221158-94-7

Basic information

• Product Name: Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI)
• Synonyms: Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI);(1S,2R)-1-Amino-2-(methoxycarbonyl)cyclobutane;Methyl (1R,2S)-2-aminocyclobutane-1-carboxylate;(1S,2R)-Methyl 2-aMinocyclobutanecarboxylate;(1R,2S)-2-AMinocyclobutanecarboxylic acid Methyl ester hydrochloride;(1R,2S) 2-Aminocyclobutanecarboxylic acid methyl ester;methyl (1R,2S)-2-aminocyclobutane-1-carboxylate hydrochloride
• CAS NO: 221158-94-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.15704
• Product Categories: AMINEPRIMARY;AMINOACID
• Mol File: 221158-94-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 169.1±33.0 °C(Predicted)
• Appearance: /
• Density: 1.111±0.06 g/cm3(Predicted)
• PKA: 10.01±0.40(Predicted)
• CAS DataBase Reference: Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI)(221158-94-7)
• EPA Substance Registry System: Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI)(221158-94-7)

Safety Data

• Hazardous Substances Data: 221158-94-7(Hazardous Substances Data)

Usage

General Description

Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI) is a chemical compound commonly referred to as (1R,2S)-2-Aminocyclobutanecarboxylic acid methyl ester. It is a methyl ester derivative of cyclobutanecarboxylic acid, containing an amino group. Cyclobutanecarboxylic acid, 2-amino-, methyl ester, (1R,2S)- (9CI) is a chiral molecule, with two stereocenters, and exists in two enantiomeric forms. It is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals, as well as in research and development in the field of organic chemistry. Its chemical structure and properties make it a versatile and valuable compound for chemical and pharmaceutical industries.

Upstream product

• 2607-03-6 dimethyl cis-1,2-cyclobutanedicarboxylate 
• 88335-88-0 (1S,2R)-cis-2-methoxycarbonyl-cyclobutane-1-carboxylic acid 
• 868364-62-9 methyl (-)-(1R,2S)-2-[(tert-butyloxycarbonyl)amino]cyclobutanecarboxylate 
• 221158-91-4 methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate 
• 221158-92-5 methyl 2-azidocarbonyl-(1R,2S)-cyclobutane-1-carboxylate 

Downstream Products

• 517913-91-6 (1R,2S)-2-[((1R,2S)-2-Benzyloxycarbonylamino-cyclobutanecarbonyl)-amino]-cyclobutanecarboxylic acid methyl ester 

Relevant articles and documents

(+)- and (-)-2-aminocyclobutane-1-carboxylic acids and their incorporation into highly rigid β-peptides: Stereoselective synthesis and a structural study

Several derivatives of (+)- and (-)-2-aminocyclobutane-1-carboxylic acid, 1, have been prepared through enantiodivergent synthetic sequences. The stereoselective synthesis of free amino acid (+)-1 has been achieved, and this product has been fully charact

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide

Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane β-amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded β-amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-β-amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. Copyright (C) 2000 Elsevier Science Ltd.