S-propyl 3-oxopentanethioate -Drug Synthesis Database

【结构式】

【分子编号】23704

【品名】S-propyl 3-oxopentanethioate

【CA登记号】

【分子式】C₈H₁₄O₂S

【分子量】174.26396

【元素组成】C 55.14% H 8.1% O 18.36% S 18.4%

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：(V)

Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III). Subsequent ring opening of (III) with propanethiol (IV), followed by decarboxylation provided S-propyl 3-oxothiovalerate (V). Propyl 3-amino-3-(m-chlorophenyl)-2-propenoate (VII) was prepared by reaction of (3-chlorobenzoyl)acetate (VI) with ammonium acetate in refluxing ethanol. Then, Hantzsch condensation of ketothioester (V), beta-enaminoester (VII), and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX). Finally, oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

参考文献中间体

合成目标

【1】 Li, A.-H.; Moro, S.; Melman, N.; Ji, X.D.; Jacobson, K.A.; Structure-activity relationships and molecular mod. J Med Chem 1998, 41, 17, 3186.

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)	14738	Meldrum's acid; 2,2-dimethyl-1,3-dioxane-4,6-dione；Malonic acid cyclic isopropylidene ester	2033-24-1	C₆H₈O₄	详情	详情
(II)	15967	propanoyl chloride; propionyl chloride	79-03-8	C₃H₅ClO	详情	详情
(III)	23689	2,2-dimethyl-5-propionyl-1,3-dioxane-4,6-dione		C₉H₁₂O₅	详情	详情
(IV)	23703	propylhydrosulfide; 1-propanethiol	107-03-9	C₃H₈S	详情	详情
(V)	23704	S-propyl 3-oxopentanethioate		C₈H₁₄O₂S	详情	详情
(VI)	23705	propyl 3-(3-chlorophenyl)-3-oxopropanoate		C₁₂H₁₃ClO₃	详情	详情
(VII)	23706	propyl (E)-3-amino-3-(3-chlorophenyl)-2-propenoate		C₁₂H₁₄ClNO₂	详情	详情
(VIII)	15966	propionaldehyde	123-38-6	C₃H₆O	详情	详情
(IX)	23708	propyl 2-(3-chlorophenyl)-4,6-diethyl-5-[(propylsulfanyl)carbonyl]-1,4-dihydro-3-pyridinecarboxylate		C₂₃H₃₀ClNO₃S	详情	详情
(X)	21891	2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil	118-75-2	C₆Cl₄O₂	详情	详情

Extended Information