|
| (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol Basic information |
Product Name: | (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol | Synonyms: | (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol;(1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1β-ol;Retamine;7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol, dodecahydro-, (1S,7R,7aS,14R,14aS)- | CAS: | 2122-29-4 | MF: | C15H26N2O | MW: | 250.38 | EINECS: | | Product Categories: | | Mol File: | 2122-29-4.mol | |
| (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol Chemical Properties |
Melting point | 165-166° | alpha | D20 +46.2° (c = 1.017 in abs ethanol) |
| (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol Usage And Synthesis |
Description | This sparteine alkaloid was first isolated by Battandier and Malosse from Retama
sphaerocarpa Boiss. and found to give colour reactions suggesting a relationship
with sparteine. It has [α]20D + 46.2° (c 1.017, EtOH) and yields crystalline salts
and derivatives including the hydrochloride, m.p. 272-3°C; picrate, m.p. 165-
6°C; phenylurethane, m.p. 190-1 °c and the acetyl derivative as hygroscopic
crystals, m.p. about 60°C. The earlier structure as 8-hydroxysparteine has been
shown to be wrong, the correct structure, established by synthesis, being 12-{3-
hydroxysparteine. | References | Battandier, Malosse., Compt. rend., 125, 360,450 (1897)
Ribas, Sanchez, Primo., Anales, [is. y. quim., 42, 516 (1946)
Ribas, Fraga., Anales. Real. Soc. Espan [is. y. QUim., 45B, 1426 (1949)
Ribas, Fraga., ibid, 46B, 665 (1950)
Fragaetal., Tetrahedron, 11,78 (1960)
Revised structure:
Bohlmann et al., Chem. Ber., 98, 653, 659 (1965)
Ribas, Castedo, Garcfa., Tetrahedron Lett., 3181 (1965)
Shin, Fonzes, Marion., Can. 1. Chem., 43,2012 (1965) |
| (1S,7aβ,14aα)-Dodecahydro-7β,14β-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-1-ol Preparation Products And Raw materials |
|