propyl (E)-3-amino-3-phenyl-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】23693

【品名】propyl (E)-3-amino-3-phenyl-2-propenoate

【CA登记号】

【分子式】C₁₂H₁₅NO₂

【分子量】205.25664

【元素组成】C 70.22% H 7.37% N 6.82% O 15.59%

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：(VII)

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 ethanethiol (IV), followed by decarboxylation provided S-ethyl 3-oxothiovalerate (V). Propyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (VI) with ammonium acetate in refluxing ethanol. Then, Hantzsch condensation of ketothioester (V), beta-enaminoester (VII), and butyraldehyde (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
(B)	21391	D-aspartic acid; (2R)-2-aminobutanedioic acid	1783-96-6	C₄H₇NO₄	详情	详情
(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)	23712	1-ethanethiol; ethylhydrosulfide	75-08-1	C₂H₆S	详情	详情
(V)	23696	S-ethyl 3-oxopentanethioate		C₇H₁₂O₂S	详情	详情
(VI)	23692	propyl 3-oxo-3-phenylpropanoate		C₁₂H₁₄O₃	详情	详情
(VII)	23693	propyl (E)-3-amino-3-phenyl-2-propenoate		C₁₂H₁₅NO₂	详情	详情
(VIII)	23694	butyraldehyde	123-72-8	C₄H₈O	详情	详情
(IX)	23695	propyl 6-ethyl-5-[(ethylsulfanyl)carbonyl]-2-phenyl-4-propyl-1,4-dihydro-3-pyridinecarboxylate		C₂₃H₃₁NO₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

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 ethanethiol (IV), followed by decarboxylation provided S-ethyl 3-oxothiovalerate (V). Ethyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (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)	23712	1-ethanethiol; ethylhydrosulfide	75-08-1	C₂H₆S	详情	详情
(V)	23696	S-ethyl 3-oxopentanethioate		C₇H₁₂O₂S	详情	详情
(VI)	23692	propyl 3-oxo-3-phenylpropanoate		C₁₂H₁₄O₃	详情	详情
(VII)	23693	propyl (E)-3-amino-3-phenyl-2-propenoate		C₁₂H₁₅NO₂	详情	详情
(VIII)	15966	propionaldehyde	123-38-6	C₃H₆O	详情	详情
(IX)	23699	ethyl 4,6-diethyl-5-[(ethylsulfanyl)carbonyl]-2-phenyl-1,4-dihydro-3-pyridinecarboxylate		C₂₁H₂₇NO₃S	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