硝基甲烷-(15)N → HCID 131728910，化合物

反应方程式

[CH2:1]([C:4]1[CH2:5][C@@H:6]2[C@H:9]([CH:10]=1)[C:8](=[CH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH:2]=[CH2:3].N12CCCN=C1CCCCC2.P([O-])(O)(O)=O.[K+].[N+:36]([CH3:39])([O-:38])=[O:37]>>[CH2:1]([C:4]1[CH2:5][C@@H:6]2[C@H:9]([CH:10]=1)[C@@:8]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH2:39][N+:36]([O-:38])=[O:37])[CH2:7]2)[CH:2]=[CH2:3]

参与物

反应物 4

HCID 6375硝基甲烷-(15)N

HCID 81184DBU

HCID 516951磷酸钾

HCID 91368801HCID 91368801，化合物

产物 1

HCID 131728910HCID 131728910，化合物

反应条件

温度: 55 °C

实验过程

Tert-butyl(±)-(1S,5R)-3-allylbicyclo[3.2.0]hept-3-en-6-ylideneacetate (0.63 g, 2 mmol) was dissolved in nitromethane (5 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (0.45 mL, 3 mmol) was added, and the mixture was heated with stirring at 50 to 60° C. for 7 hours. The mixture was allowed to cool, and a saturated aqueous solution of potassium dihydrogen phosphate was then added thereto, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil substance (367.0 mg, 60%).