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【结 构 式】 
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【分子编号】56690 【品名】3-[(Z)-10-heptadecenyl]-2,5-bis(methoxymethoxy)phenyl methyl ether; 1-[(Z)-10-heptadecenyl]-3-methoxy-2,5-bis(methoxymethoxy)benzene 【CA登记号】 |
【 分 子 式 】C28H48O5 【 分 子 量 】464.68612 【元素组成】C 72.37% H 10.41% O 17.22% |
合成路线1
该中间体在本合成路线中的序号：(XXIII)Alternatively, the bis-methoxymethyl ether (XVIII), prepared from 2-bromo-6-methoxyhydroquinone (XVII), was subjected to palladium-catalyzed coupling with 9-decen-1-ol (XIX) to afford adduct (XX). After catalytic hydrogenation of olefin (XX), the resultant saturated alcohol (XXI) was oxidized to aldehyde (XXII) under Swern conditions. Wittig condensation of (XXII) with the phosphonium salt (XV) led to the heptadecenyl derivative (XXIII). Subsequent hydrolysis of the methoxymethyl ethers of (XXIII) by means of HBr in EtOH furnished the deprotected hydroquinone (XXIV). This was finally oxidized to the title quinone employing silver carbonate in benzene.
| 【1】 Yadav, J.S.; et al.; A practical preparation of functionalized alkylbenzoquinones synthesis of maesanin and irisquinone. J Org Chem 1992, 57, 11, 3242. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 56682 | heptyl(triphenyl)phosphonium bromide | 13423-48-8 | C25H30BrP | 详情 | 详情 |
| (XVII) | 56684 | 2-bromo-6-methoxy-1,4-benzenediol | C7H7BrO3 | 详情 | 详情 | |
| (XVIII) | 56685 | 1-bromo-3-methoxy-2,5-bis(methoxymethoxy)benzene; 3-bromo-2,5-bis(methoxymethoxy)phenyl methyl ether | C11H15BrO5 | 详情 | 详情 | |
| (XIX) | 56686 | 9-Decen-1-ol; 9-Decene-1-ol; omega-Decen-1-ol; Trepanol; Decylenic alcohol | 13019-22-2 | C10H20O | 详情 | 详情 |
| (XX) | 56687 | (E)-10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]-9-decen-1-ol | C21H34O6 | 详情 | 详情 | |
| (XXI) | 56688 | 10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]-1-decanol | C21H36O6 | 详情 | 详情 | |
| (XXII) | 56689 | 10-[3-methoxy-2,5-bis(methoxymethoxy)phenyl]decanal | C21H34O6 | 详情 | 详情 | |
| (XXIII) | 56690 | 3-[(Z)-10-heptadecenyl]-2,5-bis(methoxymethoxy)phenyl methyl ether; 1-[(Z)-10-heptadecenyl]-3-methoxy-2,5-bis(methoxymethoxy)benzene | C28H48O5 | 详情 | 详情 | |
| (XXIV) | 56691 | 2-[(Z)-10-heptadecenyl]-6-methoxy-1,4-benzenediol | C24H40O3 | 详情 | 详情 |