【结 构 式】 |
【分子编号】23173 【品名】4-[(4-methoxyphenyl)sulfinyl]benzaldehyde 【CA登记号】 |
【 分 子 式 】C14H12O3S 【 分 子 量 】260.31348 【元素组成】C 64.6% H 4.65% O 18.44% S 12.32% |
合成路线1
该中间体在本合成路线中的序号:(VII)Oxidation of disulfide (I) with sulfuryl chloride in AcOH at -20 C afforded (4-methoxyphenyl)sulfinyl chloride (II), which was condensed with (1R,2S)-2-phenylcyclohexanol to provide sulfinate (IV) as a single diastereomer. Subsequent condensation with the Grignard reagent (V) produced the chiral sulfoxide (VI). The diethyl acetal of (VI) was then hydrolyzed to the corresponding benzaldehyde (VII) using p-TsOH in THF-H2O. Finally, condensation of (VII) with N-cyclohexylpiperazine (VIII) using titanium tetraisopropoxide, followed by addition of diethylaluminum cyanide, furnished the target piperazinylacetonitrile.
【1】 Lowe, D.B.; Guzik, H.S.; Kozlowski, J.A.; et al.; Diphenyl sulfoxides as selective antagonists of the muscarinic M2 receptor. Bioorg Med Chem Lett 2000, 10, 20, 2255. |
【2】 Lowe, D.; Chang, W.; Kozlowski, J.; Berger, J.G.; McQuade, R.; Barnett, A.; Scherlock, M.; Tom, W.; Dugar, S.; Chen, L.-Y.; Clader, J.W.; Chackalamannil, S. (Schering Corp.); Benzylpiperidines and piperazines as muscarinic an. EP 0811002; JP 1999501014; US 5883096; WO 9626196 . |
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) | 23167 | 1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene; bis(4-methoxyphenyl) disulfide | 5335-87-5 | C14H14O2S2 | 详情 | 详情 |
(II) | 23168 | 4-methoxybenzenesulfinyl chloride | C7H7ClO2S | 详情 | 详情 | |
(III) | 23169 | (1S,2R)-2-phenylcyclohexanol | C12H16O | 详情 | 详情 | |
(IV) | 23170 | (1S,2R)-2-phenylcyclohexyl 4-methoxybenzenesulfinate | C19H22O3S | 详情 | 详情 | |
(V) | 23171 | bromo[4-(diethoxymethyl)phenyl]magnesium | C11H15BrMgO2 | 详情 | 详情 | |
(VI) | 23172 | [4-(diethoxymethyl)phenyl](4-methoxyphenyl)oxo-lambda(4)-sulfane; 4-(diethoxymethyl)phenyl 4-methoxyphenyl sulfoxide | C18H22O4S | 详情 | 详情 | |
(VII) | 23173 | 4-[(4-methoxyphenyl)sulfinyl]benzaldehyde | C14H12O3S | 详情 | 详情 | |
(VIII) | 23174 | 1-cyclohexylpiperazine | 17766-28-8 | C10H20N2 | 详情 | 详情 |