A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (<i>S</i>)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

Bleicher, Leo S.; Cosford, Nicholas D. P.; Herbaut, A.; McCallum, and J. Stuart; McDonald, Ian A.

doi:10.1021/jo971572d

Cited by 87 publications

(29 citation statements)

References 33 publications

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“…Chemicals: Pyrrolines 1a-f were synthesized following the protocol of Bleicher et al [40] adapted to the reaction path proposed by Jacob. [41] They were sublimed over P 2 O 5 and their purities checked by NMR and IR spectroscopy.…”

Section: Experimental and Computational Detailsmentioning

confidence: 99%

Hydrogen‐Bond Accepting Strength of Five‐Membered N‐Heterocycles:The Case of Substituted Phenylpyrrolines and Myosmines

et al. 2009

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The hydrogen‐bond (HB)accepting strengths of a series of five‐membered N‐heterocycles have been measured in CCl4 solution and/or calculated by theoretical methods. These molecules present a great chemical versatility, ranging from very weak π bases up to strongly HB acceptors, imines and amines. Among these compounds, special attention has been paid to myosmines, which are bifunctional molecules containing two very similar pyridinic and pyrrolinic sp2 nitrogen atoms. Infrared measurements provided the global HB basicities of these molecules, but the individual accepting strength of each nitrogen atom could not be achieved experimentally and had to be determined by theoretical calculations. Owing to their flexibility, the geometries of their different isomers were optimized and their basicities weighted by the calculated relative populations. To accurately estimate the individual HB strength of a nitrogen site, it was necessary to take into account a specific halogen bond between the second nitrogen atom and a solvent molecule. 1‐Pyrroline is a significantly stronger base than pyridine, but irrespective of the substituent on the pyridine ring, the pyrrolinic site is always the weakest HB acceptor in the myosmine molecules.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Experimental and Computational Detailsmentioning

confidence: 99%

Hydrogen‐Bond Accepting Strength of Five‐Membered N‐Heterocycles:The Case of Substituted Phenylpyrrolines and Myosmines

et al. 2009

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“…Using literature reported methods, 9 very low yields of the expected product resulted (20-30%) along with a complex mixture of uncharacterised byproducts. Nevertheless, a noticeable improvement was made by modifying the coupling procedure, 10 (Pd/C, PPh 3 , CuI, DME/H 2 O, D) where 10 was isolated in 52% yield. Finally, smooth alkaline hydrolysis of the ester with lithium hydroxide in aqueous THF provided 4 in high yield.…”

Section: Methodsmentioning

confidence: 98%

New Palladium-Catalysed Access to 3-(1'-Indanylidene) Phthalide, Precursor of the Core of Fredericamycin A

Bouyssi¹,

Balme²

2001

Synlett

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“…Hence, several synthetic routes combine the release of the terminal acetylene with a further transformation, without the isolation of the intermediate (Li et al, 2015). It was in the context of such considerations that the title acetylene compound, (I), previously reported (Bleicher et al, 1998), was isolated and crystallized. Herein, the crystal and molecular structures of (I) are described along with a detailed analysis of the molecular packing by Hirshfeld surface analysis, noncovalent interaction plots and computational chemistry.…”

Section: Chemical Contextmentioning

confidence: 99%

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

Caracelli¹,

Zukerman-Schpector²,

Schwab³

et al. 2019

Acta Cryst E

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The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the molecular packing is the formation, via hydroxy-O—H...O(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry \overline{3}. The aggregates are sustained by 12-membered {...OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—H...O(nitro) interactions, involving both nitro-O atoms. The aforementioned interactions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hydroxy-O—H...O(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts.

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A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

Cited by 87 publications

References 33 publications

Hydrogen‐Bond Accepting Strength of Five‐Membered N‐Heterocycles:The Case of Substituted Phenylpyrrolines and Myosmines

Hydrogen‐Bond Accepting Strength of Five‐Membered N‐Heterocycles:The Case of Substituted Phenylpyrrolines and Myosmines

New Palladium-Catalysed Access to 3-(1'-Indanylidene) Phthalide, Precursor of the Core of Fredericamycin A

2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

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