59436-75-8

Basic information

• Product Name: (1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane
• Synonyms: (1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane;2-Benzyl-5-tosyl-2,5-diaza-bicyclo[2.2.1]heptane;6-Benzyl-3-(4-methylphenyl)sulfonyl-3,6-diazabicyclo[2.2.1]heptane
• CAS NO: 59436-75-8
• Molecular Formula: C19H22N2O2S
• Molecular Weight: 342.46
• Mol File: 59436-75-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 482.4 °C at 760 mmHg
• Flash Point: 245.5 °C
• Appearance: /
• Density: 1.272
• Vapor Pressure: 1.84E-09mmHg at 25°C
• Refractive Index: 1.634
• PKA: 7.41±0.20(Predicted)
• CAS DataBase Reference: (1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane(59436-75-8)
• EPA Substance Registry System: (1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane(59436-75-8)

Safety Data

• Hazardous Substances Data: 59436-75-8(Hazardous Substances Data)

Usage

General Description

(1S,4S)-2-benzyl-5-tosyl-2,5-diazabicyclo[2.2.1]heptane, also known as DABCO, is a bicyclic organic compound with a diazabicyclic core structure. It is commonly used as a catalyst and a ligand in organic synthesis due to its ability to facilitate a variety of chemical reactions. DABCO is known for its versatile reactivity, and it is often utilized in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and properties make it valuable in a wide range of applications within the chemical industry. Additionally, DABCO has potential applications in material science and as an additive in polymerization reactions.

InChI:InChI=1/C19H22N2O2S/c1-15-7-9-19(10-8-15)24(22,23)21-14-17-11-18(21)13-20(17)12-16-5-3-2-4-6-16/h2-10,17-18H,11-14H2,1H3

Upstream product

• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 100-46-9 benzylamine 
• 57850-05-2 (2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 141850-60-4 (2S,4R)-(1-tosyl-4-(tosyloxy)pyrrolidin-2-yl)methyl 4-methylbenzenesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 125109-59-3 (2R,4S)-4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 2584-71-6 cis-hydroxy-D-proline 
• 96763-06-3 1-(4-toluenesulfonyl)-2-(4-toluenesulfonyloxymethyl)-4-(4-toluenesulfonyloxy)-pyrrolidine 
• 116143-08-9 (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine 
• 116143-05-6 allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester 
• 116143-06-7 4-(acetyloxy)-1-<(4-methylphenyl)sulfonyl>-D-proline ethyl ester 

Downstream Products

• 132666-68-3 (1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane 

Relevant articles and documents

Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation

The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity

Multicomponent synthesis of some new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro anti-proliferative activity against CaSki, MDA-MB-231 and SK-Lu-1 tumour cells as apoptosis inducing agents without necrosis

Identification of a new class of antitumor agent capable to induce apoptosis without triggering necrotic cell death event is challenging. The present communication describes the multicomponent synthesis of seven new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro antiproliferative activity on cervical cancer cell line (CaSki), breast cancer cell line (MDA-MB231), lung cancer cell line (SK-Lu-1) and human lymphocytes. Among the synthesized dithiocarbamates, compound 9e displayed significant antiproliferative activity without inducing any necrotic cell death (both on tumour cells and lymphocytes) and induced apoptosis in tumor cells by the caspase dependent apoptotic pathway. The compound 9e also exhibited greater tumor selectivity than human lymphocytes. In silico ADME predictions revealed that compound 9e has the potential to be developed as a drug candidate. Rapid chemical modifications of this lead are thus highly necessary for further investigation as a drug like safer antitumor candidate and also to achieve compounds with better activity profile.

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