28973-89-9

Basic information

• Product Name: (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid
• Synonyms: (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid;1-.alpha.-Campholenic acid;3-Cyclopentene-1-acetic acid, 2,2,3-trimethyl-, (R)-;Campholenic acid, alpha;L-.alpha.-Campholenic acid;Nsc44160
• CAS NO: 28973-89-9
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 0
• Mol File: 28973-89-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid(28973-89-9)
• EPA Substance Registry System: (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid(28973-89-9)

Safety Data

• Hazardous Substances Data: 28973-89-9(Hazardous Substances Data)

Usage

Description

(R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid is a chiral chemical compound with the molecular formula C11H18O2. As a carboxylic acid, it features a carboxyl group (–COOH) and is distinguished by its unique cyclopentene ring structure, which endows it with specific chemical properties. The (R) configuration in its name signifies the presence of a non-superimposable mirror image, highlighting its importance in stereochemistry.

Uses

Used in Organic Synthesis:
(R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid is utilized as a key component in organic synthesis, where its distinct cyclopentene ring and carboxylic acid group contribute to the formation of various complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid serves as a precursor for the synthesis of different pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Research and Development:
(R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid is also employed in research and development within the pharmaceutical and chemical sectors. Its chiral nature and functional groups make it a valuable compound for exploring new reactions and creating novel molecules with specific biological activities.
Used in Chemical Industry:
(R)-2,2,3-Trimethyl-3-cyclopentene-1-acetic acid is further used in the chemical industry for the production of various specialty chemicals and materials, leveraging its unique structural features and reactivity.

Upstream product

• 23727-15-3 (S)-campholenic aldehyde 
• 33171-48-1 (1S,4R,6S)-6-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 14888-09-6 (-)-l-10-camphorsulfonic acid ammonium salt 
• 10293-06-8 (1R)-3-endo-bromocamphor 
• 4955-29-7 (-)-trans-pinocarvyl acetate 
• 1674-08-4 (-)-trans-pinocarveol 
• 118923-70-9 Pinocarveol-hydrobromid 
• 35963-20-3 (R)-10-camphorsulfonic acid 

Downstream Products

• 473-47-2 (+)-((1R,3Ξ)-2,2,3-trimethyl-cyclopentyl)-acetic acid 
• 52437-39-5 (R)-(+)-2-(2,2,3-trimethyl-cyclopent-3-en-1-yl)ethanol 
• 91175-73-4 (R)-(+)-ethyl (2,2,3-trimethyl-cyclopent-3-en-1-yl)acetate 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 952722-05-3 C₂₀H₂₈O₂ 
• 952722-06-4 C₂₀H₂₆O₂ 
• 91175-74-5 [2-(2,2,3-Trimethylcyclopent-3-enyl)ethyl]-p-toluensulfonat 
• 130740-85-1 ((R)-6,6-Dimethyl-5-oxo-cyclohex-3-enyl)-acetic acid methyl ester 
• 130740-87-3 ((R)-2,2,4-Trimethyl-3-oxo-cyclohexyl)-acetic acid 
• 130740-84-0 ((R)-2,2,4-Trimethyl-3-oxo-cyclohexyl)-acetic acid methyl ester 
• 130740-88-4 ((R)-2,2,4-Trimethyl-3-oxo-cyclohexyl)-thioacetic acid S-ethyl ester 
• 130740-86-2 ((R)-2,2-Dimethyl-3-oxo-cyclohexyl)-acetic acid methyl ester 
• 52486-39-2 (1R)-(-)-2,2,3-trimethylcyclopent-3-ene-1-ethyl acetate 
• 1182345-87-4 (+)-(1S)-4-methoxybenzyl (2,2,3-trimethylcyclopent-3-enyl)-methylcarbamate 

Relevant articles and documents

Enantioselective syntheses of diquinane and (cis, anti, cis)-linear triquinanes

The enantioselective syntheses of diquinane and cis, anti, cis-linear triquinanes, starting from the readily available (S)-campholenaldehyde, employing an intramolecular rhodium carbenoid CH insertion reaction, are described.

Synthetic approaches to neorogiolanes: enantiospecific synthesis of 12-methoxyneorogiola-1,3,5,7(17),8-pentaene

Enantiospecific synthesis of 12-methoxyneorogiola-1,3,5,7(17),8-pentaene, containing the complete carbon framework of the natural diquinane diterpenes neorogioldiols, starting from (S)-campholenaldehyde is described.

Thermal isomerization of isoborneols and dehydroisoborneols to new chiral building blocks in terpenoid synthesis

The substituted isoborneols 1a-1g and 5,6-dehydroisoborneols 6a-6c, readily prepared in excellent yields from (+)-camphor and (+)-5,6-dehydrocamphor (2) by aryl, vinyl, or alkyl Grignard addition in the presence of stoichiometric amounts of CeCl3, were thermally isomerized in a flow reactor system under DGPTI (dynamic gas-phase thermo-isomerization) conditions at temperatures between 480 and 630° to give the enantiomerically pure monocyclic carbonyl compounds 7a-7d, 19a,b, 23, and 24. In all cases, product formation proceeded highly regio- as well as stereoselectively. The absolute configurations of the new stereogenic centers were determined by 1H-NOE measurements. DGPTI of the aryl substrates 1a-1d is proposed to effect initial cleavage of the weakest single bond in the molecule under formation of a diradical intermediate state followed by intramolecular H-abstraction to afford the acetophenone derivatives 7a-7d. This reaction path was further supported by a 2H-labeling study showing the OH group to be the exclusive H-source. In contrast, DGPTI of the vinyl substrates 1e and 6b allowed concerted retro-ene and oxy-Cope rearrangements. In the case of 5,6-dehydro-2-phenylisoborneol (6a), concomitant diradical and retro-Diels-Alder reaction pathways could be observed. In addition, a new route to (+)-rrans-a-campholanic acid (9) and (+)-trans-a-dihydrocampholytic acid (14) is presented by regioselective Baeyer-Villiger oxidation and subsequent hydrolysis of 7c and 7d, respectively.