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485-70-1 | 9-epi-Cinchonine
CAS No: 485-70-1 Catalog No: AG003NKP MDL No:
Product Description
Catalog Number:
AG003NKP
Chemical Name:
9-epi-Cinchonine
CAS Number:
485-70-1
IUPAC Name:
(R)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
InChI:
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19+/m0/s1
InChI Key:
KMPWYEUPVWOPIM-YXUGBTPSSA-N
UNII:
35VE0JQR6N
NSC Number:
757801
Properties
Complexity:
412
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
294.173g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
294.398g/mol
Monoisotopic Mass:
294.173g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
36.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7
Literature
| Title | Journal |
|---|---|
| Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents. | Bioorganic & medicinal chemistry letters 20120901 |
| Organocatalytic asymmetric conjugate addition of 3-monosubstituted oxindoles to (E)-1,4-diaryl-2-buten-1,4-diones: a strategy for the indirect enantioselective furanylation and pyrrolylation of 3-alkyloxindoles. | Chemistry (Weinheim an der Bergstrasse, Germany) 20120521 |
| Desymmetrization of cyclohexadienones via asymmetric Michael reaction catalyzed by cinchonine-derived urea. | Organic letters 20111007 |
| Tosyl esters of cinchonidine and cinchonine alkaloids: the structure-reactivity relationship in the hydrolysis to 9-epibases. | Acta crystallographica. Section C, Crystal structure communications 20110901 |
| Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells. | Environmental toxicology 20110801 |
| Novel molecularly imprinted microsphere using a single chiral monomer and chirality-matching (S)-ketoprofen template. | Journal of chromatography. A 20110617 |
| Rapid and green analytical method for the determination of quinoline alkaloids from Cinchona succirubra based on Microwave-Integrated Extraction and Leaching (MIEL) prior to high performance liquid chromatography. | International journal of molecular sciences 20110101 |
| Enantioselective radical addition to ketimines: a synthetic route towards α,α-disubstituted α-amino acids. | Chemistry (Weinheim an der Bergstrasse, Germany) 20101122 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate. | Chirality 20100601 |
| Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. | Talanta 20100315 |
| Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine. | Magnetic resonance in chemistry : MRC 20100101 |
| Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. | Journal of the American Chemical Society 20081105 |
| Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis. | Journal of the American Chemical Society 20081001 |
| An improved synthesis of 10,11-didehydro Cinchona alkaloids. | Chirality 20080301 |
| Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication. | Journal of fluorescence 20080101 |
| Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids. | Chirality 20080101 |
| Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones. | Organic & biomolecular chemistry 20070307 |
| Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. | Chirality 20070201 |
| Asymmetric activation of tropos 2,2'-biphenol with cinchonine generates an effective catalyst for the asymmetric strecker reaction of N-tosyl-protected aldimines and ketoimines. | Angewandte Chemie (International ed. in English) 20070101 |
| Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative. | Chemical communications (Cambridge, England) 20060321 |
| Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry. | Journal of the American Society for Mass Spectrometry 20050201 |
| Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine. | Bioorganic chemistry 20040801 |
| Direct STM investigation of cinchona alkaloid adsorption on Cu(III). | Langmuir : the ACS journal of surfaces and colloids 20040413 |
| Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin. | Anti-cancer drugs 20030701 |
| Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone. | The Journal of organic chemistry 20030613 |
| Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20030101 |
| Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination. | Organic letters 20020905 |
| A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine. | The Analyst 20020101 |
| Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. | The Journal of pharmacy and pharmacology 20010701 |
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