141294-37-3

Basic information

• Product Name: (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine
• Synonyms: (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine
• CAS NO: 141294-37-3
• Molecular Weight: 205.343
• Mol File: 141294-37-3.mol

Chemical Properties

• CAS DataBase Reference: (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine(141294-37-3)
• EPA Substance Registry System: (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine(141294-37-3)

Safety Data

• Hazardous Substances Data: 141294-37-3(Hazardous Substances Data)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 31519-48-9 C₁₄H₂₁N 
• 630-19-3 pivalaldehyde 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 141393-92-2 (R)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine 
• 917-54-4 methyllithium 
• 254745-01-2 (R)-N-(2,2-dimethylpropylidene)-1-phenylethylamine 
• 31519-48-9 N-<3,3-Dimethyl-butyliden-(2)>-DL-α-phenyl-ethylamin 

Downstream Products

• 3850-30-4 (R)-1,2,2-trimethylpropylamine 
• 147852-31-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-N-((R)-1,2,2-trimethyl-propyl)-propionamide 
• 3907-04-8 Pinakolylamin-phthalsaeuremonoamid 

Relevant articles and documents

Step-efficient access to chiral primary amines

Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines. Georg Thieme Verlag Stuttgart New York.

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.

Asymmetric reductive amination: Convenient access to enantioenriched alkyl-alkyl or aryl-alkyl substituted α-chiral primary amines

A two-step procedure for producing optically active, high value primary amines has been developed. The first and key step is the asymmetric reductive amination of a prochiral alkyl alkyl (acyclic or cyclic) or aryl alkyl (acyclic or cyclic) ketone with (R

Influence of bulky substituents on histamine H3 receptor agonist/antagonist properties

Novel derivatives of 3-(1H-imidazol-4-yl)propanol were designed on the basis of lead compounds belonging to the carbamate or ether series possessing (partial) agonist properties on screening assays of the histamine H3 receptor. One pair of enantiomers in the series of α-methyl-branched chiral carbamates was stereoselectively prepared in high optical yields. Enantiomeric purity was checked by Mosher amide derivatives of precursors and capillary electrophoresis of the final compounds with trimethyl-β-cyclodextrin as chiral selector, and was determined to be ≥95%. The novel compounds were investigated in various histamine H3 receptor assays in vitro and in vivo. Some compounds displayed partial agonist activity on synaptosomes of rat brain cortex, whereas others exhibited antagonist properties only. Selected compounds were investigated in [125I]iodoproxyfan binding studies on the human histamine H3 receptor and showed high affinity in the nanomolar concentration range. Under in vivo conditions after oral administration to mice, some of the compounds exhibited partial or full agonist activity in the brain at low dosages. The (S)-enantiomer of one pair of chiral carbamates (9) proved to be the eutomer; thus, the (S)-enantiomer was selected for further pharmacological studies. In a peripheral in vivo test model in rats, measuring the level of inhibition of capsaicin-induced plasma extravasation, (S)-9 again proved its high oral agonist potency with full intrinsic activity (ED50 values of 0.07-0.1 mg/kg depending on tissue).

Asymmetric reduction of enantiopure imines with zinc borohydride: Stereoselective synthesis of chiral amines

The first application of zinc borohydride in the reduction of enantiopure imines for the stereoselective preparation of both the enantiomers of secondary amines is described. A possible explanation of the stereoselectivity and of the reaction mechanism is

Asymmetric addition of alkyllithium to chiral imines: α-Naphthylethyl group as a chiral auxiliary

The diastereoselective nucleophilic addition of alkyllithium to N- alkylidene-α-naphthylethylamine was carried out. In the presence of Lewis acids or Lewis bases, organolithiums reacted smoothly with imines to give the corresponding amines in high stereoselectivity (up to 100% de). Furthermore, the resulting optically active amines were found to be useful for asymmetric reactions as chiral ligands.

Structure-activity studies of potassium channel opening in pinacidil-type cyanoguanidines, nitroethenediamines, thioureas, and ureas

Potassium channel opening activity for pinacidil-type cyanoguanidines, nitroethenediamines, thioureas, and ureas, has been assessed through simultaneous measurement of spontaneous contractile activity and stimulation of 86Rb+ efflux from rat portal veins loaded with 86Rb+. The good correlation between these two effects suggests that the vasodilator activity of the compounds is directly attributable to an increased opening of potassium channels. The resulting quantitative in vitro data has been used to analyze the structure-activity relationships for potassium channel opening, allowing the biological activity to be rationalized in terms of a pharmacophore involving a hydrogen-bond-acceptor element, a hydrogen-bond- donor element, and a lipophilic binding group. A model for the binding of pinacidil-related compounds to their potassium channel receptor has been developed, and compounds designed to test this model have been synthesized and tested. Prototropic equilibria are implicated as playing a fundamental role in determining the hydrogen-bonding ability of the compounds, and conformational changes in the receptor are invoked to explain disparities in the chiral recognition of lipophilic groups in different compounds.