65878-53-7

Basic information

• Product Name: Cyclopropanecarboxylic acid, 1-amino-2-ethyl-, (1R,2S)- (9CI)
• Synonyms: Cyclopropanecarboxylic acid, 1-amino-2-ethyl-, (1R,2S)- (9CI);(1R,2S)-1-amino-2-ethylcyclopropanecarboxylic acid
• CAS NO: 65878-53-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.15704
• Product Categories: AMINOACID
• Mol File: 65878-53-7.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 238.1±23.0 °C(Predicted)
• Appearance: /
• Density: 1.184±0.06 g/cm3(Predicted)
• PKA: 2.99±0.50(Predicted)
• CAS DataBase Reference: Cyclopropanecarboxylic acid, 1-amino-2-ethyl-, (1R,2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 1-amino-2-ethyl-, (1R,2S)- (9CI)(65878-53-7)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 1-amino-2-ethyl-, (1R,2S)- (9CI)(65878-53-7)

Safety Data

• Hazardous Substances Data: 65878-53-7(Hazardous Substances Data)

Upstream product

• 97935-34-7 Potassium; (1R,2S)-2-ethyl-1-methoxycarbonyl-cyclopropanecarboxylate 
• 97935-31-4 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester 
• 18795-92-1 1,1-dimethyl 2-ethylcyclopropane-1,1-dicarboxylate 
• 87429-74-1 3-Azido-4-ethyl-4,5-dihydro-3H-pyrazole-3-carboxylic acid methyl ester 
• 81852-62-2 Methyl (Z)-2-azido-pentenoate 
• 87429-76-3 1-Azido-2-ethyl-cyclopropanecarboxylic acid 
• 98189-21-0 (1R,2S)-1-((S)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 145038-64-8 6-tert-butoxycarbonyl-(7aS)-3a,6-diazaperhydroindane-4,7-dione-5-spiro-1'-<(1'S,2'S)-2'-ethylcyclopropane> 
• 138457-96-2 Methyl (1R,2S)-(+)-1-Amino-2-ethyl-1-cyclopropanecarboxylate 
• 88950-66-7 (1RS,2SR)-1-[(tert-butoxycarbonyl)amino]-2-ethylcyclopropane-1-carboxylic acid 
• 138457-95-1 (1S,2S)-1-Amino-2-ethyl-cyclopropanecarboxylic acid methyl ester 

Downstream Products

• 65878-52-6 (+)-(1S,2R)-allocoronamic acid 
• 98189-21-0 (1R,2S)-1-((S)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 98244-44-1 (1S,2R)-1-((R)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 98244-40-7 (1S,2R)-1-((S)-2-Ethoxycarbonyloxy-2-phenyl-acetylamino)-2-ethyl-cyclopropanecarboxylic acid methyl ester 
• 106-98-9 1-butylene 

Relevant articles and documents

Titanium-mediated diastereoselective formation of (E)- or (Z)-2-substituted 1-vinylcyclopropanols: Scope and limitation, applications

Titanium-mediated cyclopropanation of α,β-unsaturated esters failed to provide 1-vinylcyclopropanol derivatives in useful yields, but (E)-2-substituted-1-vinylcyclopropanols were formed diastereoselectively from O-protected β-oxo- and β-halo esters, with the allylic double bond being created subsequently (Knoevenagel condensation or dehydrohalogenation). Titanium-mediated cyclopropanation of homoallyl alk-2-enoates, on the other hand, directly provided the corresponding Z diastereomers. Palladium(0)-catalysed azidation of their sulfonic esters (tosylate, mesylate), azide reduction, and subsequent double bond cleavage afforded (E)- or (Z)-2-alkyl-2,3-methanoamino acids, although improvements are required to perform the total asymmetric syntheses of molecules with three membered-rings by these methods. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids

One-pot palladium(0)-catalyzed alkylation and S(N') cyclization of 1,4- dichlorobut-2-ene 1 by the anion of α-substituted carbonitriles 2a-d can provide highly functionalized cyclopropanes (E)-4a-d, diastereoselectivity, (de 88-100%). Several attempts to achieve the asymmetric synthesis of the 1- amino-2-ethenylcyclopropanecarbonitrile (E)-9, by means of this new procedure, i.e., using chiral palladium ligands, chiral aminoacetonitriles (- )- and (+)-12 (from 1-hydroxypinanone) or chiral allyl chlorides (4S)-20b-d and (4R)-20e (from (2S) ethyl lactate) have pointed up the reversibility of the palladium-catalyzed cyclization step, responsible for the low enantioselectivity observed (ee ≤ 32%) and for the formation of byproducts, i.e., azepine derivatives 8a,b arising from subsequent aza Cope ring expansion. Molecular mechanics calculations using a modified MM2 type force field adapted to the π-allyl palladium complexes have explained these results. However, When performed under the Mitsunobu reaction conditions (DEAD, PMe3), therefore, in the absence of palladium catalyst, the S(N'), cyclization occurred also diastereoselectively (de > 88%) and provided the enantiomerically enriched 1-amino-2-propenylcyclopropanecarbonitrile (E)-22 (ee > 83%) suitable precursor of (1S,2S)-2,3-methanoamino acids.

Practical Stereoselective Syntheses of All Four Stereoisomers of Coronamic Acid (2-Ethyl-1-aminocyclopropane-1-carboxylic acid)

All four stereoisomers of coronamic acid were synthesized from both enantiomers of 1,2-butanediol.Cyclopropanation of cyclic sulfate with the dibenzyl malonate anion gave cyclopropane dibenbzyl ester in a quantitative yield.Transformation into a protected amino acid was acieved by stereoselective hydrolysis and Curtius rearrangement as the key step.Saponification and subsequent acidic hydrolysis in one pot and ion exchange gave a free amino acid in a high yield.