134003-84-2

Basic information

• Product Name: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
• Synonyms: 1,1-Dimethylethyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;tert-Butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;(1R,4R)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;(1R,4R)-2-Boc- 2,5-diazabicyclo[2.2.1]heptane-HCl;(1R,4R)-tert-butyl 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate HCl 134003-84-2;(1R,4R);tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride;tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride
• CAS NO: 134003-84-2
• Molecular Formula: C10H19ClN2O2
• Molecular Weight: 234.72306
• Mol File: 134003-84-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 276.4±15.0 °C(Predicted)
• Appearance: /
• Density: 1.104±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.74±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride(134003-84-2)
• EPA Substance Registry System: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate hydrochloride(134003-84-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 134003-84-2(Hazardous Substances Data)

Usage

Uses

(1R,4R)-5-Boc-2,5-diazabicyclo[2.2.1]heptane is a useful reagent employed in the preparation of tetrahydroisoquinolines as CXCR4 antagonists.

InChI:InChI=1/C10H18N2O2.ClH/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7;/h7-8,11H,4-6H2,1-3H3;1H/t7-,8-;/m1./s1

Upstream product

• 591-50-4 iodobenzene 
• 137-07-5 2-amino-benzenethiol 
• 1527-12-4 2-(phenylthio)benzoic acid 
• 108-95-2 phenol 
• 882-33-7 diphenyldisulfane 
• 14178-42-8 2-benzamidopyridine 1-oxide 
• 4171-83-9 2-nitrophenyl phenyl sulfide 
• 88-73-3 2-Chloronitrobenzene 
• 108-98-5 thiophenol 
• 1134-94-7 2-phenylsulfanyl-aniline 
• 1885-14-9 phenyl chloroformate 
• 387362-68-7 tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-formate 
• 326596-46-7 (4S,2R)-4-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 116258-17-4 (1R,4R)-5-phenylmethyl-2,5-diazabicyclo[2.2.1] heptane dihydrobromide 

Downstream Products

• 286946-75-6 tert-butyl (1R,4R)-5-(5-benzyloxy-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 198988-90-8 (1R,4R)-2-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptane 
• 1195065-89-4 4-((1R,4R)-5-isopropyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)aniline 

Relevant articles and documents

INFLUENZA VIRUS REPLICATION INHIBITOR AND USE THEREOF

Disclosed are a compound as shown in formula (I) as an influenza virus replication inhibitor and a preparation method therefor, a pharmaceutical composition comprising the compound and the use of the compound and pharmaceutical composition thereof in the treatment of influenza.

Design, synthesis and anticancer activity of N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives

Novel N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives were designed, synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR and Mass spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including K562, Colo-205 and MDA-MB 231 by MTT assay. The screening results showed that five compounds (16b, 16d, 16i, 16p and 16q) exhibited potent cytotoxic activities with IC50 values between 20 and 40 μM. Further in vitro studies revealed that inhibition of sirtuins could be the possible mechanism of action of these molecules.

Synthesis of (1R,4R)-2,5-diazabicyclo[2.2.1]heptane derivatives by an epimerization-lactamization cascade reaction

An epimerization-lactamization cascade of functionalized (2S,4R)-4-aminoproline methyl esters is developed and applied in synthesizing (1R,4R)-2,5-diazabicyclo[2.2.1]heptane (DBH) derivatives. (2S,4R)-4-Aminoproline methyl esters are likely to undergo 2-epimerization under basic conditions, followed by an intramolecular aminolysis of the (2R)-epimer to form the bridged lactam intermediates. Key factors identified for this cascade reaction include the electron-withdrawal N-protective group in the substrates and a strong base as the promoter.