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Dicyclohexylcarbodiimide → 2-[1-(trans-2-Pentenoyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthoquinone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | 2-Pentenoic acid | HCID 12299 | — |
| 反応物 | Shikonin | HCID 479503 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 2-[1-(trans-2-Pentenoyloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthoquinone | HCID 21468087 | 25.6% |
反応手順
288 mg (1 mmole) of shikonin, 226 mg (1.1 mmole) of dicyclohexylcarbodiimide and 30 mg (0.25 mmole) of 4-dimethylaminopyridine were dissolved in 3 ml of dry dichloromethane. To the resulting solution was added 100 mg (1 mmole) of n-pentenoic acid at 0° C. under nitrogen gas, and the mixture was stirred for 30 minutes and then at room temperature for further 3 hours. The resulting product was separated and purified according to the procedures as described in Example 1 to obtain 95 mg (Yield: 23%) of the title compound having the following structure as a red precipitate.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05696276 |
| 出典データセット | uspto-grants-1997_12 |
| ORD ID | ord-111412bffa634e928014f332c5823b1e |
| 出典メモ | uspto-grants-1997_12 |