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【结 构 式】 
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【药物名称】Butaclamol hydrochloride, AY-23028 【化学名称】3alpha-tert-Butyl-2,3,4,4abeta,8,9,13balpha,14-octahydro-1H-benzo[6,7]cyclopenta-[1,2,3-de]pyrido[2,1-a]isoquinolin-3-ol hydrochloride 【CA登记号】36504-94-6, 51152-91-1 (free base) 【 分 子 式 】C25H32ClNO 【 分 子 量 】397.99289 |
【开发单位】Wyeth Pharmaceuticals (Originator) 【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS |
合成路线1
By reaction of methyl vinyl ketone (A) with 1,7,8,12b-tetrahydrobenzo[1,2] cyclohepta[3,4,5-d,e]isoquinoline hydrochloride (I) at 100 C to give trans-1,2,4,4a,8,9,13b,14-octahydro-3H-benzo[6,7]cyclopenta[1,2,3-d,e]pyrido[2,1-a]isoquinolin-3-one (II), m.p. 163-5 C, which is alkylated with tert-butyllithium in benzene.
| 【1】 Bruderlein, T.F.; Humber, L.G.; N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]amides. FR 2081498; GB 1341109; US 3657250; US 3914305 . |
| 【2】 Bruderlein, T.F.; et al.; The synthesis and sterreo-chemistry of teclamine hydrochloride, a novel psychotropic agent. Can J Chem 1974, 52, 2119. |
| 【3】 Bruderlein, T.F.; Humber, L.G.; Neuroleptic agents of the benzocycloheptapyridoisoquinoline series. 1. Synthesis and stereochemical ans structural requirements for activity of butaclamol and related compounds. J Med Chem 1975, 18, 2, 186. |
| 【4】 Chatterjee, S.S.; Castaner, J.; Butaclamol. Drugs Fut 1976, 1, 4, 171. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 30324 | 3-buten-2-one; methyl vinyl ketone | 78-94-4 | C4H6O | 详情 | 详情 |
| (I) | 40333 | 1,7,8,12b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline | C17H15N | 详情 | 详情 | |
| (II) | 40334 | (4aS,13bS)-1,2,4,4a,8,9,13b,14-octahydro-3H-benzo[6,7]cyclohepta[1,2,3-de]pyrido[2,1-a]isoquinolin-3-one | C21H21NO | 详情 | 详情 |