181369-36-8

Basic information

• Product Name: 2H-Azirine-2-carboxylicacid,3-methyl-,1,1-dimethylethylester,(R)-(9CI)
• Synonyms: 2H-Azirine-2-carboxylicacid,3-methyl-,1,1-dimethylethylester,(R)-(9CI)
• CAS NO: 181369-36-8
• Molecular Formula: C8H13NO2
• Molecular Weight: 0
• Product Categories: CARBOXYLICESTER;GLYCINESCAFFOLD
• Mol File: 181369-36-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Azirine-2-carboxylicacid,3-methyl-,1,1-dimethylethylester,(R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Azirine-2-carboxylicacid,3-methyl-,1,1-dimethylethylester,(R)-(9CI)(181369-36-8)
• EPA Substance Registry System: 2H-Azirine-2-carboxylicacid,3-methyl-,1,1-dimethylethylester,(R)-(9CI)(181369-36-8)

Safety Data

• Hazardous Substances Data: 181369-36-8(Hazardous Substances Data)

Usage

Class

Azirine carboxylic acid ester

Physical State

Colorless liquid

Molecular Weight

143.18 g/mol

Use

Reagent for the preparation of nitrogen-containing compounds and pharmaceuticals

Biological Activity

Potential biological activity and selectivity in drug development

Upstream product

• 181369-25-5 C₁₅H₂₁NO₅S 
• 1694-31-1 tert-butyl acetoacetate 
• 101798-63-4 t-Butyl oximinoacetoacetate 
• 937375-79-6 (+)-tert-butyl (2S,3R)-3-methylaziridine-2-carboxylate 
• 937375-78-5 tert-butyl (R)-1-(naphthalen-2-ylthio)propan-2-ylcarbamate 
• 4248-19-5 tert-butyl carbazate 
• 129319-91-1 (R)-(-)-N-(tert-Butoxycarbonyl)-2-methylaziridine 
• 167938-56-9 tert-butyl [(2S)-2-hydroxypropyl]carbamate 
• 1394979-17-9 (-)-tert-butyl (2S,3R)-1-benzyl-3-methylaziridine-2-carboxylate 

Relevant articles and documents

Synthesis of Highly Substituted Azepanones from 2 H-Azirines by a Stepwise Annulation/Ring-Opening Sequence

Bicyclic aziridines possessing a 1-azabicyclo[4.1.0]heptan-2-one core were prepared from 2H-azirines by a stepwise annulation sequence involving a diastereoselective allylindanation, an N-acylation, and a ring-closing metathesis to construct the six-membe

Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines

A regioselective synthetic method for the preparation of indolopyrazines was demonstrated through a sequential Rh-catalyzed formal [3+3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint.

RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles

RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

General entry to asymmetric one-pot [ N + 2 + n ] cyclization for the synthesis of three- to seven-membered azacycloalkanes

Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolat

Lithiation-induced migrations from nitrogen to carbon in terminal aziridines

(Chemical Equation Presented) Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valua

Dimerization and isomerization reactions of α-lithiated terminal aziridines

(Chemical Equation Presented) The scope of dimerization and isomerization reactions of α-lithiated terminal aziridines is detailed. Regio-and stereoselective deprotonation of simple terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide (LTMP) or lithium dicyclohexylamide (LiNCy 2) generates trans-α-lithiated terminal aziridines. These latter species can then undergo dimerization or isomerization reactions depending on the nature of the N-protecting group. α-Lithiated terminal aziridines bearing N-alkoxycarbonyl (Boc) protection undergo N- to C-[1,2] migration to give N-H trans-aziridinylesters. In contrast, aziridines bearing N-organosulfonyl [tert-butylsulfonyl (Bus)] protection undergo rapid dimerization to give 2-ene-1,4-diamines or, if a pendant alkene is present, diastereoselective cyclopropanation to give 2-aminobicyclo[3.1.0]hexanes. All of these reactions were used as key steps in the preparation of synthetically and biologically important targets.

Lipase-catalyzed resolution of (2R*,3S*)- and (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol at low temperatures and determination of the absolute configurations of the four stereoisomers

(Chemical Equation Presented) Lipase-catalyzed resolution of (2R*,3S*)-3-methyl-3-phenyl-2-aziridinemethanol, (±)-2, at low temperatures gave synthetically useful (2R,3S)-2 and its acetate (2S,3R)-2a with (2S)-selectivity (E = 55 at -40 °C), while a simil