174823-32-6

Basic information

• Product Name: (1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl
• Synonyms: (1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl;(1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.2]OCTANE HYDROCHLORIDE,98%
• CAS NO: 174823-32-6
• Molecular Formula: C11H21ClN2O2
• Molecular Weight: 248.74964
• Mol File: 174823-32-6.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl(174823-32-6)
• EPA Substance Registry System: (1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl(174823-32-6)

Safety Data

• Hazardous Substances Data: 174823-32-6(Hazardous Substances Data)

Usage

General Description

The chemical "(1S)-2,5-Diazabicyclo[2.2.2]octane-2-carboxylic acid 1,1-dimethylethyl ester . HCl" is a compound that consists of a 2,5-diazabicyclo[2.2.2]octane core with both a carboxylic acid and a 1,1-dimethylethyl ester functional group attached. The compound is in the form of a hydrochloride salt. It is commonly used as a catalyst in organic synthesis reactions, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. It is known for its ability to facilitate a range of reactions and is widely utilized in the pharmaceutical industry for the synthesis of various drugs and pharmaceutical intermediates. Additionally, it has applications in the production of agrochemicals, flavors, fragrances, and other fine chemicals.

Upstream product

• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 100944-15-8 (1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 116258-17-4 (1R,4R)-5-phenylmethyl-2,5-diazabicyclo[2.2.1] heptane dihydrobromide 
• 387362-68-7 tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-formate 
• 31560-25-5 5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane 
• 31560-19-7 (2S,4R)-1-benzoyl-4-hydroxy-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 120806-96-4 (2S,4S)-1-benzoyl-4-hydroxyproline methyl ester 
• 326596-46-7 (4S,2R)-4-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 134003-83-1 tert-butyl (1R,4R)-5-benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 

Downstream Products

• 286943-81-5 (1R,4R)-2-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane 
• 286943-21-3 (1S,4S)-2-(6-methyl-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane 
• 244768-98-7 2-tert-butoxycarbonyl-5-methyl-2,5-diazabicyclo[2.2.1]heptane 
• 1255708-36-1 C₁₈H₂₂F₂N₂O₃ 
• 1255708-32-7 C₂₀H₂₉N₃O₃ 
• 1186334-65-5 (1S,4S)-tert-butyl 5-(4-acetyl-3-methylphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 1255708-39-4 C₁₈H₂₀F₄N₂O₃ 
• 1255708-33-8 C₁₈H₂₃FN₂O₃ 
• 1255708-30-5 C₁₈H₂₃BrN₂O₃ 
• 1186334-97-3 tert-butyl (1S,4S)-5-(4-acetylphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 
• 1255708-37-2 C₁₈H₂₂F₂N₂O₃ 
• 1255708-31-6 C₁₉H₂₃F₃N₂O₃ 
• 1255708-40-7 C₁₈H₂₄N₂O₃ 
• 1255708-38-3 C₁₈H₂₂F₂N₂O₃ 

Relevant articles and documents

Method for preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

The invention discloses a method for preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane. The method comprises the following steps: (1) preparing an intermediate I by using N-Boc-trans-4-hydroxy-L-proline methyl ester as a raw material; (2) preparing an intermediate II by reacting the intermediate I with an organic base and a sulfonylating reagent; (3) preparing an intermediate III from the intermediate II and benzylamine; and (4) finally preparing (1S, 4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane by debenzylating the intermediate III. The method provided by the invention simplifies reaction steps, reduces raw material cost and time cost, has high product yield, tends to purify and amplify production, and can reduce waste discharge.

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.

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.