“…These angles are 13.6(4) and 15.0(5) ° for leucoxine.HBr (average 14.3°); and 21.2(8) and 20.5 (1.0) ° for isoboldine.HBr (average 20.9°). These twist angles are to be compared with an angle of 29.9 ° reported by Shamma & Slusarchyk (1964) from Ashida, Pepinsky & Okaya's (1963)determination of the structure of bulbocapnine methiodide. The three different angles (14.3, 20-9 and 29.9 ° ) can be rationalized on the basis of the differences in the substituents on the aporphine nucleus in the three cases.…”
Section: S Etc)mentioning
confidence: 94%
“…Isoboldine (CI9H2104N , formula II) is an aporphine alkaloid of known chemical structure (for references see Shamma & Slusarchyk, 1964;and Shamma, 1967). The absolute configuration indicated in (II) is implied by the optical rotatory dispersion data (Craig & Roy, 1965) on boldine, which differs in structure from isoboldine only by the interchange of the OCH 3 and OH groups at the upper left of (II).…”
The X-ray crystal-structure analysis of leucoxine (I) hydrobromide (C20H21OsN.HBr) completes the elucidation of the molecular structure of this alkaloid and establishes its absolute configuration as that of the S series of aporphines. The structure analysis of isoboldine (II) hydrobromide (Cj9H2104N .HBr) furnishes details of its molecular structure and confirms the absolute configuration (also S series) implied from the configurational assignment made previously for its isomer isoboldine from an optical rotatory dispersion study. The twist from coplanarity about the central bond of the biphenyl moiety is ~14 ° in (I).HBr and ~21 o in (II).HBr (cf. ~30 ° in the N-methylbulbocapninium ion). The different twists result from the different substituents on the basic aporphine ring system. Both hydrobromides are orthorhombic (P2~2~21) with Z = 4.
“…These angles are 13.6(4) and 15.0(5) ° for leucoxine.HBr (average 14.3°); and 21.2(8) and 20.5 (1.0) ° for isoboldine.HBr (average 20.9°). These twist angles are to be compared with an angle of 29.9 ° reported by Shamma & Slusarchyk (1964) from Ashida, Pepinsky & Okaya's (1963)determination of the structure of bulbocapnine methiodide. The three different angles (14.3, 20-9 and 29.9 ° ) can be rationalized on the basis of the differences in the substituents on the aporphine nucleus in the three cases.…”
Section: S Etc)mentioning
confidence: 94%
“…Isoboldine (CI9H2104N , formula II) is an aporphine alkaloid of known chemical structure (for references see Shamma & Slusarchyk, 1964;and Shamma, 1967). The absolute configuration indicated in (II) is implied by the optical rotatory dispersion data (Craig & Roy, 1965) on boldine, which differs in structure from isoboldine only by the interchange of the OCH 3 and OH groups at the upper left of (II).…”
The X-ray crystal-structure analysis of leucoxine (I) hydrobromide (C20H21OsN.HBr) completes the elucidation of the molecular structure of this alkaloid and establishes its absolute configuration as that of the S series of aporphines. The structure analysis of isoboldine (II) hydrobromide (Cj9H2104N .HBr) furnishes details of its molecular structure and confirms the absolute configuration (also S series) implied from the configurational assignment made previously for its isomer isoboldine from an optical rotatory dispersion study. The twist from coplanarity about the central bond of the biphenyl moiety is ~14 ° in (I).HBr and ~21 o in (II).HBr (cf. ~30 ° in the N-methylbulbocapninium ion). The different twists result from the different substituents on the basic aporphine ring system. Both hydrobromides are orthorhombic (P2~2~21) with Z = 4.
“…X-ray crystallographic studies (17) indicate that the biphenyl portion of aporphine systems is appreciably strained, the angle of twist being 29.9". This strain increases in aporphines bearing substituents at Positions 1 and/or 11.…”
“…C 68,13 H 6,89 K 5,54o/b 6. 2,3,7,8,9, HCZ). In 300 g wie untcr 5 angcgebcn bereitctc Polyphosphorsaure tragt man unter Ruhren bei 165" 31,6 g (0,l mol) 9-Hydrochlorid ein, halt 20 Min.…”
Summary. Synthesis and cardiovascular evaluation of ketones 10, 11 and 12 and of their derivatives 14 to 35 are described.Die Aporphin-Alkaloide D-(-)-Nuciferin ( l ) , D-(-)-1-Hydroxy-2-methoxy-apor- Nachstehend berichten wir iiber die Synthese der Ketone 10, 11, 12 und einiger ihrer Derivate rnit gleichem Kohlenstoffskelett sowie iiber die wichtigsten pharmakologischen Untersuchungen dieser Verbindungen.
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