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Haplophyllidine

Reference work entry

CAS Registry Number: 18063-21-3 Open image in new window

Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids

Biological sources: Haplophyllum perforatum

C18H23NO4: 317.1627

Mp: 110–111°C (pet. ether), 148°C (O–Ac), 136°C (tetrahydro) [1]

[α]D −16° (Me2CO) [1]

Solubility: very sol. MeOH, EtOH, Me2CO, C6H6, CHCl3, EtOAc [1]

UV: 258 (4.18) [2]

IR: 3300, 3142, 3115, 1612, 1252 [1, 2]

MSm/z: 317(M+, 4), 302(2), 287(14), 285(22), 270(72), 248(68), 216(100), 188(94), 173(12), 69(6) [3]

1H NMR(CCl4): 1.67, 1.73(each 3H, s, 2 × CH3), 3.05, 4.21(each 3H, s, 2 × OCH3), 4.00(1H, m, O–CH–), 5.25(1H, t, J = 7, =CH), 6.86, 7.48(each 1H, J = 3, H-3, H-2) [3]

13 C NMR: [ 4]

Table 1

C-2

142.0

C-5

18.4

C-10

119.5

 2a

161.5

 6

23.9

 11

133.2

 3

104.3

 7

69.4

 12

25.8

 3a

116.8

 8

78.8

 13

17.8

 4

157.9

 8a

150.1

4-OCH3

58.1

 4a

104.7

 9

29.7

8-OCH3

50.3

References

  1. 1.
    T. Shakirov, G.P. Sidyakin, S.Yu. Yunusov, DAN UzSSR (6), 28 (1959); No. 9, 40 (1960)Google Scholar
  2. 2.
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  3. 3.
    I.A. Bessonova, Z.Sh. Faizutdinova, Ya.V. Rashkes, M.R. Yagudaev, S.Yu. Yunusov, Chem. Nat. Comp. 5, 231 (1969); R. Shakirov, M.V. Telezhenetskaya, I.A. Bessonova, S.F. Aripova, I.A. Israilov, M.N. Sultankhodzhaev, V.I. Vinogradova, V.I. Akhmedzhanova, T.S. Tulyaganov, B.T. Salimov, V.A. Tel’nov, Chem. Nat. Comp. 32, 932 (1996)Google Scholar
  4. 4.
    M.R. Yagudaev, I.A. Bessonova, Chem. Nat. Comp. 25, 20 (1989)Google Scholar
  5. 5.
    F.S. Sadritdinov, A.G. Kurmukov, The Pharmacology of the Plant Alkaloids and Their Use in Medicine [in Russian] (UzSSR, Tashkent, 1980), p. 275Google Scholar
  6. 6.
    S.S. Nazrullaev, I.A. Bessonova, Kh.S. Akhmedkhodjaeva, Chem. Nat. Comp. 37, 551 (2001)Google Scholar

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