Structure of quinidine, C20H24N2O2

Kashino, S.; Haisa, M.

doi:10.1107/s0108270183004515

Cited by 28 publications

(36 citation statements)

References 2 publications

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“…The bond lengths and angles in the quinoline part of the molecule are in good agreement with corresponding values in other alkaloids containing the methoxyquinoline ring such as derivatives of quinine and quinidine (Suszko-Purzycka et al, 1985;Suszko-Purzycka et al, 1987;Dupont et al, 1985), and quinidine base (Kashino & Haisa, 1983). The only exception is the C(26)-C(27) bond length of 1.356 (4) A, which is somewhat short when compared with the average value of 1.410 (6) rings in the crystal.…”

Section: Meosupporting

confidence: 81%

“…The bond lengths and angles in the bicyclic quinuclidine part of the molecule agree well with those observed in other Cinchona alkaloids such as derivatives of quinine and quinidine (Suszko-Purzycka et al, 1985;Suszko-Purzycka, Lipifiska, Karczmarzyk & Pniewska, 1987;Dupont et al, 1985), quinidine (Kashino & Haisa, 1983), cinchonidine (Oleksyn, 1982) and cinchonine (Oleksyn et al, 1979). However, the asymmetry of the N(1) -C(8) (41) 0.8022 (6) 0.500 0.500 11.4 (2) C (42) 0.7300 (5) 0.5122 (2) 0.5459 (2) 11.7 (1) C (43) 0.6025 (4) 0.5115 (2) 0.5447 (1) 7.9 (1) C (44) 0.5399 (5) 0.500 0.500 7.0 (1) C (45) 0.3935 (7) 0.500 0.500 14.1 (3) C (6) …”

Section: Meosupporting

confidence: 80%

“…quinidine (Kashino & Haisa, 1983), cinchonidine (Oleksyn, 1982) and cinchonine (Oleksyn, Lebioda & Ciechanowicz-Rutkowska, 1979), it was impossible to obtain quinine in pure form by simple recrystallization of the commercial product. Commercial preparations of quinine, obtained from cinchona bark, contain small amounts of other alkaloids, among them dihydroquinine (Henry, 1949;Suszko-Purzycka & Trzebny, 1964, 1965.…”

mentioning

confidence: 99%

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Structure of quinine monohydrate toluene solvate

Pniewska¹,

Suszko-Purzycka²

1989

Acta Crystallogr C

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Section: Meosupporting

confidence: 81%

Section: Meosupporting

confidence: 80%

mentioning

confidence: 99%

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Structure of quinine monohydrate toluene solvate

Pniewska¹,

Suszko-Purzycka²

1989

Acta Crystallogr C

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“…In the solid state the molecules of compound 1 are connected to helical chains by hydrogen bonds in a similar manner as found in compound 2 (see the figure in [8]) and in quinidine [2]. The chain direction in 1 is [100] and corresponds to the [010] direction in 2.…”

Section: Discussionmentioning

confidence: 83%

“…The title compound 1 is derived from quinidine [2] via quincoridine® (QCD) [1,3,4] and is to be compared to the (lS,2S,4S,5S)-diastereomer 2 which is derived from quinine [5] via quincorine® (QCI) [1,3,4], The transformation of QCD and QCI to compounds 1 and 2, respectively, can formally be described as the replacement of the vinyl group by the ethynyl group (see scheme 1 in [6]). Compound 1 is called 10,11-didehydroquincoridine and compound 2 10,11-didehydro-quincorine [6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (1S,2R,4S,5S)-5-ethynyl-2-hydroxymethyl-1-azabicyclo[2.2.2]octane, (HC2)(HOCH2)C7H11N)

