200,000+ products from a single source!

sales@angenechem.com

Home > Other Building Blocks > 492-08-0

492-08-0

492-08-0 | (+)-Sparteine

CAS No: 492-08-0 Catalog No: AG003BDC MDL No:MFCD00869353

Product Description

Catalog Number:
AG003BDC
Chemical Name:
(+)-Sparteine
CAS Number:
492-08-0
Molecular Formula:
C15H26N2
Molecular Weight:
234.3803
MDL Number:
MFCD00869353
IUPAC Name:
(1R,2S,9R,10R)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
InChI:
InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m1/s1
InChI Key:
SLRCCWJSBJZJBV-TUVASFSCSA-N
SMILES:
C1CC[C@@H]2N(C1)C[C@H]1C[C@@H]2CN2[C@@H]1CCCC2
EC Number:
201-988-8

Properties

Complexity:
263  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
234.21g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
234.387g/mol
Monoisotopic Mass:
234.21g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
6.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5  

Literature

Title Journal
Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline. Bioorganic & medicinal chemistry 20121001
Asymmetric synthesis of trans-2,3-disubstituted indoline derivatives. The Journal of organic chemistry 20120106
[Derivatives of lupinin and epilupinin as ligands of various cholinesterases]. Zhurnal evoliutsionnoi biokhimii i fiziologii 20120101
[Isomeric derivatives of lupinine and epilupinine--organophosphorus inhibitors of cholinesterases]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20120101
[Reversible lupininin inhibitors of cholinesterases of mammalian blood and of optical ganglia of individuals of the commander squid Berryteuthis magister from different zones of species areal]. Zhurnal evoliutsionnoi biokhimii i fiziologii 20120101
Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications. The Journal of organic chemistry 20110805
Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions. Organic letters 20110805
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry 20110714
Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization. The Journal of organic chemistry 20110415
Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition. The Journal of organic chemistry 20110107
Development and application of a method to investigate drug-metabolizing enzyme inhibitors using sparteine for probe of cytochrome P450 2D6 and tris(2,2'-bipyridine)ruthenium(II)-electrogenerated chemiluminescence detection. Chemical & pharmaceutical bulletin 20110101
Experimental and computational study of a direct O2-coupled Wacker oxidation: water dependence in the absence of Cu salts. Journal of the American Chemical Society 20100901
Can the genotype or phenotype of two polymorphic drug metabolising cytochrome P450-enzymes identify oral lichenoid drug eruptions? Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology 20100701
Characterization of a rhodium-sparteine complex, [((-)-sparteine)Rh(eta4-COD)]+: crystal structure and DNMR/DFT studies on ligand-rotation dynamics. Dalton transactions (Cambridge, England : 2003) 20100321
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation. Organic letters 20100205
Asymmetric catalysis of homo-coupling of 3-substituted naphthylamine and hetero-coupling with 3-substituted naphthol leading to 3,3'-dimethyl-2,2'-diaminobinaphthyl and -2-amino-2'-hydroxybinaphthyl. Chirality 20100201
Estimation of the interindividual variability of cytochrome 2D6 activity from urinary metabolic ratios in the literature. Drug metabolism and pharmacokinetics 20100101
Reactions of (-)-sparteine with alkali metal HMDS complexes: conventional meets the unconventional. Chemical communications (Cambridge, England) 20091021
Optically active (aR)- and (aS)-linear and vaulted biaryl ligands: deracemization versus oxidative dimerization. Journal of the American Chemical Society 20091014
Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine. Journal of the American Chemical Society 20090527
Epiquinamide: a poison that wasn't from a frog that was. Journal of natural products 20090227
Total synthesis of (+/-)-alpha-isosparteine, (+/-)-beta-isosparteine, and (+/-)-sparteine from a common tetraoxobispidine intermediate. The Journal of organic chemistry 20081017
A new catalytic Cu(II)/sparteine oxidant system for beta,beta-phenolic couplings of styrenyl phenols: synthesis of carpanone and unnatural analogs. Organic letters 20080918
A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine. Organic letters 20080619
A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine. Organic letters 20080403
Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis. Chemical communications (Cambridge, England) 20080214
