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【结 构 式】

【分子编号】13919

【品名】6-[(2R)Oxiranylmethoxy]-2(1H)-quinolinone

【CA登记号】

【 分 子 式 】C12H11NO3

【 分 子 量 】217.22428

【元素组成】C 66.35% H 5.1% N 6.45% O 22.1%

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:(IV)

The synthesis of the (+)-(R)-isomer of OPC-18790 has been published: The condensation of 6-hydroxyquinolin-2(1H)-one (I) with (S)-(+)-epichlorohydrin (II) by means of triethylamine in methanol gives (S)-(+)-6-(3-chloro-2-hydroxypropoxy)quinolin-2(1H)-one (III), which by reaction with KOH in isopropanol/water yields the (R)-(-)-epoxide (IV). Finally, this compound is condensed with 3,4-dimethoxybenzylamine (V) by heating its mixture at 80 C. The (+)-(R)-isomer is about 10-fold more potent than the (-)-(S)-isomer.

1 Fujioka, T.; Teramoto, S.; Tominaga, M.; Mori, T.; Sumida, T.; Yabuuchi, Y.; Tsujimi, S.; Takemoto, K.; Hosokawa, T.; Synthesis and biological activities of optically active 6-[3-(3,4-dimethox ybenzylamino)-2 hydroxypropoxy]-2(1H)-quinolinone (OPC-18790). Chem Pharm Bull 1996, 44, 8, 1596.
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) 13913 6-Hydroxy-2(1H)-quinolinone C9H7NO2 详情 详情
(II) 13917 (S)-Epichlorohydrin; (2S)-2-(Chloromethyl)oxirane;(S)-(+)-epichlorohydrin 67843-74-7 C3H5ClO 详情 详情
(III) 13918 6-[[(2S)-3-Chloro-2-hydroxypropyl]oxy]-2(1H)-quinolinone C12H12ClNO3 详情 详情
(IV) 13919 6-[(2R)Oxiranylmethoxy]-2(1H)-quinolinone C12H11NO3 详情 详情
(V) 13920 (3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine 5763-61-1 C9H13NO2 详情 详情
Extended Information