Wartchow¹,

Frackenpohl²,

Hoffmann³

2001

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialQuincoridine® [1] (2.0 g, 12 mmol) was dissolved in dry CCI4 (15 ml). Bromine (1.1 ml, 21.5 mmol) was added at 273 Κ. The reaction mixture was stirred for lh. After removal of the solvent in vacuo the resulting yellow solid was dissolved in CHCI3 (25 ml). Et3N (3.1 ml, 24 mmol) was added and the mixture was then stirred for 4h at RT. After work-up (CHCI3 and saturated aqueous solution NaHC03) the vinylic bromide (0.2 g, 0.81 mmol) was dissolved in THF (10 ml), followed by addition of powdered KOH (116 mg, 2.0 mmol) and aliquat 336® (0.73 ml, 0.16 mmol). The reaction mixture was heated at reflux for 7 h. Work-up (CHCI3 and saturated aqueous solution NaHCOs) and column chromatography (ethyl acetate / methanol 6:1) furnished the title compound which crystallized after 5 h at 273 K. The compound melts at 317 Κ and sublimes readily. DiscussionThe title compound 1 is derived from quinidine [2] via quincoridine® (QCD) [1,3,4] and is to be compared to the (lS,2S,4S,5S)-diastereomer 2 which is derived from quinine [5] via quincorine® (QCI) [1,3,4], The transformation of QCD and QCI to compounds 1 and 2, respectively, can formally be described as the replacement of the vinyl group by the ethynyl group (see scheme 1 in [6]). Compound 1 is called 10,11-didehydroquincoridine and compound 2 10,11-didehydro-quincorine [6]. In view of the high synthetic flexibility of alkynes we expect that 1 and 2 will become valuable homochiral building blocks, e.g. in asymmetric synthesis and in medicinal chemistry, similar to QCD and QCI [3,4,7]. The terminal alkynes 1 and 2 have the advantage of being solids at room temperature, while QCD and QCI are liquids. The crystal structure of 2 has already been reported inThe X-ray analysis of 1 (this work) shows that its crystal packing has the higher point group symmetry (222 instead of 2) but the lower density by about 2 %. In the solid state the molecules of compound 1 are connected to helical chains by hydrogen bonds in a similar manner as found in compound 2 (see the figure in [8]) and in quinidine [2]. The chain direction in 1 is [100] and corresponds to the [010] direction in 2. Substituted quinuclidines are often twisted [9]. The dihedral angles C2-N1-C4-C3, C6-N1-C4-C5 and C7-N1-C4-C8 are 10.9°, 9.7° and 9.1°, respectively, with an average of 9.9° for molecule 1 and 3.7°, 6.7°

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Crystal Structure of Quinine: The Effects of Vinyl and Methoxy Groups on Molecular Assemblies of Cinchona Alkaloids Cannot Be Ignored

Hisaki

Hiraishi

Sasaki

et al. 2012

Chemistry An Asian Journal

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Quinine, one of Cinchona alkaloids, has been of great interest from medical, synthetic, and supramolecular viewpoints. However, unaccountably, the guest-free (GF) crystal of quinine containing no solvent or other molecules has not been reported for nearly three decades, although GF crystals of other Cinchona alkaloids, such as quinidine, cinchonidine, and cinchonine, are already known. In this study, we successfully revealed the crystal structure of quinine, which belongs to the P2(1) space group with the cell parameters of a=6.0587(1), b=19.2492(5), c=22.2824(7) Å, β=92.1646(11)°, and V=2596.83(12) Å(3). Interestingly, the crystal has three crystallographically independent molecules in the cell (Z'=3) that are connected through a N(quinoline)⋅⋅⋅H-O hydrogen bond to form a pseudo three-two-fold (3(2)) double-helical motif. The helical motif is completely different from those observed in GF crystals of other Cinchona alkaloids. Hierarchical comparison on the crystal structures of a series of Cinchona alkaloids including quinine clearly demonstrated that only small structural differences of a molecule, particularly the position of the vinyl group, cause a significant variety of assembly manner in the crystalline state. There have been no reports systematically demonstrating such steric effect in crystals of Cinchona alkaloids, and, therefore, the present system contributes to the design of desired functional crystal structures.

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Structure of quinidine, C20H24N2O2

Abstract: M r--324.43, monoclinic, P2., a= 11.883 (2), b= 7.037 (4), c= 11.256 (2)~, fl= 111.95(1) ° , V= 873.1(5) A 3, Z=2, D =1.23,

Cited by 28 publications

References 2 publications

Structure of quinine monohydrate toluene solvate

Structure of quinine monohydrate toluene solvate

Crystal structure of (1S,2R,4S,5S)-5-ethynyl-2-hydroxymethyl-1-azabicyclo[2.2.2]octane, (HC2)(HOCH2)C7H11N)

Crystal Structure of Quinine: The Effects of Vinyl and Methoxy Groups on Molecular Assemblies of Cinchona Alkaloids Cannot Be Ignored

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