4-propyldihydrofuran-2(3H)-one -Drug Synthesis Database

【结构式】

【分子编号】69043

【品名】4-propyldihydrofuran-2(3H)-one

【CA登记号】　

【分子式】C₇H₁₂O₂

【分子量】128.17108

【元素组成】C 65.6% H 9.44% O 24.97%

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：(XXV)

5-Hydroxy-4-propyl-2-furanone (V) is obtained by aldol condensation of glyoxylic acid (XXI) with valeraldehyde (XXII) in the presence of morpholine in heptane, followed by cyclization of the intermediate aldehyde acid under acidic conditions .
Preparation of iodoacyl chloride (VIII) starts with the conjugate addition of propylmagnesium bromide (XXIV) to 2-furanone (XXIII) in the presence of CuI and TMSCl in ethyl ether to produce 4-propylbutyrolactone (XXV), which undergoes lactone ring opening by means of iodotrimethylsilane in CH2Cl2, affording 3-(iodomethyl)hexanoic acid (XXVI), and finally, chlorination of acid (XXVI) with SOCl2 in benzene .

参考文献中间体

合成目标

【1】 Surtees, J., Lurquin, F., Diouf, O. (UCB SA). Process for preparing 2-oxo-1-pyrrolidine derivatives. CA 2538938, EP 1667967, JP 2007515387, US 2007100150, US 7629474, WO 2005028435.
【2】 Kenda, B.M., Matagne, A.C., Talaga, P.E. et al. Discovery of 4-substituted pyrrolidone butanamides as new agents with significant antiepileptic activity. J Med Chem 2004, 47(3): 530-49.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	58391	5-hydroxy-4-propyl-2(5H)-furanone；5-hydroxy-4-propyl-2-furanone	78920-10-2	C₇H₁₀O₃	详情	详情
(VIII)	69031	3-(iodomethyl)hexanoyl chloride		C₇H₁₂ClIO	详情	详情
(XXI)	15618	2-Oxoacetic acid; Glyoxylic Acid	298-12-4	C₂H₂O₃	详情	详情
(XXII)	13409	n-Valeraldehyde; Pentanal	110-62-3	C₅H₁₀O	详情	详情
(XXIII)	19267	2(5H)-furanone；furan-2(5H)-one；2-Buten-1,4-olide	497-23-4	C₄H₄O₂	详情	详情
(XXIV)	10790	Bromo(propyl)magnesium；bromopropylMagnesium；4-propylbutyrolactone；propylmagnesiumbromide；n-propylmagnesium bromide；Bromopropylmagnesium;	927-77-5	C₃H₇BrMg	详情	详情
(XXV)	69043	4-propyldihydrofuran-2(3H)-one		C₇H₁₂O₂	详情	详情
(XXVI)	69044	3-(iodomethyl)hexanoic acid		C₇H₁₃IO₂	详情	详情

Extended Information