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Perfamine

Reference work entry

CAS Registry Number: 59557-95-8 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum acutifolium, H. perforatum

C18H19NO4: 313.1314

Mp: 164–165°C (Et2O–Me2CO) [1], 212°C (semicarbazone) [2], 225°C (hydrogenation product) [1, 3]

[α]D +53° (CHCl3) [1]

Solubility: very sol. CHCl3; sol. EtOH, MeOH, Me2CO, Et2O; insol. H2O [1]

UV: 215, 264, 272, 345 (4.30, 4.43, 4.43, 3.91) [1]

IR: 3145, 3115, 1670 [1]

MSm/z: 313(M+, 4), 298(2), 283(6), 266(14), 252(8), 245(100), 240(15), 230(18), 228(12), 227(92), 216(24) [1]

1H NMR: 1.28, 1.43(each 3H, s, 2 × CH3), 2.73, 4.76(2H, d; 1H, t, J = 6.5, H-9, H-10), 3.04, 4.37(each 3H, s, 2 × OCH3), 6.12, 8.03(each 1H, d, J = 10, H-6, H-5), 7.10, 7.66(each 1H, d, J = 3, H-3, H-2) [1]

13 C NMR: [ 4]

Table 1

C-2

143.5

C-5

137.2

C-10

113.6

 2a

162.1

 6

124.4

 11

136.2

 3

105.3

 7

201.4

 12

17.6

 3a

115.5

 8

86.3

 13

25.7

 4

158.0

 8a

157.6

4-OCH3

59.0

 4a

105.6

 9

42.3

8-OCH...

References

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    D.M. Razakova, I.A. Bessonova, S.Yu. Yunusov, (1976) Chem. Nat. Comp. 11, 828 (1975); 12, 709Google Scholar
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  3. 3.
    D.M. Razakova, I.A. Bessonova, S.Yu. Yunusov, Chem. Nat. Comp. 19, 245 (1983)Google Scholar
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    Z. Rosza, M. Rabik, K. Szendrei, A. Kalman, G. Argay, I. Pelczer, M. Aynechi, I. Mester, J. Reisch, Phytochemistry 25, 2005 (1986)Google Scholar
  5. 5.
    S.S. Nazrullaev, I.A. Bessonova, Kh.S. Akhmedkhodjaeva, Chem. Nat. Comp. 37, 551 (2001)Google Scholar

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