20047-22-7

Basic information

• Product Name: (E)-4-(4-chlorophenyl)but-3-en-1-ol
• Synonyms: (E)-4-(4-chlorophenyl)but-3-en-1-ol
• CAS NO: 20047-22-7
• Molecular Weight: 182.65
• Mol File: 20047-22-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (E)-4-(4-chlorophenyl)but-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(4-chlorophenyl)but-3-en-1-ol(20047-22-7)
• EPA Substance Registry System: (E)-4-(4-chlorophenyl)but-3-en-1-ol(20047-22-7)

Safety Data

• Hazardous Substances Data: 20047-22-7(Hazardous Substances Data)

Upstream product

• 6640-25-1 4-chlorophenyl cyclopropyl ketone 
• 104-88-1 4-chlorobenzaldehyde 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 
• 18228-43-8 (±)-(4-chlorophenyl)(cyclopropyl)methanol 
• 827605-29-8 2-(4-chloro-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 
• 930-22-3 epoxybutene 
• 1250907-72-2 methyl (E)-4-(4-chlorophenyl)but-3-enoate 
• 127404-70-0 (E)-4-(4-chlorophenyl)-3-butenoic acid 

Downstream Products

• 1426692-57-0 3-chloro-2-(4-chlorophenyl)tetrahydrofuran 
• 19967-22-7 4-(p-chlorophenyl)-1-butanol 

Relevant articles and documents

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols

Copper-catalyzed cross-coupling reactions of vinyl epoxide with arylboronates to obtain aryl-substituted homoallylic alcohols are described. The reaction selectivity was different to that of previously reported vinyl epoxide ring-opening reactions using aryl nucleophiles. The reaction proceeded under mild conditions, affording aryl-substituted homoallylic alcohols with high selectivity and in good to excellent yields. The reaction provides convenient access to aryl-substituted homoallylic alcohols from vinyl epoxide.

Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans

The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.