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【结 构 式】 
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【分子编号】38832 【品名】6-(benzyloxy)-1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; benzyl 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-isoquinolinyl ether 【CA登记号】 |
【 分 子 式 】C24H23I2NO2 【 分 子 量 】611.2611 【元素组成】C 47.16% H 3.79% I 41.52% N 2.29% O 5.23% |
合成路线1
该中间体在本合成路线中的序号：(VI)Acid chloride (II) was prepared by treatment of 3,5-diiodo-4-methoxyphenylacetic acid with oxalyl chloride (1). Coupling of (II) with amine (IV), obtained by reducing its nitro precursor (III) with LiAlH4, under Schotten-Baumann conditions furnished amide (V). Bischler-Napieralski cyclization of amide (V), followed by NaBH4 reduction of the intermediate dihydroisoquinoline yielded tetrahydroisoquinoline (VI). Finally, deprotection of the benzyl ether of (VI) by refluxing in the presence of HCl provided the title compound.
| 【1】 Shams, G.; Feller, D.R.; Zheng, W.; Konkar, A.A.; Miller, D.D.; Nikulin, V.I.; Vansal, S.S.; 2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridines: Novel selective beta3-adrenoceptor agonists. J Med Chem 1999, 42, 12, 2287. |
| 【2】 Feller, D.R.; Miller, D.D.; He, Y.; Vansal, S.S.; Nikulin, V.I.; Synthesis and human beta-adrenoceptor activity of 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro. J Med Chem 2000, 43, 4, 591. |
| 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) | 35234 | 2-(3,5-diiodo-4-methoxyphenyl)acetic acid | C9H8I2O3 | 详情 | 详情 | |
| (II) | 35235 | 2-(3,5-diiodo-4-methoxyphenyl)acetyl chloride | C9H7ClI2O2 | 详情 | 详情 | |
| (III) | 38829 | benzyl 3-[(E)-2-nitroethenyl]phenyl ether; 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene | C15H13NO3 | 详情 | 详情 | |
| (IV) | 38830 | 3-(benzyloxy)phenethylamine; 2-[3-(benzyloxy)phenyl]-1-ethanamine | C15H17NO | 详情 | 详情 | |
| (V) | 38831 | N-[3-(benzyloxy)phenethyl]-2-(3,5-diiodo-4-methoxyphenyl)acetamide | C24H23I2NO3 | 详情 | 详情 | |
| (VI) | 38832 | 6-(benzyloxy)-1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; benzyl 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-isoquinolinyl ether | C24H23I2NO2 | 详情 | 详情 |