Cyclohexene → 2,2,5,5-Tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene

HRID 3040

反応式

HRID 3040 の反応式
[CH3:1][C:2]([CH3:28])([C:4]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)=[C:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:3].C1CCCCC=1>C1COCC1.[Pd]>[CH3:8][C:6]([CH3:9])([C:5]([C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)=[C:4]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[C:2]([CH3:1])([CH3:3])[CH3:28])[CH3:7]

参加物

5

反応物 2

HCID 8079CyclohexeneHCID 541103122,2,5,5-Tetramethyl-3,4-di(4-nitrophenyl)hex-3-ene

生成物 1

HCID 539135252,2,5,5-Tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene収率 50%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 0.62 g 2,2,5,5-tetramethyl-3,4-di(4-nitrophenyl)hex-3-ene,2.6 g cyclohexene and 1.4 g 10% Pd/C in THF was refluxed for 2 hrs. The Pd/C was removed by filtration and the residue after evaporation of the solvent was purified by chromatography on silica gel (25% CH2Cl2 -hexane) to give 0.285 g (50%) 2,2,5,5-tetramethyl-3-(4-nitrophenyl)-4-(4-aminophenyl)hex-3-ene: 1H NMR (CDCl3): δ0.66 (s, 8H), 0.70 (s, 8H), 3.61 (s, 2H), 6.61-6.63 (d, 2H), 7.30-7.34 (d, 2H), 8.12-8.14 (d, 2H): 13C NMR (CDCl3): δ32.81, 32.84, 37.59, 38.16, 113.58, 121.93, 131.34, 131.48, 133.12, 143.78, 144.58, 146.22, 146.88, 152.11.

後処理

  1. customThe Pd/C was removed by filtration
  2. customthe residue after evaporation of the solvent
  3. customwas purified by chromatography on silica gel (25% CH2Cl2 -hexane)

出典と根拠

ORDレコード
ord-db7374af57ba4dcaba7944b782005f33
出典データセット
uspto-grants-1998_03
特許番号
US05731890

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