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【结 构 式】

【分子编号】63809

【品名】isopropyl 3-isopropoxy-5-methoxy-1-benzothiophene-2-carboxylate

【CA登记号】

【 分 子 式 】C16H20O4S

【 分 子 量 】308.3984

【元素组成】C 62.31% H 6.54% O 20.75% S 10.4%

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-2)

Alternate routes to the key benzo[b]thiophene ester intermediates (IV) are described: 1) Alkylation of the thiol ester (I) yields the diester (II), and a Dieckmann condensation of (II) with base provides the benzo[b]thiophene enol ester (III). Alkylation of (III) with 2-bromopropane then yields the ester intermediate (IV, R = CH3). 2) A shorter route to (IV) begins with cyclization of the cinnamic acid derivative (V) with thionyl choride (2) to give the chloro acid chloride (VI). Reaction of (VI) with the potassium salt of 2-propanol yields the ester (IV, R = CH(CH3)2).

1 Higa, T.; Krubsack, A.J.; Oxidations by thionyl chloride. VI. Mechanism of the reaction with cinnamic acids. J Org Chem 1975, 40, 3037-45.
2 Johnson, J.; Tramondozzi; Bennet, O.F.; Synthesis of 2-methoxydibenzo[b,f][1,4]thiazapin-11(10H)-one 5,5-dioxide. Org Prep Proced Int 1974, 6, 287-93.
3 Unangst, P.C.; Connor, D.T.; Low, J.E.; Conroy, M.C.; CI-959. Drugs Fut 1994, 19, 1, 17.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV-1) 13890 methyl 3-isopropoxy-5-methoxy-1-benzothiophene-2-carboxylate C14H16O4S 详情 详情
(IV-2) 63809 isopropyl 3-isopropoxy-5-methoxy-1-benzothiophene-2-carboxylate C16H20O4S 详情 详情
(I) 13887 methyl 5-methoxy-2-sulfanylbenzoate C9H10O3S 详情 详情
(II) 13888 methyl 5-methoxy-2-[(2-methoxy-2-oxoethyl)sulfanyl]benzoate C12H14O5S 详情 详情
(III) 13889 methyl 3-hydroxy-5-methoxy-1-benzothiophene-2-carboxylate C11H10O4S 详情 详情
(V) 13891 (E)-3-(3-Methoxyphenyl)-2-propenoic acid; m-Methoxycinnamic acid 6099-04-3 C10H10O3 详情 详情
(VI) 13892 3-Chloro-5-methoxy-1-benzothiophene-2-carbonyl chloride C10H6Cl2O2S 详情 详情
Extended Information