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3-Dimethylallyl-4-dimethylallyloxyquinolin-2-one

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Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum bucharicum

C19H23NO2: 297.1729

Mp: 113–114°C (Me2CO) [1]

Solubility: very sol. CHCl3 [1]

UV: 227, 272, 282, 313, 324, 338 (4.10, 3.50, 3.41, 3.35, 3.46, 3.35) [1]

IR: 3300, 1650 [1]

MSm/z: 297(M+, 6), 229(25), 228(100), 214(18), 212(27), 200(16), 186(26), 174(24), 69(36) [1]

1H NMR: 1.61, 1.75, 1.82(6H, 3H, 3H, each s, 4 × CH3), 3.37, 4.44(each 2H, d, J = 7.5, CH2), 5.25, 5.51(each 1H, t, J = 7.5, =CH), 7.08–7.45(3H, m, H–Ar), 7.65(1H, dd, J = 8.5, 2, H-5) [1]

13 C NMR: [ 2]

Table 1

C-2

161.2

C-8

115.9

C-1″

23.8

 3

117.7

 8a

139.0

 2″

121.7

 4

165.8

 1′

71.2

 3″

132.5

 4a

122.8

 2′

119.7

3″-CH3

18.0

 5

123.1

 3′

137.4

3″-CH3

25.8

 6

122.1

3′-CH3

18.1

   

 7

129.8

3′-CH3

25.9

   

References

  1. 1.
    E.F. Nesmelova, I.A. Bessonova, S.Yu. Yunusov, Chem. Nat. Comp. 18, 507 (1982)Google Scholar
  2. 2.
    G.M. Sheriha, K. Abouamer, B.Z. Elshtaiwi, A.S. Ashour, F.A. Abed, H.H. Alhallaq, Phytochemistry 26, 3339 (1987)Google Scholar

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