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【结 构 式】

【分子编号】56438

【品名】Methyl 3-hydroxy-2-methylenebutyrate

【CA登记号】

【 分 子 式 】C6H10O3

【 分 子 量 】130.1436

【元素组成】C 55.37% H 7.74% O 36.88%

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:(X)

Condensation of acetaldehyde with methyl acrylate (VIII) under Bayliss-Hillmann conditions gave rise to the allylic alcohol (IX). Bromination of (IX) using N-bromosuccinimide and dimethyl sulfide proceeded with rearrangement to the allyl bromide (X). This was then coupled with aldehyde (VII) in the presence of metallic tin and catalytic amounts of HOAc to produce, after acid-catalyzed cyclization, the target methylene butyrolactone derivative.

1 Gonzalez, A.G.; et al.; Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group. J Med Chem 2002, 45, 12, 2358.
2 Bermejo Barrera, J.; Hernandez Silva, M.; Alvarez de Mon, M.; Pivel Ranieri, J.P. (CSIC (Consejo Superior de Investigaciones Cientificas)); Derivs. of p-hydroxy phenyl propionic acid as antiproliferative agents. ES 2160093; WO 0172733 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 56437 3-(4-methoxyphenyl)propanal C10H12O2 详情 详情
(IX) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(X) 56438 Methyl 3-hydroxy-2-methylenebutyrate C6H10O3 详情 详情
(XI) 30136 methyl (Z)-2-(bromomethyl)-2-butenoate C6H9BrO2 详情 详情
Extended Information