705943-29-9

Basic information

• Product Name: 2-Cyclopenten-1-ol,4-(4-methoxyphenyl)-,(1R,4S)-rel-(9CI)
• Synonyms: 2-Cyclopenten-1-ol,4-(4-methoxyphenyl)-,(1R,4S)-rel-(9CI)
• CAS NO: 705943-29-9
• Molecular Formula: C12H14O2
• Molecular Weight: 190.23836
• Product Categories: METHOXY
• Mol File: 705943-29-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Cyclopenten-1-ol,4-(4-methoxyphenyl)-,(1R,4S)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopenten-1-ol,4-(4-methoxyphenyl)-,(1R,4S)-rel-(9CI)(705943-29-9)
• EPA Substance Registry System: 2-Cyclopenten-1-ol,4-(4-methoxyphenyl)-,(1R,4S)-rel-(9CI)(705943-29-9)

Safety Data

• Hazardous Substances Data: 705943-29-9(Hazardous Substances Data)

Upstream product

• 61740-26-9 cis-3-acetoxy-5-hydroxycyclopent-1-ene 
• 215877-38-6 4,5-dimethyl-2-(4-methoxyphenyl)-1,3,2-dioxaborolane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 188637-54-9 cyclopent-4-ene-1,3-diyl diethyl dicarbonate 
• 60895-01-4 3(S)-acetoxy-5-(R)-hydroxy-cyclopent-1-ene 
• 699-19-4 4-methoxyphenylmagnesium chloride 
• 14320-38-8 cyclopent-3-enol 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 

Downstream Products

• 1325231-59-1 (1S,3R)-3-(4-methoxyphenyl)cyclopentanol 

Relevant articles and documents

Intermolecular Noncovalent Hydroxy-Directed Enantioselective Heck Desymmetrization of Cyclopentenol: Computationally Driven Synthesis of Highly Functionalized cis-4-Arylcyclopentenol Scaffolds

New computationally driven protocols for the Heck desymmetrization of 3-cyclopenten-1-ol with aryldiazonium tetrafluoroborates were developed. These new conditions furnished remarkable product selectivity originating from a resident hydroxyl group and the critical choice of the reaction solvent. Mechanistic insights gleaned from theoretical calculations of the putative transition states predicted toluene as an adequate solvent choice to attain high enantioselectivity by strengthening the noncovalent interaction of the substrate hydroxyl group and the chiral cationic palladium catalyst. Laboratory experiments validated the theoretical predictions, and by employing 2% MeOH/toluene as solvent, the Heck-Matsuda reaction provided exclusively the cis-4-arylcyclopentenols 3a-l in good to excellent yields in enantiomeric excesses up to 99%. The performance of the new PyOx ligand (S)-4-tert-butyl-2-(3,5-dichloropyridin-2-yl)-4,5-dihydrooxazole was also successfully evaluated in the Heck-Matsuda desymmetrization of 3-cyclopenten-1-ol. The synthetic potential of these highly functionalized cis-4-arylcyclopentenols is illustrated by a gold-catalyzed synthesis of cyclopenta[b]benzofuran skeletons.

Rhodium-catalyzed asymmetric allylic substitution with boronic acid nucleophiles

An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH]2 and Xyl-P-PHOS al

Palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with Grignard reagents producing hitherto unreachable cis-1,2-isomers

Reaction of 4-cyclopentene-1,3-diol monoacetate with RMgCl (R = alkyl, aryl) in the presence of a palladium catalyst proceeded with retention of configuration to give cis-1,2-regio-isomers as the major products.