Asymmetric lithiation-substitution of amines involving rearrangement of borates. Organic letters 20080103
Cholinesterase hydrolysis of substituted lupinine benzoates. Doklady. Biochemistry and biophysics 20080101
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev. Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101
Stereocontrolled synthesis and alkylation of cyclic beta-amino esters: asymmetric synthesis of a (-)-sparteine surrogate. Organic & biomolecular chemistry 20071121
A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties. The Journal of organic chemistry 20070803
A natural variant of the heme-binding signature (R441C) resulting in complete loss of function of CYP2D6. Drug metabolism and disposition: the biological fate of chemicals 20070801
Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats. European journal of pharmacology 20070622
[Phenotypes of oxidation and acetylation in Alzheimer's disease--preliminary report]. Psychiatria polska 20070101
Enantioselective nitroaldol (Henry) reaction using copper(II) complexes of (-)-sparteine. Chemical communications (Cambridge, England) 20061021
Neuronal damage and changes in the expression of muscarinic acetylcholine receptor subtypes in the neonatal rat cerebral cortical upon exposure to sparteine, a quinolizidine alkaloid. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20061001
Pd(II)-catalyzed conversion of styrene derivatives to acetals: impact of (-)-sparteine on regioselectivity. Organic letters 20060316
Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation. Journal of the American Chemical Society 20060315
Asymmetric synthesis of 4,5,6- and 3,4,5,6-substituted azepanes by a highly diastereoselective and enantioselective lithiation-conjugate addition sequence. Journal of the American Chemical Society 20060222
[Clinical significance of oxidation and acetylation genetic polymorphism in patients with hyperthyreosis]. Endokrynologia Polska 20060101
Origin of enantioselection in chiral alcohol oxidation catalyzed by Pd[(-)-sparteine]Cl2. Journal of the American Chemical Society 20051026
A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core. Organic letters 20051013
Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate. Organic letters 20050929
Enantioselective lithiation of O-alkyl and O-alk-2-enyl Carbamates in the presence of (-)-sparteine and (-)-alpha-isosparteine. A theoretical study. The Journal of organic chemistry 20050527
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine. Organic letters 20050512
A synthesis of (+/-)-sparteine. Organic & biomolecular chemistry 20050421
Absolute configuration of 2-(tributylstannyl)pyrrolidine by anomalous dispersion X-ray analysis. The Journal of organic chemistry 20050107
[Synthesis of lupinine derivatives of flavonoids]. Bioorganicheskaia khimiia 20050101
Is the A-ring of sparteine essential for high enantioselectivity in the asymmetric lithiation-substitution of N-Boc-pyrrolidine? Journal of the American Chemical Society 20041201
An experimental and computational study of the enantioselective lithiation of N-Boc-pyrrolidine using sparteine-like chiral diamines. Journal of the American Chemical Society 20041201
Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves. American journal of veterinary research 20041101
Total synthesis of (-)-alpha-kainic acid by (-)-sparteine-mediated asymmetric deprotonation-cycloalkylation. Organic letters 20041014
Effect of ligand structure on the asymmetric cyclization of achiral olefinic organolithiums. The Journal of organic chemistry 20040903
Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction. Organic letters 20040902
Concise asymmetric synthesis of (-)-sparteine. Chemical communications (Cambridge, England) 20040821
Evaluation of (+)-sparteine-like diamines for asymmetric synthesis. The Journal of organic chemistry 20040820
A short synthesis of (+/-)-cytisine. Organic & biomolecular chemistry 20040707
Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives. Chemistry (Weinheim an der Bergstrasse, Germany) 20040705
A computational model relating structure and reactivity in enantioselective oxidations of secondary alcohols by (-)-sparteine-Pd(II) complexes. Journal of the American Chemical Society 20040630
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin]. Zhurnal evoliutsionnoi biokhimii i fiziologii 20040101
Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base. The Journal of organic chemistry 20030919
Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine. Journal of the American Chemical Society 20030611
