3-isopropyl-4-methylpentanoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】39319

【品名】3-isopropyl-4-methylpentanoyl chloride

【CA登记号】

【分子式】C₉H₁₇ClO

【分子量】176.68608

【元素组成】C 61.18% H 9.7% Cl 20.07% O 9.06%

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：(VI)

Addition of vinylmagnesium bromide to diisopropyl ketone (I) produced carbinol (II). Subsequent oxidation of (II) with pyridinium chlorochromate gave unsaturated aldehyde (III), which was further hydrogenated to the saturated aldehyde (IV). Optionally, oxidation with sodium chlorite produced carboxylic acid (V), which was converted to acid chloride (VI) using oxalyl chloride and pyridine.

参考文献中间体

合成目标

【1】 Marquez, V.E.; Bienfait, B.; Lewin, N.E.; Benzaria, S.; Bhattacharyya, D.K.; Lee, J.; Nacro, K.; Han, K.-C.; Kang, J.-H.; Blumberg, P.M.; Conformationally constrained analogues of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C?. J Med Chem 2000, 43, 5, 921.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	16524	bromo(vinyl)magnesium	1826-67-1	C₂H₃BrMg	详情	详情
(I)	39314	2,4-dimethyl-3-pentanone	565-80-0	C₇H₁₄O	详情	详情
(II)	39315	3-isopropyl-4-methyl-1-penten-3-ol		C₉H₁₈O	详情	详情
(III)	39316	3-isopropyl-4-methyl-2-pentenal		C₉H₁₆O	详情	详情
(IV)	39317	3-isopropyl-4-methylpentanal		C₉H₁₈O	详情	详情
(V)	39318	3-isopropyl-4-methylpentanoic acid		C₉H₁₈O₂	详情	详情
(VI)	39319	3-isopropyl-4-methylpentanoyl chloride		C₉H₁₇ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Aldol condensation of silylated lactone (VII) with aldehyde (IV) gave hydroxy lactone (VIII). Subsequent hydroxyl group mesylation followed by elimination in the presence of DBU generated alkylidene lactone (IXa-b) as a mixture of geometric isomers, which were separated by chromatography. Desilylation of (IX) to afford diol (X) was achieved by means of HF/pyridine. Finally, monoacylation of (X) with acid chloride (VI) and pyridine furnished the target ester.

参考文献中间体

合成目标

【1】 Marquez, V.E.; Bienfait, B.; Lewin, N.E.; Benzaria, S.; Bhattacharyya, D.K.; Lee, J.; Nacro, K.; Han, K.-C.; Kang, J.-H.; Blumberg, P.M.; Conformationally constrained analogues of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C?. J Med Chem 2000, 43, 5, 921.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IXa)	39322	5,5-bis([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-[(E)-3-isopropyl-4-methylpentylidene]dihydro-2(3H)-furanone	C₄₇H₆₂O₄Si₂	详情	详情
(IXb)	39323	5,5-bis([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-[(Z)-3-isopropyl-4-methylpentylidene]dihydro-2-furanone	C₄₇H₆₂O₄Si₂	详情	详情
(IV)	39317	3-isopropyl-4-methylpentanal	C₉H₁₈O	详情	详情
(VI)	39319	3-isopropyl-4-methylpentanoyl chloride	C₉H₁₇ClO	详情	详情
(VII)	39320	5,5-bis([[tert-butyl(diphenyl)silyl]oxy]methyl)dihydro-2(3H)-furanone	C₃₈H₄₆O₄Si₂	详情	详情
(VIII)	39321	5,5-bis([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(1-hydroxy-3-isopropyl-4-methylpentyl)dihydro-2(3H)-furanone	C₄₇H₆₄O₅Si₂	详情	详情
(X)	39324	5,5-bis(hydroxymethyl)-3-[(Z)-3-isopropyl-4-methylpentylidene]dihydro-2-furanone	C₁₅H₂₆O₄	详情	详情

Extended Information