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HRID 1017941作成日:2026年10月25日

Diethyl (cyanomethyl)phosphonate → 3-(4-Biphenylyl)-3-(3,4-dimethoxyphenyl)acrylonitrile

https://huagongshe.com/reaction/1017941

反応式

関与物質

役割名称HCID仕込み量
反応物Diethyl (cyanomethyl)phosphonateHCID 75676—
反応物3,4-Dimethoxy-4'-phenylbenzophenoneHCID 2288732—
反応物Lithium HexamethyldisilazideHCID 2733832—
反応物Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylateHCID 9820154—
生成物3-(4-Biphenylyl)-3-(3,4-dimethoxyphenyl)acrylonitrileHCID 53981481—

反応手順

3-(4-Biphenylyl)-3-(3,4-dimethoxyphenyl)acrylonitrile was prepared analogously to methyl 3,3-bis-(3′,4′-dimethoxyphenyl)acrylate using 3,4-dimethoxy-4′-phenylbenzophenone (2.33 g, 7.32 mmol), diethylcyanomethylphosphonate (1.5 mL, 8.1 mmol) and lithium hexamethyldisilazide (8.1 mL, 8.1 mmol, 1 M) with a reaction time of 22 hours. The crude product was purified by chromatography (silica gel, 1% ethyl acetate/methylene chloride) to, afford 1.76 g (70%) of a mixture of the E and Z isomers as a white solid: mp 132.0-134° C.; 1H NMR (CDCl3) δ 7.70-7.39 (m, 18 H), 7.10-6.80 (m, 6 H), 5.69 (s, 1 H), 5.68 (s, 1 H), 3.95 (s, 6 H), 3.93 (s, 3 H), 3.89 (s, 3 H), 3.85 (s, 3 H); 13C NMR (CDCl3) δ 162.2, 151.1, 148.8, 148.6, 143.0, 142.6, 140.0, 137.9, 135.9, 131.4, 130.1, 129.3, 129.1, 128.8, 128.8, 127.9, 127.1, 127.0, 126.0, 126.9, 123.1, 122.2, 118.3, 118.2, 112.6, 111.1, 110.7, 93.2, 92.9, 56.0, 55.9, 55.8; Anal. Calcd for C23H19NO2. Theoretical: C, 80.92; H, 5.61; N, 4.10. Found: C, 80.55; H, 5.80; N, 3.95.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US06479554B2
出典データセットuspto-grants-2002_11
ORD IDord-8bb94cd2c458429480bd688b8614e6b4
出典メモuspto-grants-2002_11