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【结 构 式】 
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【分子编号】20570 【品名】2-(1-propynyl)-1,3,2lambda(5)-dioxaphosphinan-2-one 【CA登记号】 |
【 分 子 式 】C6H9O3P 【 分 子 量 】160.109422 【元素组成】C 45.01% H 5.67% O 29.98% P 19.35% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of trimethylene glycol (I) with PCl3 gives 2-chloro-1,3,2-dioxaphosphorinane (II), which is condensed with propargyl alcohol (III) by means of triethylamine in acetonitrile to give a mixture of 2-allenyl- and 2-propargyl-2-oxo-1,3,2-dioxaphosphorinane (IV and V). The reaction of this mixture with isobutylamine in acetonitrile affords 2-(2-isobutylamino-1-propenyl)-2-oxo-1,3,2-dioxaphosphorinane (VI). The hydrolysis of the enamine (VI) with malonic acid gives 2-acetonyl-2-oxo-1,3,2-dioxaphosphorinane (VII), which is condensed with isobutyl-(2-nitrobenzylidene)amine (VIII) to yield 2-[1-(2-nitrobenzylidene)-2-oxopropyl]-2-oxo-1,3,2-dioxaphosphorinane (IX). Finally, this compound is cyclized with methyl 3-aminocrotonate (X) in refluxing acetonitrile.
| 【1】 Morita, I.; Tsuda, M.; Kise, M.; Sugiyama, M.; Improved synthesis of methyl 2, 6-dimethyl-4-(2-nitrophenyl)-5-(2-oxo-1,3, 2-dioxaphosphorinan-2-yl)-1, 4-dihydropyridine-3-carboxylate (DHP-218). Chem Pharm Bull 1988, 36, 3, 1139-42. |
| 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) | 14685 | 1,3-propanediol; Trimethylene Glycol | 504-63-2 | C3H8O2 | 详情 | 详情 |
| (II) | 20567 | 2-chloro-1,3,2-dioxaphosphinane | C3H6ClO2P | 详情 | 详情 | |
| (III) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
| (IV) | 20569 | 2-(1,2-propadienyl)-1,3,2lambda(5)-dioxaphosphinan-2-one | C6H9O3P | 详情 | 详情 | |
| (V) | 20570 | 2-(1-propynyl)-1,3,2lambda(5)-dioxaphosphinan-2-one | C6H9O3P | 详情 | 详情 | |
| (VI) | 20571 | 2-[(E)-2-(isobutylamino)-1-propenyl]-1,3,2lambda(5)-dioxaphosphinan-2-one | C10H20NO3P | 详情 | 详情 | |
| (VII) | 20572 | 2-(2-oxopropyl)-1,3,2lambda(5)-dioxaphosphinan-2-one | C6H11O4P | 详情 | 详情 | |
| (VIII) | 20573 | 2-methyl-N-[(Z)-(2-nitrophenyl)methylidene]-1-propanamine; N-isobutyl-N-[(Z)-(2-nitrophenyl)methylidene]amine | C11H14N2O2 | 详情 | 详情 | |
| (IX) | 20574 | 2-[(Z)-1-acetyl-2-(2-nitrophenyl)ethenyl]-1,3,2lambda(5)-dioxaphosphinan-2-one | C13H14NO6P | 详情 | 详情 | |
| (X) | 11372 | Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate | C5H9NO2 | 详情 | 详情 | |
| (XI) | 12963 | Malonic acid | 141-82-2 | C3H4O4 | 详情 | 详情 |