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【结 构 式】 
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【分子编号】20001 【品名】(3Z)-4-(4-chlorophenyl)-4-hydroxy-2,3-dimethoxy-1,3-butadien-1-one 【CA登记号】 |
【 分 子 式 】C12H11ClO4 【 分 子 量 】254.66964 【元素组成】C 56.6% H 4.35% Cl 13.92% O 25.13% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(V)The metalation of 4-chlorobromobenzene (I) with lithium gives 4-chlorophenyllithium (II), which is condensed with dimethyl squarate (III) in THF at -78 C giving 4-(4-chlorophenyl)-4-hydroxy-2,3-dimethoxy-2-cyclobuten-1-one (IV). The isomerization of (IV) in refluxing xylene (38 C) affords naphthohydroquinone (VI) through the intermediate ketene (V). Finally, compound (VI) is acetylated with acetic anhydride in pyridine - dimethylaminopyridine.
| 【1】 Perri, S.T.; Moore, H.W.; Synthesis of lonapalene. Tetrahedron Lett 1987, 28, 39, 4507-10. |
| 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) | 14733 | 4-Bromochlorobenzene; 1-bromo-4-chlorobenzene | 106-39-8 | C6H4BrCl | 详情 | 详情 |
| (II) | 19396 | (4-chlorophenyl)lithium | C6H4ClLi | 详情 | 详情 | |
| (III) | 19999 | 3,4-dimethoxy-3-cyclobutene-1,2-dione | 5222-73-1 | C6H6O4 | 详情 | 详情 |
| (IV) | 20000 | 4-(4-chlorophenyl)-4-hydroxy-2,3-dimethoxy-2-cyclobuten-1-one | C12H11ClO4 | 详情 | 详情 | |
| (V) | 20001 | (3Z)-4-(4-chlorophenyl)-4-hydroxy-2,3-dimethoxy-1,3-butadien-1-one | C12H11ClO4 | 详情 | 详情 | |
| (VI) | 20002 | 6-chloro-2,3-dimethoxy-1,4-naphthalenediol | C12H11ClO4 | 详情 | 详情 |
Extended Information