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【结 构 式】

【分子编号】26082

【品名】(E)-2-methyl-7-phenyl-2-heptenoic acid

【CA登记号】

【 分 子 式 】C14H18O2

【 分 子 量 】218.29572

【元素组成】C 77.03% H 8.31% O 14.66%

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:(IV)

The reaction of 5-phenylpentanal (I) with triethyl 2-phosphonopropionate (II) by means of NaOEt in THF gives ethyl 2-methyl-7-phenyl-2(E)-heptenoate (III), which is hydrolyzed with NaOH in methanol/water to the corresponding free acid (IV). The reaction of (IV) with 4-methoxythiophenol (V) in hot piperidine affords 3-(4-methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (VI), which by reaction first with oxalyl chloride, then with O-trimethylsilylhydroxylamine (VII) in dichloromethane, and finally with HCl is converted into the hydroxamic acid (VIII). Finally, this compound is oxidized with oxone in methanol/water to provide the target compound as mixture of diastereomeric racemates that is separated by reversed phase HPLC.

1 Groneberg, R.D.; Neuenschwander, K.W.; Djuric, S.W.; McGeehan, G.M.; Burns, C.J.; Condon, S.M.; Morrissette, M.M.; Salvino, J.M.; Scotese, A.C.; Ullrich, J.W. (Aventis Pharma SA); Substd. (aryl, heteroaryl, arylmethyl or heteroarylmethyl) hydroxamic acid cpds.. EP 0871439; JP 2000503012; WO 9724117 .
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) 25636 5-phenylpentanal C11H14O 详情 详情
(II) 18816 ethyl 2-(diethoxyphosphoryl)propanoate 3699-66-9 C9H19O5P 详情 详情
(III) 26081 ethyl (E)-2-methyl-7-phenyl-2-heptenoate C16H22O2 详情 详情
(IV) 26082 (E)-2-methyl-7-phenyl-2-heptenoic acid C14H18O2 详情 详情
(V) 25639 4-methoxyphenylhydrosulfide; 4-methoxybenzenethiol 34320-82-6 C7H8OS 详情 详情
(VI) 26083 3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanoic acid C21H26O3S 详情 详情
(VII) 26091 O-(trimethylsilyl)hydroxylamine; (aminooxy)(trimethyl)silane 22737-36-6 C3H11NOSi 详情 详情
(VIII) 26084 N-hydroxy-3-[(4-methoxyphenyl)sulfanyl]-2-methyl-7-phenylheptanamide C21H27NO3S 详情 详情
Extended Information