133097-95-7

Basic information

• Product Name: (1R,4R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane
• Synonyms: (1R,4R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane;(1R,4R)-5-Methyl-2,5-diazabicyclo[2.2.1]heptane
• CAS NO: 133097-95-7
• Molecular Formula: C₆H₁₂N₂
• Molecular Weight: 112.17288
• Mol File: 133097-95-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 159.6±8.0 °C(Predicted)
• Appearance: /
• Density: 0.998±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.48±0.20(Predicted)
• CAS DataBase Reference: (1R,4R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane(133097-95-7)
• EPA Substance Registry System: (1R,4R)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane(133097-95-7)

Safety Data

• Hazardous Substances Data: 133097-95-7(Hazardous Substances Data)

Usage

General Description

(1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane is a chemical compound that belongs to the class of diazabicyclo[2.2.1]alkanes. It is a bicyclic organic compound with the molecular formula C7H12N2. This chemical is chiral and exists as a pair of enantiomers, with (1R,4R)-2-methyl-2,5-diazabicyclo[2.2.1]heptane being the (R,R)-enantiomer. It is used in organic synthesis as a chiral base and ligand in asymmetric catalysis, especially in the formation of carbon-carbon and carbon-nitrogen bonds. It has also been investigated for its potential use in medicinal chemistry, particularly in the development of new pharmaceuticals.

Upstream product

• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 244768-98-7 2-tert-butoxycarbonyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 
• 179694-15-6 (1S,4S)-2-benzyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 

Downstream Products

• 767291-68-9 (1S,4S)-(+)-2,5-dimethyl-2,5-diazabicyclo[2.21]heptane 
• 1116571-76-6 C₁₆H₂₄N₂O₂S 
• 1116571-78-8 C₁₄H₂₀N₂O₂S 
• 1220095-03-3 C₁₇H₂₆N₂O₂S 
• 1116571-80-2 C₁₂H₁₅ClN₂O₂S 
• 1116571-79-9 C₁₃H₁₈N₂O₃S 
• 1235469-91-6 (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooctadec-9-en-7-yl phenylacetate 
• 1338705-94-4 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(((1S,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-yl)methyl)benzamide 
• 138808-76-1 danofloxacin mesylate 

Relevant articles and documents

Inhibitors of Bruton's Tyrosine Kinase

This application discloses 6-(2-Hydroxymethyl-phenyl)-2-methyl-2H-pyridazin-3-one derivatives according to generic Formula I: wherein, variables X, R, and Y4, are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation, such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.

Azabicyclic sulfonamides as potent 11β-HSD1 inhibitors

Inhibition of 11β-HSD1 has demonstrated potential in the treatment of various components of metabolic syndrome. We wish to report herein the discovery of novel azabicyclic sulfonamide based 11β-HSD1 inhibitors. Highly potent compounds exhibiting inhibitor

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.