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【结 构 式】 
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【分子编号】28317 【品名】2-(4-methylphenyl)-1-(2-thienyl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C13H12OS 【 分 子 量 】216.30368 【元素组成】C 72.19% H 5.59% O 7.4% S 14.82% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 2-(4-methylphenyl)acetic acid (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with thiophene (III) by means SnCl4 yielding 2-(4-methylphenyl)-1-(2-thienyl)ethanone (IV). The reduction of (IV) with hydrazine and KOH in hot triethylene glycol affords 2-[2-(4-methylphenyl)ethyl]thiophene (V), which is condensed with 3,3-dimethylglutaric anhydride (VI), by means of AlCl3 in hot nitrobenzene giving the 5-oxopentanoic acid derivative (VII). The reduction of (VII) with hydrazine and KOH as before yields the pentanoic acid derivative (VIII), which is condensed with 4-(2,3,4-trimethoxybenzyl)piperazine (IX) by means of oxalyl chloride to afford the acyl piperazine (X). Finally, the amide group of (X) is reduced with LiAlH4 in ethyl ether.
| 【1】 Wierzbicki, M.; et al.; Amino derivatives of phenyl alkyl thiophene as inhibitors of bone resorption. Structure-activity relationship. Arzneim-Forsch Drug Res 1998, 48, 8, 840. |
| 【2】 Wierzbicki, M.; Sauveur, F.; Bonnet, J.; Brisset, M.; Tordjman, C. (ADIR et Cie.); Thiophene derivs., process for their preparation and pharmaceutical compsns. containing them. AU 9166901; EP 0429370; FR 2655043; JP 1991190872; US 5061704 . |
| 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) | 28316 | 2-(4-methylphenyl)acetic acid | 622-47-9 | C9H10O2 | 详情 | 详情 |
| (II) | 21017 | 2-(4-methylphenyl)acetyl chloride | 35675-44-6 | C9H9ClO | 详情 | 详情 |
| (III) | 13297 | Thiophene | 110-02-1 | C4H4S | 详情 | 详情 |
| (IV) | 28317 | 2-(4-methylphenyl)-1-(2-thienyl)-1-ethanone | C13H12OS | 详情 | 详情 | |
| (V) | 28318 | 2-(4-methylphenethyl)thiophene | C13H14S | 详情 | 详情 | |
| (VI) | 25549 | 4,4-dimethyldihydro-2H-pyran-2,6(3H)-dione | 4160-82-1 | C7H10O3 | 详情 | 详情 |
| (VII) | 28319 | 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]-5-oxopentanoic acid | C20H24O3S | 详情 | 详情 | |
| (VIII) | 28320 | 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]pentanoic acid | C20H26O2S | 详情 | 详情 | |
| (IX) | 24354 | 2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether | C14H22N2O3 | 详情 | 详情 | |
| (X) | 28321 | 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone | C34H46N2O4S | 详情 | 详情 |