Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Isoflavone
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| 반응물 | Chroman-4-ol | HCID 92890 | — |
| 반응물 | 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran | HCID 59592104 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | Isoflavone | HCID 72304 | — |
반응 단계
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%,
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07875735B2 |
| 출처 데이터셋 | uspto-grants-2011_01 |
| ORD ID | ord-5045789148ff4eb897b535c7708cd250 |
| 출처 메모 | uspto-grants-2011_01 |