• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】48457

【品名】4-(2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran-4-yl)-2,6-diiodophenol

【CA登记号】

【 分 子 式 】C22H14I2O2S

【 分 子 量 】596.2269

【元素组成】C 44.32% H 2.37% I 42.57% O 5.37% S 5.38%

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:(IX)

Oxidation of 2,3-dimethylfuran (I) under Vilsmeier conditions with POCl3 in DMF affords aldehyde (II), which is then condensed with benzothiophene (III) by means of n-BuLi in THF to provide secondary alcohol (IV). Reduction of (IV) under Nutaitis conditions with NaBH4 and TFA in THF yields methylene congener (V), which is then treated with p-anisoyl chloride (VI) under Friedel-Crafts conditions with SnCl4 in CS2 to give 1-oxa-9-thiacyclopenta[b]fluorene heterocycle (VII). Demethylation of methyl ether (VII) with BBr3 in CH2Cl2 affords phenol (VIII), which is then bis-iodinated with molecular iodine and NaOH in MeOH to yield di-iodo phenol (IX). Compound (IX) is then condensed with (S)-2-hydroxy-3-phenylpropionic acid (X) under Mitsunobu conditions with DEAD and PPh3 in benzene to furnish (R)-2-benzyl-acetic acid derivative (XI), which is finally hydrolyzed by treatment with KOH in H2O/dioxane to provide the desired product.

1 Sredy, j.; Seesteller, L.; Li, Z.; Sawicki, D.R.; Wrobel, J.; Sullivan, D.; Synthesis and PTP1B inhibition of novel 4-aryl-1-oxa-9-thiacyclopenta[b]fluorenes. Bioorg Med Chem Lett 2000, 10, 14, 1535.
2 Li, Z.; Wrobel, J.E. (American Home Products Corp.); 4-Aryl-1-oxa-9-thia-cyclopenta[b]fluorenes. US 6057316 .
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) 48451 2,3-Dimethylfuran 14920-89-9 C6H8O 详情 详情
(II) 48452 4,5-Dimethyl-2-furaldehyde; 4,5-Dimethylfurfural C7H8O2 详情 详情
(III) 25578 1-benzothiophene 95-15-8 C8H6S 详情 详情
(IV) 48453 1-benzothiophen-2-yl(4,5-dimethyl-2-furyl)methanol C15H14O2S 详情 详情
(V) 48454 5-(1-benzothiophen-2-ylmethyl)-2,3-dimethylfuran C15H14OS 详情 详情
(VI) 22671 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride 100-07-2 C8H7ClO2 详情 详情
(VII) 48455 4-(2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran-4-yl)phenyl methyl ether; 4-(4-methoxyphenyl)-2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran C23H18O2S 详情 详情
(VIII) 48456 4-(2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran-4-yl)phenol C22H16O2S 详情 详情
(IX) 48457 4-(2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran-4-yl)-2,6-diiodophenol C22H14I2O2S 详情 详情
(X) 39252 methyl (2S)-2-hydroxy-3-phenylpropanoate C10H12O3 详情 详情
(XI) 48458 methyl (2R)-2-[4-(2,3-dimethyl[1]benzothieno[3,2-f][1]benzofuran-4-yl)-2,6-diiodophenoxy]-3-phenylpropanoate C32H24I2O4S 详情 详情
Extended Information