5H-dibenzo[a,d]cycloheptene -Drug Synthesis Database

【结构式】

【分子编号】58423

【品名】5H-dibenzo[a,d]cycloheptene

【CA登记号】

【分子式】C₁₅H₁₂

【分子量】192.26028

【元素组成】C 93.71% H 6.29%

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：(II)

Reduction of dibenzosuberenone (I) with in situ generated AlH3 affords dibenzocycloheptene (II). Subsequent epoxidation of (II) employing m-chloroperbenzoic acid gives the dibenzocycloheptaoxirane (III) (1). Epoxide ring opening in (III) with allylmagnesium bromide produces the trans alcohol (IV). Bromination of the double bond of (IV) with pyridinium tribromide leads to the trans-fused tetrahydrofuran derivative (V) as a mixture of 4 diastereoisomers. Then, substitution of the bromide ion of (V) with dimethylamine, followed by chromatographic separation of the isomers provides the target compound.

参考文献中间体

合成目标

【1】 Alonso, J.M.; Andres, J.I.; Cid, J.M.; et al.; Synthesis of 2-aminomethyl-3,3a,8,12b-tetrahydro-2H-dibenzocyclohepta[1,2-b]furan derivatives as potential anxiolytic agents. Drugs Fut 2002, 27, Suppl. A.
【2】 Gil-Lopetegui, P.; Fernandez-Gadea, F.J.; Meert, T.F. (Janssen Pharmaceutica NV); Substd. tetracyclic tetrahydrofuran derivs.. EP 0892793; JP 2000508327; WO 9738991 .

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)	29151	5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberenone	2222-33-5	C₁₅H₁₀O	详情	详情
(II)	58423	5H-dibenzo[a,d]cycloheptene		C₁₅H₁₂	详情	详情
(III)	58424	6,10b-dihydro-1aH-dibenzo[3,4:6,7]cyclohepta[1,2-b]oxirene		C₁₅H₁₂O	详情	详情
(IV)	58425	(10S,11R)-11-allyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol		C₁₈H₁₈O	详情	详情
(V)	58426	(3aR,12bS)-2-(bromomethyl)-3,3a,8,12b-tetrahydro-2H-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan		C₁₈H₁₇BrO	详情	详情

Extended Information