242482-28-6

Basic information

• Product Name: 2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine
• Synonyms: 2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine;2-[(4R)-4-tert-Butyl-4,5-dihydro-2-oxazolyl]pyridine;2-[(4R)-4,5-dihydro-4-(1,1-dimethylethyl)-2-oxazolyl]-Pyridine;2-[(4R)-4-tert-Butyl-4,5-dihydro-2-oxazolyl]pyridine,99%e.e.
• CAS NO: 242482-28-6
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.26824
• Mol File: 242482-28-6.mol

Chemical Properties

• Boiling Point: 314.6±15.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.79±0.70(Predicted)
• CAS DataBase Reference: 2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine(242482-28-6)
• EPA Substance Registry System: 2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine(242482-28-6)

Safety Data

• Hazardous Substances Data: 242482-28-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[(4R)-4-(1,1-dimethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique reactivity and biological activity contribute to the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 2-[(4R)-4-(1,1-dimethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine is utilized as a building block for the creation of novel agrochemicals. Its incorporation into these compounds can lead to enhanced pest control and crop protection, ultimately benefiting agricultural productivity.
Used in Medicinal Chemistry Research:
2-[(4R)-4-(1,1-dimethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine is employed as a valuable research tool in medicinal chemistry. Its unique properties allow scientists to explore new avenues in drug discovery and design, potentially leading to the development of innovative therapeutic agents.
Used in Chemical Biology Research:
2-[(4R)-4-(1,1-diMethylethyl)-4,5-dihydro-2-oxazolyl]-Pyridine also plays a significant role in chemical biology research, where it is used to study the interactions between small molecules and biological targets. Its presence can provide insights into the mechanisms of action and help in the design of more effective biologically active molecules.

Upstream product

• 112245-13-3 (S)-tert-leucinol 
• 19547-38-7 methyl pyridine-2-imidate 
• 3907-02-6 2‐amino‐3,3‐dimethylbutan‐1‐ol 
• 41050-95-7 ethyl picolinimidate 
• 100-70-9 2-Cyanopyridine 
• 33105-81-6 2-amino-3,3-dimethylbutanoic acid 
• 98-98-6 2-Picolinic acid 
• 20859-02-3 L-tert-Leucine 
• 29745-44-6 pyridine-2-carbonyl chloride 

Relevant articles and documents

Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**

A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.

A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5- dihydrooxazole ((S)-t-BuPyOx) ligand

An efficient method for the synthesis of the (S)-4-(tert-butyl)-2-(pyridin- 2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand has been developed. Inconsistent yields and tedious purification in known routes to (S)-t-BuPyOx suggested the need for an efficient, dependable, and scalable synthetic route. Furthermore, a route suitable for the synthesis of PyOx derivatives is desirable. Herein, we describe the development of a three-step route from inexpensive and commercially available picolinic acid. This short procedure is amenable to multi-gram scale synthesis and provides the target ligand in 64% overall yield.

Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: Insights from computation and experiment

Enantioselective conjugate additions of arylboronic acids to β-substituted cyclic enones have been previously reported from our laboratories. Air- and moisture-tolerant conditions were achieved with a catalyst derived in situ from palladium(II) trifluoroacetate and the chiral ligand (S)-t-BuPyOx. We now report a combined experimental and computational investigation on the mechanism, the nature of the active catalyst, the origins of the enantioselectivity, and the stereoelectronic effects of the ligand and the substrates of this transformation. Enantioselectivity is controlled primarily by steric repulsions between the t-Bu group of the chiral ligand and the α-methylene hydrogens of the enone substrate in the enantiodetermining carbopalladation step. Computations indicate that the reaction occurs via formation of a cationic arylpalladium(II) species, and subsequent carbopalladation of the enone olefin forms the key carbon-carbon bond. Studies of nonlinear effects and stoichiometric and catalytic reactions of isolated (PyOx)Pd(Ph)I complexes show that a monomeric arylpalladium-ligand complex is the active species in the selectivity-determining step. The addition of water and ammonium hexafluorophosphate synergistically increases the rate of the reaction, corroborating the hypothesis that a cationic palladium species is involved in the reaction pathway. These additives also allow the reaction to be performed at 40 C and facilitate an expanded substrate scope.

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors

Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

Efficient enhancement of copper-pyridineoxazoline catalysts through immobilization and process design

Copper-pyridineoxazoline (Cu-pyox) complexes are poor homogeneous catalysts for asymmetric cyclopropanation reactions. Pyox ligands have been immobilized by polymerization of monomers possessing a vinyl group directly attached to position 6 with styrene a

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters

The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst

Asymmetric Catalysis, 45. - Enantioselective Hydrosilylation of Ketones with 2/Pyridinyloxazoline Catalysts

21 optically active 2-(2-pyridinyl)oxazolines are synthesized from 2-cyanopyridine and optically pure amino alcohols.The new pyridinyloxazolines are used as cocatalysts together with 2 as homogeneous in situ catalysts in the enantioselective hydrosilylation of prochiral ketones with diphenylsilane.After hydrolysis, 1-phenylethanol is produced in 83.4percent ee from acetophenone.Another three ketones are included into these investigations.The optical purity depends on the rhodium/ligand, rhodium/ketone, and ketone/silane ratio as well as on the solvent.Compared with other organic solvents, hydrosilylations in the solvent CCl4 without exceptions result in better chemical yields and optical purities as consequence of a change in the catalytically active species due to oxidative addition of CCl4. - Keywords: Enantioselective hydrosilylation/ Optically active secondary alcohols/ Rhodium/ pyridinyloxazoline catalysts