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

【结 构 式】

【分子编号】11368

【品名】(2-Methyl-1,3-dioxolan-2-yl)methanol

【CA登记号】

【 分 子 式 】C5H10O3

【 分 子 量 】118.1326

【元素组成】C 50.84% H 8.53% O 40.63%

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:(II)

This compound can be prepared in two related ways: 1) The condensation of diketene (I) with 2,2-(ethylenedioxy)propanol (II) by means of NaH in refluxing benzene gives 2,2-(ethylenedioxy)propyl acetylacetate (III), which is condensed with 2-nitrobenzaldehyde (IV) by means of piperidine and acetic acid in benzene, yielding 2,2-(ethylenedioxy)propyl 2-(2-nitrobenzylidene)acetoacetate (V). The cyclization of (V) with methyl 3-aminocrotonate (VI) in refluxing ethanol affords the protected dihydropyridine (VII), which is finally hydrolyzed with acetic acid in hot water. 2) The reaction of the acetoacetate (III), obtained as before, with ammonia in methanol gives the 3-aminocrotonate (VIII), which is cyclized with methyl 2-(2-nitrobenzylidene)acetoacetate (IX) in refluxing ethanol to afford the dihydropyridine (VII), already obtained.

1 Ohno, S.; Mizukoshi, K.; Komatsu, O.; Ichiara, K.; Morishima, T. (Maruko Seiyaku); Novel 1,4-dihydropyridines, especially useful as hypotensives. FR 2514761 .
2 Castaner, J.; Prous, J.; MPC-1304. Drugs Fut 1991, 16, 1, 25.
3 Sumita, T.; Nakamura, Y.; Ichihara, K.; Mizukoshi, K.; Komatsu, O.; Morishima, T.; Ohno, S.; Synthesis of asymmetric 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates with vasodilating and antihypertensive activities. Chem Pharm Bull 1986, 34, 4, 1589-606.
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) 11367 4-Methylene-2-oxetanone; Acetyl ketene 674-82-8 C4H4O2 详情 详情
(II) 11368 (2-Methyl-1,3-dioxolan-2-yl)methanol C5H10O3 详情 详情
(III) 11369 (2-methyl-1,3-dioxolan-2-yl)methyl 3-oxobutanoate C9H14O5 详情 详情
(IV) 11370 2-Nitrobenzaldehyde 552-89-6 C7H5NO3 详情 详情
(V) 11371 (2-methyl-1,3-dioxolan-2-yl)methyl (Z)-2-acetyl-3-(2-nitrophenyl)-2-propenoate C16H17NO7 详情 详情
(VI) 11372 Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate C5H9NO2 详情 详情
(VII) 11373 3-methyl 5-[(2-methyl-1,3-dioxolan-2-yl)methyl] 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate C21H24N2O8 详情 详情
(VIII) 11374 (2-methyl-1,3-dioxolan-2-yl)methyl (E)-3-amino-2-butenoate C9H15NO4 详情 详情
(IX) 11375 Methyl-2-(2-nitrobenzylidene)acetoacetate; methyl (Z)-2-acetyl-3-(2-nitrophenyl)-2-propenoate 39562-27-1 C12H11NO5 详情 详情
Extended Information