(1R,2R)-(-)-2-benzyloxycyclopentyl isocyanate - CAS 737001-14-8
Category:
Main Product
Product Name:
(1R,2R)-(-)-2-benzyloxycyclopentyl isocyanate
Catalog Number:
737001-14-8
Synonyms:
(1R,2R)-(-)-2-BENZYLOXYCYCLOPENTYL ISOCYANATE
CAS Number:
737001-14-8
Molecular Weight:
217.26
Molecular Formula:
C13H15NO2
COA:
Inquire
MSDS:
Inquire
Chemical Structure
CAS 737001-14-8 (1R,2R)-(-)-2-benzyloxycyclopentyl isocyanate

Reference Reading


1.Synthesis of polymer-type chiral stationary phases and their enantioseparation evaluation by high-performance liquid chromatography.
Huang SH1, Bai ZW, Yin CQ, Li SR, Pan ZQ. Chirality. 2007 Feb;19(2):129-40.
Two new chiral polymers of different molecular weights were synthesized by the copolymerization of (1R,2R)-(+)-1,2-diphenylethylenediamine, phenyl diisocyanate and terephthaloyl chloride. The polymers were immobilized on aminated silica gel to afford two chiral stationary phases. The polymers and the corresponding chiral stationary phases were characterized by Fourier transform-IR, elemental analysis, 1H and 13C NMR. The surface coverages of chiral structural units on the chiral stationary phases were estimated as 0.27 and 0.39 mmol/g, respectively. The enantioseparation ability of these chiral stationary phases was evaluated with a variety of chiral compounds by high-performance liquid chromatography. The effects of the organic additives, the composition of mobile phases, and the injection amount of sample on enantioseparation were investigated. A comparison of enantioseparation ability between these two chiral stationary phases was made.
2.Liquid chromatographic enantioseparation of beta-blocking agents with (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate as chir
Péter M1, Gyéresi A, Fülöp F. J Chromatogr A. 2001 Mar 2;910(2):247-53.
The applicability of (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate [(R,R)-DANI] as a recently developed chiral derivatizing agent for the enantioseparation of a series of beta-blockers is described. The thiourea diastereomers formed were analyzed by reversed-phase high-performance liquid chromatography, mixtures of water and methanol or acetonitrile being used for elution. Conditions of derivatizations (temperature, reagent excess and reaction time) were optimized, and the effects of organic modifiers on the retention and separation were investigated; the diastereomers could readily be baseline separated with methanol-containing mobile phases with resolutions between 1.58 and 2.72.
3.Alterations in the stereochemistry of the kappa-selective opioid agonist U50,488 result in high-affinity sigma ligands.
de Costa BR1, Bowen WD, Hellewell SB, George C, Rothman RB, Reid AA, Walker JM, Jacobson AE, Rice KC. J Med Chem. 1989 Aug;32(8):1996-2002.
The synthesis and in vitro sigma receptor activity of the two diastereomers of U50,488 [(+/-)-2], namely, (1R,2S)-(+)- cis-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacet ami de [(+)-1] and (1S,2R)-(-)-cis-3,4-dichloro- N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide [(-)-1], are described. (+)-1 and (-)-1 were synthesized from (+/-)-trans-N-methyl-2-aminocyclohexanol [(+/-)-3]. Pyridinium chlorochromate (PCC) oxidation of the N-t-Boc-protected derivative of (+/-)-3 afforded (+/-)-2-[N- [(tert-butyloxy)carbonyl]-N-methylamino]cyclohexanone [(+/-)-5]. The sequence of enamine formation with pyrrolidine, catalytic reduction, N-deprotection, and optical resolution afforded (1R,2S)-(-)-cis-2-pyrrolidinyl-N-methylcyclohexylamine [(-)-10] and (1S,2R)-(+)-cis-2-pyrrolidinyl-N-methylcyclohexylamine [(+)-10]. The optical purity (greater than 99.5%) of (-)-10 and (+)-10 was determined by HPLC analysis of the diastereomeric ureas formed by reaction with optically pure (R)-alpha-methylbenzyl isocyanate.
4.[High performance liquid chromatographic enantiomer separation of beta-blocking agents with a new isothiocyanate type chiral derivatizing agent].
Gyéresi A1, Péter M, Fülöp F. Acta Pharm Hung. 2000 Jul-Dec;70(3-6):138-45.
The applicability of (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propyl isothiocyanate [(R,R)-DANI] as a recently developed chiral derivatizing agent for the enantioseparation of a series of beta-blockers is described. The thiourea diastereomers formed were analysed by reversed-phase high-performance liquid chromatography, mixtures of water and methanol or acetonitrile being used for elution. Conditions of derivatizations (temperature, reagent excess and reaction time) were optimized. The effects of organic modifiers on the retention and separation were investigated; the diastereomers could readily be baseline-separated with methanol-containing mobile phases. The reagent allowed the detection of all four stereoisomers of labetalol, which has two chiral centres.