132836-66-9

Basic information

• Product Name: (N-ACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE
• Synonyms: (4R)-3-ACETYL-4-BENZYL-1,3-OXAZOLIDIN-2-ONE;(4S)-3-ACETYL-4-BENZYL-1,3-OXAZOLIDIN-2-ONE;(4S)-3-ACETYL-4-(PHENYLMETHYL)-2-OXAZOLIDINONE;TIMTEC-BB SBB010012;(S)-(+)-3-ACETYL-4-BENZYL-2-OXAZOLIDINONE;(S)-3-ACETYL-4-BENZYL-2-OXAZOLIDINONE;(R)-(-)-3-ACETYL-4-BENZYL-2-OXAZOLIDINONE;(N-ACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE
• CAS NO: 132836-66-9
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Product Categories: Oxazolidinone;Peptide;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 132836-66-9.mol

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 360.05°C (rough estimate)
• Flash Point: 187.117 °C
• Appearance: off white crystals
• Density: 1.1825 (rough estimate)
• Vapor Pressure: 3.71E-06mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.27±0.40(Predicted)
• CAS DataBase Reference: (N-ACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (N-ACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE(132836-66-9)
• EPA Substance Registry System: (N-ACETYL)-(4R)-BENZYL-2-OXAZOLIDINONE(132836-66-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 132836-66-9(Hazardous Substances Data)

Usage

Chemical Properties

offwhite crystals

InChI:InChI=1/C12H13NO3/c1-9(14)13-11(8-16-12(13)15)7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3/t11-/m1/s1

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 533-58-4 2-Iodophenol 
• 660866-51-3 (S)-4-benzyl-3-ethynyl-1,3-oxazolidin-2-one 

Downstream Products

• 141733-98-4 (4S,3'S)-3-<3-(3-Benzyloxy-4-methoxyphenyl)-4-nitrobutyryl>4-benzyl-2-oxazolidinon 
• 141733-97-3 (4S,3'R)-3-<3-(3-Benzyloxy-4-methoxyphenyl)-4-nitrobutyryl>4-benzyl-2-oxazolidinon 
• 221044-37-7 (S)-4-Benzyl-3-((E)-4,4-dimethyl-pent-2-enoyl)-oxazolidin-2-one 
• 391277-76-2 (S)-4-Benzyl-3-(3-hydroxy-pent-4-enoyl)-oxazolidin-2-one 
• 494803-05-3 (3'S,4S)-4-benzyl-3-[3'-hydroxy-3'-(4-nitrophenyl)propionyl]oxazolidin-2-one 
• 502765-46-0 (S)-4-Benzyl-3-[(S)-3-hydroxy-2-((S)-hydroxy-phenyl-methyl)-3-phenyl-propionyl]-oxazolidin-2-one 

Relevant articles and documents

Enantioselective multicomponent synthesis of fused 6-5 bicyclic 2-butenolides by a cascade heterobicyclisation process

The successive coupling of an alkoxy(aryl/heteroaryl)carbene complex of chromium with either a ketone or an imide lithium enolate and then a 3-substituted (H, TMS, PhCH2, PhCH2CH2, Me) propargylic organomagnesium reagent h

Formation of chiral tertiary homoallylic alcohols via Evans aldol reaction or enzymatic resolution and their influence on the Sharpless asymmetric dihydroxylation

Enantioenriched tertiary homoallylic alcohol derivatives (S)-2c and (S)-2a were obtained via Evans aldol methodology and enzymatic resolution of racemic tertiary acetate 2e, respectively. In order to study asymmetric 1,3-induction of the stereogenic cente

Application of ynamides in the synthesis of 2-amidoindoles

A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-iodoanilines is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without acti

Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

Electrogenerated base-induced N-acylation of chiral oxazolidin-2-ones. 2

An improved and efficient electrochemical N-acylation of chiral oxazolidin-2-ones has been achieved. The generation of the nitrogen anion is obtained under mild conditions and without addition of base or probase, by direct electrolysis of a solution of Me

3-phenylpyrrolidine alpha-1 adrenergic compounds

Compounds having the formula are alpha 1 adrenoreceptor antagonists. Processes for making these compounds, synthetic intermediates employed in these processes and a method for inhibiting alpha 1 adrenoreceptors and treating benign prostatic hyperplasia (also called benign prostatic hypertrophy or BPH) and other urological diseases such as BOO (bladder outlet obstruction), neurogenic bladder and gynecological syndromes such as dysmenorrhea are disclosed.

Simple and efficient N-acylation reactions of chiral oxazolidinone auxiliaries

A simplified procedure for the N-acylation of oxazolidin-2-one chiral auxiliaries has been developed. The acylations occur at room temperature in the presence of triethylamine and catalytic quantities of 4-(N,N-dimethylamino)pyridine, thereby eliminating the necessity for a strong base such as butyllithium. Acylations with both symmetrical and mixed anhydrides, as well as acid chlorides, occur with a wide variety of oxazolidinone auxiliaries.

Biosynthesis of Tetronasin: Part 3. Preparation of Deuterium Labelled Tri- and Tetraketides as Putative Biosynthetic Precursors of Tetronasin

The preparation of seven deuterium labelled N-acetyl cysteamine thioesters (2a), (2b), (3a), (3b), (4), (5) and (6) as putative biosynthetic precursors of the acyl tetronic acid ionophore tetronasin is described.