1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one -Drug Synthesis Database

【结构式】

【分子编号】27190

【品名】1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one

【CA登记号】

【分子式】C₉H₁₄OSi

【分子量】166.29506

【元素组成】C 65% H 8.49% O 9.62% Si 16.89%

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：(III)

The reaction of cyclopropanecarbonyl chloride (I) with bis(trimethylsilyl)acetylene (II) gives 1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one (III), which is reduced with NaBH4 and CeCl3 in methanol to the corresponding propynol (IV). The condensation of (IV) with 3-hydroxy-4,5-dimethoxybenzaldehyde (V) by means of triphenylphosphine and dimethyl azodicarboxylate in toluene yields the expected propynyl ether (VI), which is cyclized in N,N-diethylaniline at 200 C affording 2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-carbaldehyde (VII). The condensation of (VII) with 3-anilinopropionitrile (VIII) by means of potassium tert-butoxide in DMSO gives the acrylonitrile (IX), which is finally cyclized with guanidine (X) by means of potassium tert-butoxide in ethanol. (1)

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castañer, J.; Rabasseda, X.; Iclaprim. Drugs Fut 2004, 29, 3, 220.
【2】 Masciadri, R. (F. Hoffmann-La Roche AG); Diaminopyrimidines, pharmaceutical compsns. containing them and their use as antibacterial. EP 0866791; JP 2000501399; US 5773446; WO 9720839 .

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)	14061	Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride	4023-34-1	C₄H₅ClO	详情	详情
(II)	27189	trimethyl[2-(trimethylsilyl)ethynyl]silane	14630-40-1	C₈H₁₈Si₂	详情	详情
(III)	27190	1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one		C₉H₁₄OSi	详情	详情
(IV)	27191	1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-ol		C₉H₁₆OSi	详情	详情
(V)	27192	3-hydroxy-4,5-dimethoxybenzaldehyde		C₉H₁₀O₄	详情	详情
(VI)	27193	3-[[1-cyclopropyl-3-(trimethylsilyl)-2-propynyl]oxy]-4,5-dimethoxybenzaldehyde		C₁₈H₂₄O₄Si	详情	详情
(VII)	27194	2-cyclopropyl-7,8-dimethoxy-2H-chromene-5-carbaldehyde		C₁₅H₁₆O₄	详情	详情
(VIII)	27195	3-anilinopropanenitrile	1075-76-9	C₉H₁₀N₂	详情	详情
(IX)	27196	3-(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)-2-[(phenylimino)methyl]propanenitrile		C₂₄H₂₄N₂O₃	详情	详情
(X)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of cyclopropanecarbonyl chloride (I) with bis(trimethylsilyl)acetylene (II) gives 1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one (III), which is reduced with NaBH4 and CeCl3 in methanol to the corresponding propynol (IV). The condensation of propynol (IV) with 3-hydroxy-4,5-dimethoxybenzoic acid methyl ester (XI) by means of triphenylphosphine and dimethyl azodicarboxylate in toluene yields the expected propynyl ether (XII), which is cyclized in N,N-diethylaniline at 200 C affording 2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-carboxylic acid methyl ester (XIII). Finally, this compound is reduced with NaAlH2(OCH2CH2)2 and morpholine in toluene to give the previously described 2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-carbaldehyde (VII). The condensation of (VII) with 3-anilinopropionitrile (VIII) by means of potassium tert-butoxide in DMSO gives the acrylonitrile (IX), which is finally cyclized with guanidine (X) by means of potassium tert-butoxide in ethanol.

参考文献中间体

合成目标

【1】 Masciadri, R. (F. Hoffmann-La Roche AG); Diaminopyrimidines, pharmaceutical compsns. containing them and their use as antibacterial. EP 0866791; JP 2000501399; US 5773446; WO 9720839 .

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)	14061	Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride	4023-34-1	C₄H₅ClO	详情	详情
(II)	27189	trimethyl[2-(trimethylsilyl)ethynyl]silane	14630-40-1	C₈H₁₈Si₂	详情	详情
(III)	27190	1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-one		C₉H₁₄OSi	详情	详情
(IV)	27191	1-cyclopropyl-3-(trimethylsilyl)-2-propyn-1-ol		C₉H₁₆OSi	详情	详情
(VII)	27194	2-cyclopropyl-7,8-dimethoxy-2H-chromene-5-carbaldehyde		C₁₅H₁₆O₄	详情	详情
(VIII)	27195	3-anilinopropanenitrile	1075-76-9	C₉H₁₀N₂	详情	详情
(IX)	27196	3-(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)-2-[(phenylimino)methyl]propanenitrile		C₂₄H₂₄N₂O₃	详情	详情
(X)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(XI)	27197	methyl 3-hydroxy-4,5-dimethoxybenzoate		C₁₀H₁₂O₅	详情	详情
(XII)	27198	methyl 3-[[1-cyclopropyl-3-(trimethylsilyl)-2-propynyl]oxy]-4,5-dimethoxybenzoate		C₁₉H₂₆O₅Si	详情	详情
(XIII)	27199	methyl 2-cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylate		C₁₆H₁₈O₅	详情	详情

Extended Information