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【结 构 式】 
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【分子编号】32084 【品名】3-[di(2-thienyl)methylene]octahydro-2H-quinolizine 【CA登记号】 |
【 分 子 式 】C18H21NS2 【 分 子 量 】315.50348 【元素组成】C 68.52% H 6.71% N 4.44% S 20.33% |
合成路线1
该中间体在本合成路线中的序号：(IX)The reaction of 2-piperidineethanol (I) with acrylonitrile (II) gives N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). The cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX). Finally, this compound is quaternirzed with methyl bromide in acetone.
| 【1】 Ogawa, N.; Matsubara, I.; Kato, H.; Kurata, S.; Koshinaka, E.; Yamagishi, K.; Kubo, S.; Studies on antispasmodics. I. Synthesis and anticholinergic activity of 1-, 2- and 3-diarylmethylenequinolizidine quaternary ammonium salts. Chem Pharm Bull 1979, 27, 6, 1454-63. |
| 【2】 Kato, H.; Koshinaka, E.; Ogawa, N.; Kurata, S.; Yamagishi, K.; Ishikuza, M. (Hokuriku Seiyaku Co., Ltd.); Substituted quinolizidine and indolizidine derivatives and the preparation thereof. BE 0866988; DE 2820687; FR 2390956; GB 1602927; JP 8034148 . |
| 【3】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Thorpe, P.J.; Tiquizium bromide. Drugs Fut 1982, 7, 9, 655. |
| 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) | 17614 | 2-(2-piperidinyl)-1-ethanol; 2-Piperidineethanol | 1484-84-0 | C7H15NO | 详情 | 详情 |
| (II) | 10847 | Acrylonitrile | 107-13-1 | C3H3N | 详情 | 详情 |
| (III) | 32078 | 3-[2-(2-hydroxyethyl)-1-piperidinyl]propanenitrile | C10H18N2O | 详情 | 详情 | |
| (IV) | 32079 | 3-[2-(2-chloroethyl)-1-piperidinyl]propanenitrile | C10H17ClN2 | 详情 | 详情 | |
| (V) | 32080 | octahydro-2H-quinolizine-3-carbonitrile | C10H16N2 | 详情 | 详情 | |
| (VI) | 32081 | ethyl octahydro-2H-quinolizine-3-carboxylate | C12H21NO2 | 详情 | 详情 | |
| (VII) | 32082 | bromo(2-thienyl)magnesium | 5713-61-1 | C4H3BrMgS | 详情 | 详情 |
| (VIII) | 32083 | octahydro-2H-quinolizin-3-yl[di(2-thienyl)]methanol | C18H23NOS2 | 详情 | 详情 | |
| (IX) | 32084 | 3-[di(2-thienyl)methylene]octahydro-2H-quinolizine | C18H21NS2 | 详情 | 详情 |