134003-03-5

Basic information

• Product Name: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE
• Synonyms: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE;(1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE 95%, (98% E.E.);(1s,4R)-2-Azabicyclo[2.2.1]heptan-3-one, 95%, ee:98%;(1S,4R)-2-Azabicyclo[2.2.1]heptan-3-one, 98% ee
• CAS NO: 134003-03-5
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• Mol File: 134003-03-5.mol

Chemical Properties

• Melting Point: 76.2 °C
• Boiling Point: 208.27°C (rough estimate)
• Flash Point: 160.9°C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.0656 (rough estimate)
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.4729 (estimate)
• CAS DataBase Reference: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(134003-03-5)
• EPA Substance Registry System: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(134003-03-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 134003-03-5(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow crystalline powder

InChI:InChI=1/C6H9NO/c8-6-4-1-2-5(3-4)7-6/h4-5H,1-3H2,(H,7,8)/t4-,5+/m1/s1

Upstream product

• 95936-41-7 (-)-6endo,7anti-Dibromo-2-azabicyclo<2.2.1>heptan-3-one 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 

Downstream Products

• 151792-53-9 tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 180323-49-3 (1R,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride 
• 625108-11-4 C₇H₁₃NO₂ 
• 674303-50-5 (1S,9R)-2,7-diazatricyclo[7.2.1.0^2,8]dodec-7-ene 
• 674303-51-6 (1S,8R)-2,6-diazatricyclo[6.2.1.0^2,7]undec-6-ene 
• 664341-72-4 (1S,4R)-1-tert-butoxycarbonylamino-4-hydroxymethylcyclopentane 
• 117957-62-7 (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone 
• 859147-57-2 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 859147-53-8 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine 
• 859147-55-0 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-2',3'-O-isopropylideneadenosine 
• 859147-59-4 N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 674303-45-8 (1R,4S)-3-{(3S)-3-azido-3-phenylpropyl}-3-azabicyclo[2.2.1]heptan-2-one 
• 71830-07-4 (1S,3R)-3-aminocyclopentanecarboxylic acid 

Relevant articles and documents

Synthesis and evaluation of cyclopentane-based muraymycin analogs targeting MraY

Antibiotic resistance is one of the most challenging global health issues and presents an urgent need for the development of new antibiotics. In this regard, phospho-MurNAc-pentapeptide translocase (MraY), an essential enzyme in the early stages of peptid

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.

METHODS OF RATIONAL NICOTINE HAPTEN DESIGN AND USES THEREOF

Provided herein are methods for rational design of nicotine haptens. More particularly, provided herein are methods for designing, selecting, and synthesizing nicotine haptens and nicotine hapten conjugates. Also provided herein are novel nicotine haptens and methods for using nicotine haptens to treat nicotine addiction.

CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS

The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.

Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.

NOVEL SUBSTITUTED INDANES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS DRUGS

The invention relates to substituted indanes and derivatives thereof, to physiologically acceptable salts and physiologically functional derivatives thereof, to the production thereof, to drugs containing at least one substituted indane according to the invention or derivative thereof, and to the use of the substituted indanes according to the invention and to derivatives thereof as MCH antagonists.

Design, synthesis, and structure-activity relationship of novel CCR2 antagonists

A series of novel 1-aminocyclopentyl-3-carboxyamides incorporating substituted tetrahydropyran moieties have been synthesized and subsequently evaluated for their antagonistic activity against the human CCR2 receptor. Among them analog 59 was found to posses potent antagonistic activity.

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.

Synthesis of stable and cell-type selective analogues of cyclic ADP-ribose, a Ca2+-mobilizing second messenger. Structure-activity relationship of the N1-ribose moiety

We previously developed cyclic ADP-carbocyclic ribose (cADPcR, 2) as a stable mimic of cyclic ADP-ribose (cADPR, 1), a Ca2+-mobilizing second messenger. A series of the N1-ribose modified cADPcR analogues, designed as novel stable mimics of cAD

Enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]hept- 5-enes by hetero Diels-Alder addition to cyclopentadiene

Diels-Alder cycloaddition of N-benzyl imine of (1R)-8-phenylmenthyl glyoxylate to cyclopentadiene gave the mixture of adducts 3a-d. Major diastereoisomer, the (1S,exo)-adduct (3a), was isolated in 57% yield and transformed in 74% overall yield into (+)-(1