• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【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

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.

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.

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