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【结 构 式】

【分子编号】58425

【品名】(10S,11R)-11-allyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol

【CA登记号】

【 分 子 式 】C18H18O

【 分 子 量 】250.34032

【元素组成】C 86.36% H 7.25% O 6.39%

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:(IV)

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.

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
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