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【结 构 式】

【分子编号】35924

【品名】10-bromo-5H-dibenzo[a,d]cyclohepten-5-one

【CA登记号】

【 分 子 式 】C15H9BrO

【 分 子 量 】285.13986

【元素组成】C 63.18% H 3.18% Br 28.02% O 5.61%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The reaction of 10-bromo-5H-dibenzo[a,d]cyclohepten-5-one (I) with N-methylpiperazine (A) by means of potassium tert-butoxide in refluxing tert-butanol gives 10-(N-methylpiperazin-1-yl)-5H-dibenzo[a,d]cyclohepten-5-one (II), which by treatment first with methyllithium in ether and then with refluxing ethanolic HCl is converted into 5-methylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-one (III). The reaction of (III) with hydroxylamine in refluxing methanol yields 5-methylene-10-hydroxyimino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (IV), which is reduced with sodium cyanoborohydride in methanol to afford 5-methylene-10-hydroxamino-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (V). The internal reaction of (V) in refluxing xylene gives 5-(hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (V), which is reduced with Zn in hot acetic acid.

1 Evans, B.E.; Engelhardt, E.L.; Remy, D.C.; Britcher, S.F.; Andderson, P.S.; Colton, C.D.; Christy, M.E.; Transannular reaction of dibenzo[a,d]cycloalkenes. 1. Synthesis of dibenzo[a,d]cycloocten-6,12-imines and dibenzo[a,d]cyclohepten-5,10-imines. J Org Chem 1979, 44, 18, 3117-27.
2 Thorpe, P.J.; Castaner, J.; Serradell, M.N.; Blancafort, P.; MK-801. Drugs Fut 1983, 8, 2, 120.
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) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(I) 35924 10-bromo-5H-dibenzo[a,d]cyclohepten-5-one C15H9BrO 详情 详情
(II) 35925 10-(4-methyl-1-piperazinyl)-5H-dibenzo[a,d]cyclohepten-5-one C20H20N2O 详情 详情
(III) 35926 5-methylene-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one C16H12O 详情 详情
(IV) 35927 5-methylene-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one oxime C16H13NO 详情 详情
(V) 35928 10-(hydroxyamino)-5-methylene-5H-dibenzo[a,d]cycloheptene; N-(5-methylene-5H-dibenzo[a,d]cyclohepten-10-yl)hydroxylamine C16H13NO 详情 详情
(VI) 35929 16-azatetracyclo[7.6.1.0(2,7).0(10,15)]hexadeca-2,4,6,10,12,14-hexaen-1-ylmethanol C16H15NO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

Intermediate (III) can be obtained as follows: The reaction of (I) with piperidine (B) by means of potassium tertbutoxide in refluxing tert-butanol gives 10-(1-piperidyl)-5H-dibenzo[a,d]cyclohepten-5-one (XII), which by reaction with methyllithium in ether is converted into 5-hydroxy-5-methyl-10-(1-piperidyl)-5H-dibenzo[a,d]cycloheptene (XIII). Finally, the dehydration of (XIII) in refluxing ethanolic HCl yields (III), already obtained.

1 Anderson, P.S.; Christy, M.E.; Evans, B.E.; ES 473492 .
2 Thorpe, P.J.; Castaner, J.; Serradell, M.N.; Blancafort, P.; MK-801. Drugs Fut 1983, 8, 2, 120.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10158 Piperidine 110-89-4 C5H11N 详情 详情
(I) 35924 10-bromo-5H-dibenzo[a,d]cyclohepten-5-one C15H9BrO 详情 详情
(III) 35926 5-methylene-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-one C16H12O 详情 详情
(XII) 35930 10-(1-piperidinyl)-5H-dibenzo[a,d]cyclohepten-5-one C20H19NO 详情 详情
(XIII) 35931 5-methyl-10-(1-piperidinyl)-5H-dibenzo[a,d]cyclohepten-5-ol C21H23NO 详情 详情
Extended Information