21917-20-4

Usage

Type of compound

Dicarboxylic acid ester

Structure

Cyclopentane ring with carboxylic acid groups on the 1 and 2 positions

Applications

Building block in organic synthesis for pharmaceuticals, agrochemicals, and materials; potential chiral ligand in asymmetric catalysis

Physical state

White to off-white solid at room temperature

Melting point

Around 90-95°C

Hazard classification

Non-hazardous material

Safety precautions

Handle and use in accordance with good laboratory practices to avoid potential risks

InChI:InChI=1/C7H10O4/c8-6(9)4-2-1-3-5(4)7(10)11/h4-5H,1-3H2,(H,8,9)(H,10,11)/p-2

Upstream product

• 80656-14-0 trans-1,2-cyclopentanedicarboxylic acid 
• 80656-13-9 trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester 
• 96055-59-3 (-)-dimenthyl (1S,2S)-cyclopentane-1,2-dicarboxylate 
• 88315-64-4 (1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid 
• 136412-63-0 (1S,2S)-2-((1S,2R,3S)-1,2,3,4-Tetrahydroxy-butyl)-cyclopentanecarboxylic acid methyl ester 
• 80657-42-7 (3aS,4R,5S,7aR)-5-Isopropyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 80595-64-8 (3aS,4S,7aR)-2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 80595-64-8 2,3,3a,4,5,7a-Hexahydro-1H-indene-4-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 80595-54-6 4β-(((o-nitrophenyl)selenyl)methyl)-5β-(2-propyl)-2,3,3aβ,4,5,7aα-hexahydroindene 
• 80656-11-7 4β-(((o-nitrophenyl)selenyl)methyl)-2,3,3aβ,4,5,7aα-hexahydroindene 
• 80656-15-1 4β-(hydroxymethyl)-5β-(2-propyl)-2,3,3aβ,4,5,7aα-hexahydroindene 
• 80656-17-3 4-methylene-5β-(2-propyl)-2,3,3aβ,4,5,7aα-hexahydroindene 
• 80595-52-4 4-methylene-2,3,3aβ,4,5,7aα-hexahydroindene 
• 80595-50-2 4β-(hydroxymethyl)-2,3,3aβ,4,5,7aα-hexahydroindene 

Downstream Products

• 4841-91-2 dimethyl cis-1,2-cyclopentanedicarboxylate 
• 80656-13-9 trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester 
• 70774-29-7 trans-1,2-bis(hydroxymethyl)cyclopentane 
• 3145-88-8 Cyclopentan-1.2-trans-diamin 
• 35878-28-5 cyclopentane-cis-1,2-dicarboxylic acid anhydride 
• 5763-49-5 2,4,5,6,3a,6a-hexahydro-2-oxapentalen-1,3-dione 
• 501666-10-0 (1S,2S)-Cyclopentane-1,2-dicarbonyl dichloride 

Relevant academic research and scientific papers

Synthesis of optically pure di- to tetra-substituted cyclopentanes from sugar-derived norbornene derivatives

The chiral norbornene derivative 2 obtained from Lewis acid-catalyzed reaction of an L-arabinose-derived dienophile 1 and cyclopentadiene was oxidized with OsO4-NaIO4 to the dialdehyde 3, a tetrasubstituted cyclopentane. Mild treatment of 3 with [Rh(dppp)2]Cl [dppp = Ph2P(CH2)3PPh2] (4) selectively epimerized the aldehyde adjacent to the methoxycarbonyl group to give the epi-aldehyde 8. Under more vigorous conditions, this group was decarbonylated to give the monoaldehyde 11, and more strenuous treatment removed the second aldehyde group to give the didecarbonylated cyclopentane derivative 5. The structure and optical purity of 5 was confirmed by its transformation into (1S,2S)-cyclopentane-1,2-dicarboxylic acid (7). The chiral norbornene derivative 2 obtained from Lewis acid-catalyzed reaction of an L-arabinose-derived dienophile 1 and cyclopentadiene was oxidized with OsO4-NaIO4 to the dialdehyde 3, a tetrasubstituted cyclopentane. Mild treatment of 3 with [Rh(dppp)2]Cl [dppp = Ph2P(CH2)3PPh2] (4) selectively epimerized the aldehyde adjacent to the methoxycarbonyl group to give the epi-aldehyde 8. Under more vigorous conditions, this group was decarbonylated to give the monoaldehyde 11, and more strenuous treatment removed the second aldehyde group to give the didecarbonylated cyclopentane derivative 5. The structure and optical purity of 5 was confirmed by its transformation into (1S,2S)-cyclopentane-1,2-dicarboxylic acid (7).

Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis

Novel C2- and C1-symmetric chiral bisoxazolines with a cyclic backbone have been synthesized in an asymmetric manner starting from meso anhydrides. All synthetic steps are easy to perform and lead to the desired products in good over

A cyclopentane conformational restraint for a peptide nucleic acid: Design, asymmetric synthesis, and improved binding affinity to DNA and RNA

(Matrix presented) A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding prop

Synthesis and First Applications of a New Chiral Auxiliary (tert-Butyl 2-(tert-Butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate)

Both enantiomers of tert-butyl 2(tert-butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate (11; Bbdmoic) were prepared from L-alanine (Schemes 1 and 2).The parent heterocycle, 2-tert-butyl-5,5-dimethylimidazolidin-4-one (12; from 2-aminoisobutyramide, H-A