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【结 构 式】 
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【分子编号】64850 【品名】methyl 3-chloro-5,6-dihydroxy-1-benzothiophene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C10H7ClO4S 【 分 子 量 】258.68188 【元素组成】C 46.43% H 2.73% Cl 13.71% O 24.74% S 12.4% |
合成路线1
该中间体在本合成路线中的序号：(IV)Treatment of 3,4-methylenedioxycinnamic acid (I) with thionyl chloride and pyridine gives the benzothiophene-2-carbonyl chloride (II), which is reacted with methanol in toluene to produce the methyl ester (III). Cleavage of the methylenedioxy group of (III) with BBr3 affords the dihydroxy derivative (IV), which upon alkylation with 4-(phenylsulfanyl)benzyl chloride (V) yields the diether derivative (VI). The ester function of (VI) is then reduced by LiAlH4 to the primary alcohol (VII), which is further oxidized to aldehyde (VIII) by means of MnO2 in toluene. Substitution of the chlorine atom of (VIII) with 4-chlorophenol (IX) in the presence of NaH furnishes the chlorophenyl ether (X).
| 【1】 De Nanteuil, G.; Lila-Ambroise, C.; Rupin, A.; Vallez, M.-O.; Verbeuren, T.J.; New fibrinolytic agents: Benzothiophene derivatives as inhibitors of the t-PA-PAI-1 complex formation. Bioorg Med Chem Lett 2003, 13, 10, 1705. |
| 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) | 11634 | (E)-3-(1,3-Benzodioxol-5-yl)-2-propenoic acid; 3,4-(Methylenedioxy)cinnamic acid | 2373-80-0 | C10H8O4 | 详情 | 详情 |
| (II) | 64848 | 7-chlorothieno[2,3-f][1,3]benzodioxole-6-carbonyl chloride | C10H4Cl2O3S | 详情 | 详情 | |
| (III) | 64849 | methyl 7-chlorothieno[2,3-f][1,3]benzodioxole-6-carboxylate | C11H7ClO4S | 详情 | 详情 | |
| (IV) | 64850 | methyl 3-chloro-5,6-dihydroxy-1-benzothiophene-2-carboxylate | C10H7ClO4S | 详情 | 详情 | |
| (V) | 31094 | 1-(chloromethyl)-4-(phenylsulfanyl)benzene; 4-(chloromethyl)phenyl phenyl sulfide | C13H11ClS | 详情 | 详情 | |
| (VI) | 64851 | methyl 3-chloro-5,6-bis{[4-(phenylsulfanyl)benzyl]oxy}-1-benzothiophene-2-carboxylate | C36H27ClO4S3 | 详情 | 详情 | |
| (VII) | 64852 | (3-chloro-5,6-bis{[4-(phenylsulfanyl)benzyl]oxy}-1-benzothiophen-2-yl)methanol | C35H27ClO3S3 | 详情 | 详情 | |
| (VIII) | 64853 | 3-chloro-5,6-bis{[4-(phenylsulfanyl)benzyl]oxy}-1-benzothiophene-2-carbaldehyde | C35H25ClO3S3 | 详情 | 详情 | |
| (IX) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (X) | 64854 | 3-(4-chlorophenoxy)-5,6-bis{[4-(phenylsulfanyl)benzyl]oxy}-1-benzothiophene-2-carbaldehyde | C41H29ClO4S3 | 详情 | 详情 |