75866-72-7 Usage
Description
(S)-4-Benzyl-2-methyl-2-oxazoline, with the molecular formula C11H11NO, is a chiral organic compound belonging to the class of oxazolines. These heterocyclic compounds feature an oxazole ring containing nitrogen and oxygen atoms. As a chiral molecule, it exists in two enantiomers, (R) and (S), with the (S) variant being the focus here. It is widely recognized for its utility as a chiral auxiliary in asymmetric synthesis, a ligand in organometallic chemistry, and a building block in the creation of pharmaceuticals and fine chemicals. Furthermore, it serves as a chiral resolving agent and plays a role in asymmetric catalysis, solidifying its importance in the field of organic chemistry.
Uses
Used in Asymmetric Synthesis:
(S)-4-Benzyl-2-methyl-2-oxazoline is utilized as a chiral auxiliary, a crucial component in enhancing the selectivity of reactions involving the formation of chiral molecules. Its application in this field is significant for producing enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals.
Used in Organometallic Chemistry:
In organometallic chemistry, (S)-4-Benzyl-2-methyl-2-oxazoline acts as a ligand, bonding with metal atoms to form complexes that can catalyze a range of chemical reactions. Its use in this area is vital for the development of new catalysts and the advancement of synthetic methods.
Used in Pharmaceutical Synthesis:
(S)-4-BENZYL-2-METHYL-2-OXAZOLINE serves as a building block in the synthesis of various pharmaceuticals and other fine chemicals. Its incorporation into the structure of these compounds can influence their biological activity, making it a valuable asset in drug discovery and development.
Used in Chiral Resolving:
(S)-4-Benzyl-2-methyl-2-oxazoline is employed as a chiral resolving agent, facilitating the separation of enantiomers, which is critical in the production of single-enantiomer drugs. The distinct properties of each enantiomer can lead to different effects in biological systems, making the ability to separate them a crucial aspect of pharmaceutical development.
Used in Asymmetric Catalysis:
As a participant in asymmetric catalysis, (S)-4-Benzyl-2-methyl-2-oxazoline contributes to the development of more efficient and selective catalysts. This application is essential for enhancing the yield and selectivity of chemical reactions, particularly in the synthesis of complex molecules like pharmaceuticals and agrochemicals.
Check Digit Verification of cas no
The CAS Registry Mumber 75866-72-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,8,6 and 6 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 75866-72:
(7*7)+(6*5)+(5*8)+(4*6)+(3*6)+(2*7)+(1*2)=177
177 % 10 = 7
So 75866-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO/c1-9-12-11(8-13-9)7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3/t11-/m0/s1
75866-72-7Relevant articles and documents
Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand
Wang, Hao,Bai, Zibo,Jiao, Tangqian,Deng, Zhiqiang,Tong, Huarong,He, Gang,Peng, Qian,Chen, Gong
supporting information, p. 3542 - 3546 (2018/03/21)
A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.
Synthesis and structural characterization of enantiopure exo and endo six-membered oxazoline-derived palladacycles
Mawo, Relindis Y.,Johnson, Diane M.,Wood, Jessica L.,Smoliakova, Irina P.
, p. 33 - 45 (2008/03/14)
Direct palladation of (S)-4-benzyl-2-methyl-2-oxazoline (1) and (S)-2-benzyl-4-tert-butyl-2-oxazoline (2) using Pd(OAc)2 in MeCN afforded the corresponding μ-acetato-dimeric complexes with six-membered exo and endo palladacycles, respectively. The same complexes were obtained by reacting coordination complexes Pd(1)2(OAc)2 and Pd(2)2(OAc)2 with Pd(OAc)2 in MeCN. Metalation of (S)-2,4-dibenzyl-2-oxazoline (3) with Pd(OAc)2 in AcOH, MeCN or CH2Cl2 resulted in the regiospecific formation of the six-membered endo palladacycle. The obtained μ-acetato-dimeric complexes were converted to the corresponding μ-chloro-dimeric derivatives 7, 11 and 13 by treatment with LiCl in acetone. The mononuclear PPh3 adducts 8, 12 and 14 were obtained by reacting dimers 7, 11 and 13 with PPh3 in benzene. NMR spectroscopy data supported the proposed structures of all complexes and suggested that exo and endo palladacycles in 8 and 12 have rigid boat conformations in CHCl3. The X-ray crystal structures of the μ-acetato dimer 6 with the exo palladacycle and the PPh3 adduct 14 with the endo metalacycle revealed boat conformation of both palladacycles and chiral twisted conformations δ(S) and λ(S), respectively, of the oxazoline rings in the solid state.
An Efficient and Versatile Method for the Synthesis of Optically Active 2-Oxazolines: An Acid-catalyzed Condensation of Ortho Esters with Amino Alcohols
Kamata, Kazuyuki,Agata, Isao,Meyers, A. I.
, p. 3113 - 3116 (2007/10/03)
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