N,N-diethylpropan-2-amine

Name: N,N-diethylpropan-2-amine
SKU: ACM6006151
Rating: 5 (1 reviews)

CAS

6006-15-1

Catalog Number

ACM6006151

Category

Main Products

Molecular Weight

115.22

Molecular Formula

C7H17N

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Specification

Synonyms

2-propanamine, N,N-diethyl-; 2-Propaneamine, N,N-diethyl-; Diethylisopropylamine; N,N-Diethyl-2-propanamine; N,N-Diethylpropan-2-amine

Boiling Point

104.7 °C at 760 mmHg

Flash Point

6 °C

N,N-diethylpropan-2-amine for the synthesis of potential adenosine receptor ligands

Synthesis and characterisation of new 4-oxo-N-(substituted-thiazol-2-yl)-4H-chromene-2-carboxamides

Cagide, Fernando, et al. Journal of Molecular Structure 1089 (2015): 206-215.

Chromones are 4H-benzopyran-4-one heterocycles that have been intensively studied due to their biological activity. Thiazole-based compounds have long been used as therapeutic agents, as antibacterial, antiviral and antifungal agents, but in the last decades they have been identified as potent and selective ligands for adenosine receptors. A series of new chromone-thiazole hybrids as potential ligands for human adenosine receptors have been synthesized using N,N-diethylpropan-2-amine, among others. In this case, new 4-oxo-N-(substituted-thiazol-2-yl)-4H-chromone-2-carboxamides were synthesized from chromone-2-carboxylic acid by two different amidation approaches. The development of different synthetic methods offers the possibility to work under different reaction conditions, i.e. using conventional heating and/or microwave irradiation. The structures of the compounds were established on the basis of NMR and MS spectroscopy as well as X-ray crystallography. Data related to the molecular geometry and conformation of chromone-thiazole hybrids have been obtained, which are crucial for understanding ligand-receptor binding.
To a solution of chromone-2-carboxylic acid (1 g, 5.26 mmol) in DMF (12 mL) at 4 °C was added a solution of N,N-diethylpropan-2-amine (0.92 ml, 5.26 mmol) and PyBOP (2.73 mg, 5.26 mmol) in CHCl (12 mL). The mixture was kept in an ice bath and stirred for half an hour. After this period, thiazole-2-amine (526 mg, 5.26 mmol) was added and the mixture was then allowed to warm to room temperature. The reaction was kept under stirring for 4 hours.

N,N-diethylpropan-2-amine for dual TLR7/TLR8 antagonist studies

Shukla, Nikunj M., et al. Bioorganic & medicinal chemistry 19.12 (2011): 3801-3811.

Toll-like receptors (TLR)-7 and -8 are thought to play important roles in immune activation processes underlying the pathophysiology of HIV and several clinically important autoimmune diseases. Based on the earlier discovery of TLR7 antagonistic activity in 3H-imidazoquinolines, an attempt was made to examine a pilot library of 3H-imidazolines for dual TLR7/8 antagonists, as they remain an understudied chemotype. Two-dimensional NOE experiments were employed to unambiguously characterize the compounds. Quinoline compound 12, bearing methoxybenzyl substituents at the N3 and N5 positions, was identified as a lead compound. Compound 12 was found to inhibit both TLR7 and TLR8 at low micromolar concentrations. To determine whether 12 was a quinoline or imidazoline species, the 1H regioisomer 17 was synthesized using N,N-diethylpropan-2-amine for study.
To a mixture of 14 (147 mg, 0.71 mmol) in toluene and 2-propanol was added a solution of N,N-diethylpropan-2-amine (0.14 mL, 6 mmol) and 15 (121 mg, 0.88 mmol). The reaction mixture was heated to 70 °C for half an hour until solids began to precipitate. The reaction mixture was then cooled, filtered and washed with toluene/2-propanol (7:3), ether and cold water. The residue was dried at 80 °C to give compound 16 (200 mg, 91%).

Synthesis and related biological experimental studies of rotolone analogs using N,N-diethylpropan-2-amine

Zhang, Yinan, et al. Molecules 26.4 (2021): 1024.

