8-oxaspiro[4.5]decane-7,9-dione -Drug Synthesis Database

【结构式】

【分子编号】34125

【品名】8-oxaspiro[4.5]decane-7,9-dione

【CA登记号】5662-95-3

【分子式】C₉H₁₂O₃

【分子量】168.19248

【元素组成】C 64.27% H 7.19% O 28.54%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The condensation of 1-(2-pyrimidinyl)piperazine (I) with 3-chloro-1-cyanopropane (II) by means of Na2CO3 in n-butanol gives 4-(2-pyrimidinyl)-1-(3-cyanopropyl)piperazine (III). This product is reduced with LiAlH4 or with H2 and Raney-Ni yielding 4-(2-pyrimidinyl)-1-(4-aminobutyl)piperazine (IV), which is finally condensed with 8-oxaspiro[4.5]decane-7,9-dione-(3,3-tetramethylene-glutaric anhydride) (V) in pyridine.

参考文献中间体

合成目标

【1】 Wu, Y.H.; et al.; N-(Heteroarcyclic)piperazizylalkylazaspiroalkanediones. DE 2057845; FR 2073406; GB 1332194; US 3717634 .
【2】 Wu, Y.H.; et al.; Psychosedative agents. 2. 8-(4-substituted-1-piperazinylalkyl)-8-azaspiro-[4,5]decane-7,9-diones. J Med Chem 1972, 15, 5, 477-479.
【3】 Castaner, J.; Thorpe, P.; Buspirone. Drugs Fut 1976, 1, 9, 409.

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)	11175	2-(1-Piperazinyl)pyrimidine; 2-Piperazinopyrimidine; N-(Pyrimidinyl)piperazine	20980-22-7	C₈H₁₂N₄	详情	详情
(II)	11179	4-Chlorobutanenitrile; 4-Chlorobutyronitrile	628-20-6	C₄H₆ClN	详情	详情
(III)	11180	4-[4-(2-Pyrimidinyl)piperazino]butanenitrile		C₁₂H₁₇N₅	详情	详情
(IV)	11181	4-[4-(2-Pyrimidinyl)piperazino]butylamine; 4-[4-(2-Pyrimidinyl)piperazino]-1-butanamine	33386-20-8	C₁₂H₂₁N₅	详情	详情
(V)	34125	8-oxaspiro[4.5]decane-7,9-dione	5662-95-3	C₉H₁₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

Condensation of piperazinyl dibenzoazepinone (X) with 3,3-tetramethyleneglutaric anhydride (XI) produced piperazide (XII). Further condensation of (XII) with arginine derivative (IX) using CDI yielded the title compound.

参考文献中间体

合成目标

【1】 Gaida, W.; Schnorrenberg, G.; Dollinger, H.; Doods, H.N.; Esser, F.; Rudolf, K.; Mihm, G. (Boehringer Ingelheim Pharma KG); Novel substd. amino acid derivs., process for their preparation and pharmaceutical compsns. containing them. DE 19816929 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IX)	37030	(2S)-2-amino-5-[[amino(imino)methyl]amino]-N-[2-(3,5-dioxo-1,2-diphenyl-1,2,4-triazolidin-4-yl)ethyl]pentanamide		C₂₂H₂₈N₈O₃	详情	详情
(X)	37031	11-(1-piperazinyl)-5,11-dihydro-6H-dibenzo[b,e]azepin-6-one		C₁₈H₁₉N₃O	详情	详情
(XI)	34125	8-oxaspiro[4.5]decane-7,9-dione	5662-95-3	C₉H₁₂O₃	详情	详情
(XII)	37032	2-(1-[2-oxo-2-[4-(6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl)-1-piperazinyl]ethyl]cyclopentyl)acetic acid		C₂₇H₃₁N₃O₄	详情	详情

Extended Information