化工社化工社 化学情報印刷レポート · 研究参考用
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Isoflavone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| 反応物 | Chroman-4-ol | HCID 92890 | — |
| 反応物 | 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran | HCID 59592104 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Isoflavone | HCID 72304 | — |
反応手順
Using the general procedure of hydroboration-oxidation, compound 1 was converted into a chroman-4-ol (compound 4) at a yield of 60%. Compound 4 was treated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing 1,4-dioxane to undergo oxidation-dehydrogenation to give an isoflavone (compound 5) at a yield of 78%. After the deprotection of compound 5 with AlCl3/EtSH, daidzein (compound 6a) was produced at a yield of 92%. On the other hand, compound 5 could be selectively debenzylated with Pearlman's reagent to give formononetin (compound 6b) at a yield of 94%,
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07875735B2 |
| 出典データセット | uspto-grants-2011_01 |
| ORD ID | ord-5045789148ff4eb897b535c7708cd250 |
| 出典メモ | uspto-grants-2011_01 |