The study found that demethyl xanthohumol inhibited α-glucosidase in vitro. Further studies showed that dehydrocyclomethyl xanthohumol and its dimer analog rotolone exhibited more potent α-glucosidase inhibitory activity than 1. The purpose of the study was to synthesize a series of rotolone analogs using N,N-diethylpropan-2-amine and evaluate their dual inhibitory activities against α-glucosidase and DPP-4. The results showed that compounds 4d and 5d irreversibly and effectively inhibited α-glucosidase and moderately inhibited DPP-4. In addition, compounds 4d and 5d significantly promoted glucose consumption, and the activity of 5d at 0.2 μM was comparable to that of metformin at a concentration of 1 mM.
1-(2,4,6-Trihydroxyphenyl)ethane-1-one (1.68 g, 10 mmol) was dissolved in anhydrous CH2Cl2 (100 mL) at 0 ◦C, and N,N-diethylpropan-2-amine (3.93 g, 25 mmol) and chloro(methoxy)methane (1.77 g, 22 mmol) were added. The reaction mixture was warmed to room temperature and then stirred for 6 hours. The reaction was quenched with NH4Cl (aq) and extracted three times with CH2Cl2 (500 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate 20:1) to give 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)ethane-1-one (2.1 g, 82%) as a colorless oil. 1-(2-Hydroxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one (1.28 g, 5 mmol) was dissolved in MeOH (50 mL) at 0 ◦C and 2 N HCl (5 mL) was added. After addition, the reaction mixture was heated to 40 ◦C and then stirred for 3 hours. The reaction was quenched with NaHCO3 (aq) and extracted three times with EtOAc (100 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure.

Synthesis of a novel mitochondrial permeability transition pore (mPTP) inhibitor using N,N-diethylpropane-2-amine

Synthetic strategy pursued for AntiOxBEN3 development.

Teixeira, José, et al. Journal of enzyme inhibition and medicinal chemistry 33.1 (2018): 567-576.

Pharmacological interventions targeting mitochondria have several obstacles that prevent them from achieving their full efficacy. Therefore, a novel mitochondrial-affinity antioxidant (AntiOxBEN3) based on the dietary antioxidant gallic acid was synthesized using N,N-diethylpropane-2-amine. AntiOxBEN3 accumulated thousands-fold within isolated rat liver mitochondria without disrupting the oxidative phosphorylation apparatus, with respiratory control rates, phosphorylation efficiency, and transmembrane potential remaining unchanged. AntiOxBEN3 also showed limited toxicity to human hepatoma cells. Furthermore, AntiOxBEN3 exhibited potent iron chelating and antioxidant properties in both isolated liver mitochondria and cultured rat and human cell lines. In addition to low toxicity and high antioxidant activity, AntiOxBEN3 strongly inhibited the calcium-dependent opening of the mitochondrial permeability transition pore (mPTP).
To a solution of compound 4 (689 mg, 2.2 mmol) in DMF (7.4 ml) was added a solution of N,N-diethylpropan-2-amine (0.476 ml, 2.7 mmol) and PyBOP (1572 mg, 2.7 mmol) in CH2Cl2 (7.4 ml) at 4°C. The mixture was stirred in an ice bath for half an hour. Thereafter, compound 5 (1218, 2.7 mmol) was added and the reaction was then heated to room temperature. The reaction was stirred for 20 hours. The mixture was then diluted with AcOEt (40 ml) and washed with saturated NaHCO3 solution (2 10 ml). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (10% MeOH/CH2Cl2).

What is the molecular formula of N,N-diethylpropan-2-amine?

The molecular formula of N,N-diethylpropan-2-amine is C7H17N.

What are the synonyms for N,N-diethylpropan-2-amine?

The synonyms for N,N-diethylpropan-2-amine are Diethylisopropylamine, 6006-15-1, N,N-Diethyl Isopropyl Amine, and 2-Propanamine, N,N-diethyl-.

What is the molecular weight of N,N-diethylpropan-2-amine?

The molecular weight of N,N-diethylpropan-2-amine is 115.22 g/mol.

When was N,N-diethylpropan-2-amine created?

N,N-diethylpropan-2-amine was created on March 27, 2005.

When was N,N-diethylpropan-2-amine last modified?

N,N-diethylpropan-2-amine was last modified on October 21, 2023.

What is the IUPAC name of N,N-diethylpropan-2-amine?

The IUPAC name of N,N-diethylpropan-2-amine is N,N-diethylpropan-2-amine.