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【结 构 式】

【分子编号】56670

【品名】cis-10-Heptadecenoic acid

【CA登记号】29743-97-3

【 分 子 式 】C17H32O2

【 分 子 量 】268.43988

【元素组成】C 76.06% H 12.02% O 11.92%

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:(I)

Irisquinone was originally isolated from some Iris species. The total synthesis of this compound has been reported by several procedures. 10-cis-Heptadecenoic acid (I) was converted to the Weinreb amide (II) via the corresponding acid chloride. Regiospecific ortho-lithiation of veratrole (III), followed by acylation with the N-methoxy amide (II), afforded ketone (IV). Selective mono-demethylation of (IV) with boron trichloride yielded phenol (V). Clemmensen reduction of the keto group of (V) employing zinc amalgam furnished 2-(cis-10-heptadecenyl)-6-methoxyphenol (VI). This was finally oxidized to the target quinone by means of oxygen gas in the presence of salcomine.

1 Haugwitz, R.D.; Risbood, P.A.; Parsons, J.L.; Myers, D.R.; Michalak, R.S.; Narayanan, V.L.; The synthesis of irisquinone. Tetrahedron Lett 1989, 30, 36, 4783.
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) 56670 cis-10-Heptadecenoic acid 29743-97-3 C17H32O2 详情 详情
(II) 56671 (Z)-N-methoxy-N-methyl-10-heptadecenamide C19H37NO2 详情 详情
(III) 17395 1-(4-fluorophenethyl)-4-piperidinecarboxamide C14H19FN2O 详情 详情
(IV) 56672 (Z)-1-(2,3-dimethoxyphenyl)-10-heptadecen-1-one C25H40O3 详情 详情
(V) 56673 (Z)-1-(2-hydroxy-3-methoxyphenyl)-10-heptadecen-1-one C24H38O3 详情 详情
(VI) 56674 2-[(Z)-10-heptadecenyl]-6-methoxyphenol C24H40O2 详情 详情
Extended Information