87601-24-9

Basic information

• Product Name: Oxazolidine, 2,2-dimethyl-5-phenyl-
• Synonyms: Oxazolidine, 2,2-dimethyl-5-phenyl-
• CAS NO: 87601-24-9
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Mol File: 87601-24-9.mol

Chemical Properties

• Boiling Point: 269°C at 760 mmHg
• Flash Point: 106.7°C
• Appearance: /
• Density: 0.993g/cm³
• Vapor Pressure: 0.00743mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: Oxazolidine, 2,2-dimethyl-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxazolidine, 2,2-dimethyl-5-phenyl-(87601-24-9)
• EPA Substance Registry System: Oxazolidine, 2,2-dimethyl-5-phenyl-(87601-24-9)

Safety Data

• Hazardous Substances Data: 87601-24-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15NO/c1-11(2)12-8-10(13-11)9-6-4-3-5-7-9/h3-7,10,12H,8H2,1-2H3

Upstream product

• 67-64-1 acetone 
• 7568-93-6 2-Amino-1-phenylethanol 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 532-27-4 1-chloroacetophenone 
• 124718-87-2 2-azido-1-phenylethan-1-ol 

Downstream Products

• 60980-03-2 2,2-dimethyl-3-dichloroacetyl-5-phenyl-1,3-oxazolidine 

Relevant articles and documents

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

A convenient one-pot synthesis and bioactivity of N-dichloroacetyl-5-aryl- 1,3-oxazolidines

New N-dichloroacetyl-5-aryl-1,3-oxazolidines 4 were synthesized by cycloaddition reaction of an aryl substituted hydroxyalkylamine 1 with aldehyde or ketone 2, followed by acylation, without isolation of the intermediate product 3. The structures of compounds 4 were determined by spectral and elemental analyses. The structure of 4b was determined by an X-ray crystallographic analysis. The bioassay results demonstrate that these compounds could alleviate chlorsulfuron injury to maize.

Preparation of 3-dihaloacetyl oxazolidines

The disclosure herein relates to a new process for the preparation of 3-dihaloacetyl (un)substituted oxazolidine compounds by the catalytic hydrogenation of nitroalcohols with aldehydes or ketones followed by reaction with a dihaloacetyl halide.