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【结 构 式】

【分子编号】37655

【品名】1-isopropyl-2-(methoxymethoxy)-3-methylbenzene; (2-isopropyl-6-methylphenoxy)methyl methyl ether

【CA登记号】

【 分 子 式 】C12H18O2

【 分 子 量 】194.27372

【元素组成】C 74.19% H 9.34% O 16.47%

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:(III)

An enantioselective total synthesis of chloride (MOM-Cl) and NaH in THF gives the methoxymethyl ether (II), which is methylated with n-BuLi and methyl iodide in THF yielding the 6-methyl derivative (III). The condensation of (III) with 3-methyl-2-butenyl bromide (IV) by means of s-BuLi in THF affords compound (V), which is deprotected with LiBF4 and TMSCl in acetonitrile to give the phenol (VI). Methylation of (VI) with dimethyl sulfate and K2CO3 in refluxing acetone provides the ether (VII), which is hydroxylated at the terminal methyl group with SeO2 and tert-butyl hydroperoxide (TBHP) in dichloromethane giving alcohol (VIII). The reaction of (VIII) with methanesulfonyl chloride and then with LiBr affords the corresponding alkenyl bromide (IX), which is condensed with methyl acetoacetate (X) by means of NaH and n-BuLi in THF providing the ketoester (XI).

1 Ye, X.-Y.; Yang, D.; Xu, M.; Enantioselective total synthesis of (-)-triptolide, (-)-triptonide, (+)-triptophenolide, and (+)-triptoquinomide. J Org Chem 2000, 65, 7, 2208.
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) 37653 2-isopropylphenol 88-69-7 C9H12O 详情 详情
(II) 37654 1-isopropyl-2-(methoxymethoxy)benzene; (2-isopropylphenoxy)methyl methyl ether C11H16O2 详情 详情
(III) 37655 1-isopropyl-2-(methoxymethoxy)-3-methylbenzene; (2-isopropyl-6-methylphenoxy)methyl methyl ether C12H18O2 详情 详情
(IV) 12989 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene 870-63-3 C5H9Br 详情 详情
(V) 37656 1-isopropyl-2-(methoxymethoxy)-3-(4-methyl-3-pentenyl)benzene; [2-isopropyl-6-(4-methyl-3-pentenyl)phenoxy]methyl methyl ether C17H26O2 详情 详情
(VI) 37657 2-isopropyl-6-(4-methyl-3-pentenyl)phenol C15H22O 详情 详情
(VII) 37658 1-isopropyl-2-methoxy-3-(4-methyl-3-pentenyl)benzene; 2-isopropyl-6-(4-methyl-3-pentenyl)phenyl methyl ether C16H24O 详情 详情
(VIII) 37659 (E)-5-(3-isopropyl-2-methoxyphenyl)-2-methyl-2-penten-1-ol C16H24O2 详情 详情
(IX) 37660 2-[(E)-5-bromo-4-methyl-3-pentenyl]-6-isopropylphenyl methyl ether; 1-[(E)-5-bromo-4-methyl-3-pentenyl]-3-isopropyl-2-methoxybenzene C16H23BrO 详情 详情
(X) 11791 methyl 3-oxobutanoate; Methyl acetoacetate 105-45-3 C5H8O3 详情 详情
(XI) 35414 methyl (E)-9-(3-isopropyl-2-methoxyphenyl)-6-methyl-3-oxo-6-nonenoate C21H30O4 详情 详情
Extended Information