Scope of enantioselective palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine. The Journal of organic chemistry 20030530
Synthetic applications of lithiated N-Boc allylic amines as asymmetric homoenolate equivalents. The Journal of organic chemistry 20030221
Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities. Journal of medicinal chemistry 20030102
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors. Doklady. Biochemistry and biophysics 20030101
A readily-accessible (+)-sparteine surrogate. Journal of the American Chemical Society 20021009
Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation-substitution sequences: synthetic development and mechanistic pathway. The Journal of organic chemistry 20020920
Control of the conformational equilibria in aza-cis-decalins: structural modification, solvation, and metal chelation. The Journal of organic chemistry 20020906
First asymmetric total synthesis of (+)-sparteine. Organic letters 20020725
Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes. Organic letters 20020627
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis. Phytochemistry 20020601
Lobocyclamide B from Lyngbya confervoides. Configuration and asymmetric synthesis of beta-hydroxy-alpha-amino acids by (-)-sparteine-mediated aldol addition. Organic letters 20020530
Conformational control of flexible molecules: design and synthesis of novel chiral 1,5-diaza-cis-decalins. The Journal of organic chemistry 20020503
Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract. Journal of agricultural and food chemistry 20020410
Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans. Clinical pharmacology and therapeutics 20020401
An experimental and computational investigation of the enantioselective deprotonation of Boc-piperidine. Journal of the American Chemical Society 20020306
Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men. Clinical pharmacology and therapeutics 20020301
Pharmacokinetics of therapeutic doses of tropisetron in healthy volunteers. British journal of clinical pharmacology 20011201
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers. Pharmacology & toxicology 20011201
Inhibition of cytochrome P4502D6 activity with paroxetine normalizes the ultrarapid metabolizer phenotype as measured by nortriptyline pharmacokinetics and the debrisoquin test. Clinical pharmacology and therapeutics 20011001
Indolizidine and quinolizidine alkaloids. Natural product reports 20011001
Chiral diamines 4: a computational study of the enantioselective deprotonation of Boc-pyrrolidine with an alkyllithium in the presence of a chiral diamine. Journal of the American Chemical Society 20010829
Absorption and disposition of levocetirizine, the eutomer of cetirizine, administered alone or as cetirizine to healthy volunteers. Fundamental & clinical pharmacology 20010801
Influence of CYP2D6 genotype and medication on the sparteine metabolic ratio of psychiatric patients. European journal of clinical pharmacology 20010701
Kinetics and mechanism of the (-)-sparteine-mediated deprotonation of (E)-N-Boc-N-(p-methoxyphenyl)-3-cyclohexylallylamine. Journal of the American Chemical Society 20010530
Novel sparteine-mediated enantio-dichotomic formal synthesis of R-(-)- and S-(+)-curcuphenol. The Journal of organic chemistry 20010420
Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates. Organic letters 20010419
Moving toward genetic profiling in patient care: the scope and rationale of pharmacogenetic/ecogenetic investigation. Drug metabolism and disposition: the biological fate of chemicals 20010401
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine. Farmaco (Societa chimica italiana : 1989) 20010301
Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones. The Journal of organic chemistry 20010209
Immunolocalization of alkaloids and X-ray microanalysis of elements in lupin seeds. Protoplasma 20010101
Drug metabolism and genetic polymorphism in subjects with previous halothane hepatitis. Scandinavian journal of gastroenterology 19930801
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products 19910101
Severe complications of antianginal drug therapy in a patient identified as a poor metabolizer of metoprolol, propafenone, diltiazem, and sparteine. Klinische Wochenschrift 19871215
Screening for new compounds with antiherpes activity. Antiviral research 19841001
Antifibrillatory, cardiovascular and toxic effects of sparteine, butylsparteine and pentylsparteine. Arzneimittel-Forschung 19800101
[Effect of sparteine sulfate on the predamaged conduction system of the heart]. Zeitschrift fur Kardiologie 19750501

© 2019 Angene International Limited. All rights Reserved.