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

【结构式】

【分子编号】23715

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

【CA登记号】

【分子式】C₁₁H₁₃NO₂

【分子量】191.22976

【元素组成】C 69.09% H 6.85% N 7.32% O 16.73%

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 butyryl chloride (II) in the presence of pyridine gave butyryl derivative (III). Subsequent ring opening of (III) with ethanethiol (IV), followed by decarboxylation provided S-ethyl 3-oxothiocaproate (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), b-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)	10792	Butanoyl chloride; Butyryl chloride	141-75-3	C₄H₇ClO	详情	详情
(III)	23711	5-butyryl-2,2-dimethyl-1,3-dioxane-4,6-dione		C₁₀H₁₄O₅	详情	详情
(IV)	23712	1-ethanethiol; ethylhydrosulfide	75-08-1	C₂H₆S	详情	详情
(V)	23713	S-ethyl 3-oxohexanethioate		C₈H₁₄O₂S	详情	详情
(VI)	10004	Ethyl 3-oxo-3-phenylpropanoate; Benzoylacetic acid, ethyl ester	94-02-0	C₁₁H₁₂O₃	详情	详情
(VII)	23715	ethyl (E)-3-amino-3-phenyl-2-propenoate		C₁₁H₁₃NO₂	详情	详情
(VIII)	15966	propionaldehyde	123-38-6	C₃H₆O	详情	详情
(IX)	23716	ethyl 4-ethyl-5-[(ethylsulfanyl)carbonyl]-2-phenyl-6-propyl-1,4-dihydro-3-pyridinecarboxylate		C₂₂H₂₉NO₃S	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

合成路线2

该中间体在本合成路线中的序号：(III)

Pyridine (V) was prepared by Hantsch synthesis upon condensation of ketothioester (I), aldehyde (II) and enamino ester (III), followed by oxidative aromatization of the resulting dihydropyridine (IV) with chloranil, according to a reported method. N-Alkylation of pyridine (V) with iodomethane in hot nitromethane in a sealed tube under pressure furnished the title pyridinium salt.

参考文献中间体

合成目标

【1】 Li, A.-H.; Xie, R.; melman, N.; Ji, X.-D.; Stiles, G.L.; Olah, M.E.; Jacobson, K.A.; Selective A3 adenosine receptor antagonists: Water-soluble 3,5-diacyl-1,2,4-trialkylpyridinium salts and their oxidative generation from dihydropyridine precursors. J Med Chem 1999, 42, 20, 4232.

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)	23696	S-ethyl 3-oxopentanethioate		C₇H₁₂O₂S	详情	详情
(II)	15966	propionaldehyde	123-38-6	C₃H₆O	详情	详情
(III)	23715	ethyl (E)-3-amino-3-phenyl-2-propenoate		C₁₁H₁₃NO₂	详情	详情
(IV)	23699	ethyl 4,6-diethyl-5-[(ethylsulfanyl)carbonyl]-2-phenyl-1,4-dihydro-3-pyridinecarboxylate		C₂₁H₂₇NO₃S	详情	详情
(V)	43762	ethyl 4,6-diethyl-5-[(ethylsulfanyl)carbonyl]-2-phenylnicotinate		C₂₁H₂₅NO₃S	详情	详情

Extended Information