【结 构 式】 |
【分子编号】25640 【品名】tert-butyl 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoate 【CA登记号】 |
【 分 子 式 】C24H32O3S 【 分 子 量 】400.58228 【元素组成】C 71.96% H 8.05% O 11.98% S 8% |
合成路线1
该中间体在本合成路线中的序号:(V)Horner-Emmons condensation of 5-phenylpentanal (I) with phosphonate (II) in the presence of NaH yielded tert-butyl 7-phenyl-2-heptenoate (III). Subsequent Michael addition of 4-methoxythiophenol (IV) to (III) using a catalytic amount of BuLi provided thioether (V). After acid deprotection of the tert-butyl ester of (V) with TFA, the resulting carboxylic acid (VI) was converted to acid chloride (VII) and then condensed with O-(trimethylsilyl)hydroxylamine to produce hydroxamic acid (VIII). Finally, sulfide oxidation of (VIII) with Oxone furnished the target beta-sulfonylhydroxamic acid. Alternatively tet-butyl ester (III) can be hydrolyzed first to the free acid (IX) with TFA, and then condensed with thiophenol (IV) by means of piperidine to afford the previously described carboxylic acid (VI).
【1】 Burns, C.J.; Groneberg, R.D.; Morrissette, M.M.; et al.; Dual inhibition of phosphodiesterase 4 and matrix metalloproteinases by an (arylsulfonyl)hydroxamic acid template. J Med Chem 1999, 42, 4, 541. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
26091 | O-(trimethylsilyl)hydroxylamine; (aminooxy)(trimethyl)silane | 22737-36-6 | C3H11NOSi | 详情 | 详情 | |
(I) | 25636 | 5-phenylpentanal | C11H14O | 详情 | 详情 | |
(II) | 25637 | tert-butyl 2-(diethoxyphosphoryl)acetate | 6273-47-8 | C10H21O5P | 详情 | 详情 |
(III) | 25638 | tert-butyl (E)-7-phenyl-2-heptenoate | C17H24O2 | 详情 | 详情 | |
(IV) | 25639 | 4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol | 34320-82-6 | C7H8OS | 详情 | 详情 |
(V) | 25640 | tert-butyl 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoate | C24H32O3S | 详情 | 详情 | |
(VI) | 25641 | 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoic acid | C20H24O3S | 详情 | 详情 | |
(VII) | 25642 | 3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanoyl chloride | C20H23ClO2S | 详情 | 详情 | |
(VIII) | 25643 | N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-7-phenylheptanamide | C20H25NO3S | 详情 | 详情 | |
(IX) | 25644 | (E)-7-phenyl-2-heptenoic acid | C13H16O2 | 详情 | 详情 |