78792-49-1

Upstream product

• 794-05-8 1,2-diphenyl-2-(1-piperidinyl)ethanone 
• 110-89-4 piperidine 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 1484-50-0 desyl bromide 
• 6281-83-0 α-piperidino-deoxybenzoin; hydrochloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 447-31-4 Desyl chloride 
• 1439-07-2 trans-Stilbene oxide 

Downstream Products

• 17243-73-1 ((RS,SR)-α'-hydroxy-bibenzyl-α-yl)-1-methyl-piperidinium; iodide 

Relevant academic research and scientific papers

Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines

Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F

Planar chiral PHANOLs as double hydrogen bonding donor organocatalysts: Synthesis and catalysis

4,12-Dihydroxy[2.2]paracyclophanediol (PHANOL; 1), and its para-substituted derivatives 2, 5 and 7, were found to catalyse Diels-Alder cyclo-additions of α,β-unsaturated aldehydes or ketones with dienes and/or epoxide ring opening reactions with amines. The mode of catalysis by the PHANOLs is via double hydrogen bonding to the two sp2 lone pairs of a carbonyl group or the two lone pairs of the epoxide. The order of activity of the PHANOLs for catalysis of the Diels-Alder reaction essentially correlates with the expected hydrogen-bond donor strength based on the degree of electron-withdrawing capability of the group(s) in the para position. In contrast, ortho-substituted PHANOLs 10, 11 and 14 were not active as catalysts due to steric interference with the double hydrogen bonding mode. 1H NMR and IR spectral data for the various PHANOLs are discussed in support of the proposed double hydrogen bond mode.

Photochemistry of Intramolecular Charge Transfer Excited States in Donor-Acceptor-Substituted Diamines

The photochemistry and photophysics of 1,2-diamines C5H10NCHPhCHPhNHC6H4R (1, R=CN, and 2, R=4-pyridyl) have been examined.These compounds display a strong absorption band in the near-UV which is due to intramolecular charge transfer from the secondary amine group to the 4-cyanophenyl or (4-pyridyl)phenyl acceptor unit.Photoexcitation into this absorption band leads to moderately intense fluorescence from the 1LE state of the charge transfer chromophore and to homolytic bond fragmentation across the 1,2 C-C bond with moderate quantum efficiency.Detailed photochemical and photophysical studies reveal that the bond fragmentation reaction ensues from a second intramolecular charge transfer excited state (denoted 1CT) which is based on electron transfer from the tertiary piperidine nitrogen to the 4-cyanophenyl or (4-pyridyl)phenyl unit.Photochemical product analysis reveals that erythro -> threo (or threo -> erythro) isomerization occurs under both argon-degassed and air-saturated conditions.This observation indicates that recombination of the radicals formed by bond fragmentation occurs, both within the geminate pair and between free radicals that have escaped the solvent cage.Analysis of fluorescence, transient absorption, and steady-state photochemical kinetics data indicates that (1) internal conversion from the 1LE state to the 1CT state by intramolecular electron transfer occurs with k>/=109 s-1 in all of the diamines; (2) bond fragmentation within the 1CT state occurs with k>/=108 s-1 in each of the diamines; (3) bond fragmentation may be faster in erythro-1 than in threo-1.

1,2-diarylethylamines for treatment of neurotoxic injury

Compounds, compositions and methods of treatment are described to control brain damage associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of a 1,2-diarylethylamine compound as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites. Compounds of interest are those of the formula wherein each of R1 and R2 is a group independently selected from hydrido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, hydroxyl, alkoxy, halo, cyano, nitro and mercapto, or wherein R1 and R2 may be taken together to form an oxo group or to form a saturated or partially unsaturated carbocyclic group having three to eight ring carbons; wherein each of Ar1 and Ar2 is a group independently selected from aryl and heteroaryl having one or two heteroatoms selected from N, O and S; and wherein any of the foregoing Ar1 and Ar2 groups having a substitutable position msy be substituted with one or more radicals selected from hydrido, alkyl, cycloalkyl, halo, haloalkyl, alkenyl, alkynyl, hydroxyl, hydroxyalkyl, alkoxy, alkoxyalkyl, amino, cyano, nitro and mercapto; wherein X is selected from CH, CH2, NH, O and S, to form a ring having five to eight members provided that such ring is saturated or contains one double bond or is benzo-fused; and wherein Y is one or more a groups selected from hydrido, alkyl, cycloalkyl, halo, haloalkyl, alkenyl, alkynyl, hydroxyl, hydroxy-alkyl, alkoxy, alkoxyalkyl, amino, cyano, nitro and mercapto; or a pharmaceutically acceptable salt thereof.