|
【结 构 式】 
|
【分子编号】26683 【品名】(4S,5R)-4-(1-methoxy-1-methylethoxy)-5-methyl-2-cyclopenten-1-one 【CA登记号】 |
【 分 子 式 】C10H16O3 【 分 子 量 】184.23524 【元素组成】C 65.19% H 8.75% O 26.05% |
合成路线1
该中间体在本合成路线中的序号：(II)The cyclization of the diacyl cyclopropane (I) with cyclopentenone (II) gives the tricyclic epoxide (III), which is converted into the unsaturated epoxydione (IV). Hydroxylation of the double bond of (IV) affords the diol (V), which is protected as cyclic ketal, with simultaneous ring opening of the epoxide and methylation of one ketonic group to give intermediate (VI). Elimination of the ketal group and simultaneous acetylation yields the monoacetoxytetrahydroindenone (VII), which is converted into the dihydroindenone (VIII). Finally, this compound is hydroxymethylated with paraformaldehyde.
| 【1】 McMorris, T.C.; Discovery and development of sesquiterpenoid derived hydroxymethylacylfulvene: A new anticancer drug. Bioorg Med Chem 1999, 7, 5, 881. |
| 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) | 26682 | 1-(1-Acetylcyclopropyl)-2-diazo-1-ethanone | C7H8N2O2 | 详情 | 详情 | |
| (II) | 26683 | (4S,5R)-4-(1-methoxy-1-methylethoxy)-5-methyl-2-cyclopenten-1-one | C10H16O3 | 详情 | 详情 | |
| (III) | 26684 | (2R,3S,3aS,4R,7S,7aS)-4,7-Epoxy-3-(1-methoxy-1-methylethoxy)-2,7-dimethylspiro[perhydroindane-6,1'-cyclopropane]-1,5-dione; (2R,3S,3aS,4R,7S,7aS)-4,7-Epoxy-3-(1-methoxy-1-methylethoxy)-2,7-dimethylspiro[perhydroindane-6,1'-cyclopropane]-1,5-dione | C17H24O5 | 详情 | 详情 | |
| (IV) | 26685 | (3aR,4R,7S,7aS)-4,7-Epoxy-2,7-dimethyl-3a,4,5,6,7,7a-hexahydro-1H-spiro[indene-6,1'-cyclopropane]-1,5-dione; (3aR,4R,7S,7aS)-4,7-Epoxy-2,7-dimethyl-3a,4,5,6,7,7a-hexahydro-1H-spiro[indene-6,1'-cyclopropane]-1,5-dione | C13H14O3 | 详情 | 详情 | |
| (V) | 26686 | (2R,3R,3aR,4R,7S,7aS)-4,7-Epoxy-2,3-dihydroxy-2,7-dimethylperhydrospiro[indene-6,1'-cyclopropane]-15-dione | C13H16O5 | 详情 | 详情 | |
| (VI) | 26687 | (3aR,5R,8aR)-4,5-Dihydroxy-2-methoxy-5,7,8a-trimethyl-3b,4,5,6,8,8a-hexahydro-3aH-spiro[indeno[1,2-d][1,3]dioxole-6,1'-cyclopropan]-8-one | C16H22O6 | 详情 | 详情 | |
| (VII) | 26688 | (3aR,5R)-4-Acetoxy-5-hydroxy-2,5,7-trimethyl-3a,4,5,6-tetrahydro-1H-spiro[indene-6,1'-cyclopropan]-1-one | C16H20O4 | 详情 | 详情 | |
| (VIII) | 26689 | 6(R)-6-Hydroxy-2,4,6-trimethyl-6,7-dihydro-5H-spiro[indene-5,1'-cyclopropan]-7-one; 6(R)-6-Hydroxy-2,4,6-trimethyl-6,7-dihydro-5H-spiro[indene-5,1'-cyclopropan]-7-one | C14H16O2 | 详情 | 详情 |