Med Chem 1998, 6, 10, 1875. |
合成路线2
该中间体在本合成路线中的序号：(I)The condensation of 2-(1-naphthyl)acetonitrile (I) with 2-bromobutyric acid ethyl ester (II) by means of K2CO3 gives 2-ethyl-4-(!-naphthyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) by means of NaOMe yielding 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is condensed with methylsulfanylmethyl iodide (VI) to afford the title pyrimidinone derivative.
| 【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
| 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) | 18587 | 2-(1-naphthyl)acetonitrile | 132-75-2 | C12H9N | 详情 | 详情 |
| (II) | 36668 | ethyl 2-bromobutanoate | 533-68-6 | C6H11BrO2 | 详情 | 详情 |
| (III) | 51802 | ethyl 2-ethyl-4-(1-naphthyl)-3-oxobutanoate | C18H20O3 | 详情 | 详情 | |
| (IV) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (V) | 51803 | 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C17H16N2OS | 详情 | 详情 | |
| (VI) | 51805 | iodomethyl methyl sulfide; iodo(methylsulfanyl)methane | C2H5IS | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The condensation of 2-(1-naphthyl)acetonitrile (I) with 2-bromobutyric acid ethyl ester (II) by means of K2CO3 gives 2-ethyl-4-(!-naphthyl)-3-oxobutyric acid ethyl ester (III), which is cyclized with thiourea (IV) by means of NaOMe yielding 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (V). Finally this compound is condensed with ethylsulfanylmethyl iodide (VI) to afford the title pyrimidinone derivative.
| 【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
| 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) | 18587 | 2-(1-naphthyl)acetonitrile | 132-75-2 | C12H9N | 详情 | 详情 |
| (II) | 36668 | ethyl 2-bromobutanoate | 533-68-6 | C6H11BrO2 | 详情 | 详情 |
| (III) | 51802 | ethyl 2-ethyl-4-(1-naphthyl)-3-oxobutanoate | C18H20O3 | 详情 | 详情 | |
| (IV) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (V) | 51803 | 5-ethyl-6-(1-naphthylmethyl)-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C17H16N2OS | 详情 | 详情 | |
| (VI) | 51804 | ethyl iodomethyl sulfide; 1-[(iodomethyl)sulfanyl]ethane | C3H7IS | 详情 | 详情 |