1000376-26-0

Basic information

• Product Name: (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene
• Synonyms: (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene
• CAS NO: 1000376-26-0
• Molecular Weight: 272.195
• Mol File: 1000376-26-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene(1000376-26-0)
• EPA Substance Registry System: (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene(1000376-26-0)

Safety Data

• Hazardous Substances Data: 1000376-26-0(Hazardous Substances Data)

Upstream product

• 129413-75-8 (E)-(5-bromopent-3-en-1-yl)benzene 
• 73183-34-3 bis(pinacol)diborane 
• 1027473-57-9 Methanesulfonic acid (E)-5-phenyl-pent-2-enyl ester 
• 791602-98-7 (E)-5-phenyl-2-penten-1-yl methyl carbonate 
• 126435-88-9 (E)-5-phenylpent-2-enyl benzoate 
• 126435-89-0 (E)-5-phenyl-2-penten-1-ol acetate 
• 1267551-55-2 1-nitro-3-((5-phenylpent-2-en-1-yl)oxy)benzene 
• 673-31-4 phenprobamate 
• 75927-49-0 pinacol vinylboronate 
• 1000376-19-1 (Z)-5-phenyl-2-penten-1-yl methyl carbonate 

Downstream Products

• 181229-59-4 (3R)-5-phenylpent-1-en-3-ol 
• 1428537-74-9 (1R,3Z)-1,6-diphenylhex-3-en-1-ol 
• 1428537-73-8 (1S,3E)-1,6-diphenylhex-3-en-1-ol 

Relevant articles and documents

Understanding Six-Membered NHC-Copper(I) Allylic Borylation Selectivity by Comparison with other Catalysts and Different Substrates

We recently introduced a family of 6-NHC-Cu(I) catalysts that exhibit highest selectivities (regio- and enantio-) exclusively when aryl ethers are used as the leaving group. Understanding the match between a catalyst and leaving group remains elusive. We

Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions

Allylic substitutions that afford α-substituted allylboronates bearing B-substituted tertiary or quaternary carbon stereogenic centers are presented. C-B bond-forming reactions, catalyzed by chiral bidentate Cu-NHC complexes, are performed in the presence of commercially available bis(pinacolato)diboron. Transformations proceed in high yield (up to >98%) and site selectivity (>98% SN2′), and in up to >99:1 enantiomer ratio. Trans- or cis-disubstituted alkenes can be used; alkyl- (linear as well as branched) and aryl-trisubstituted allylic carbonates serve as effective substrates. Allylboronates that bear a quaternary carbon center are air-stable and can be easily purified by silica gel chromatography; in contrast, secondary allylboronates cannot be purified in the same manner and are significantly less stable. Oxidation of the enantiomerically enriched products furnishes secondary or tertiary allylic alcohols, valuable small molecules that cannot be easily obtained in high enantiomeric purity by alternative synthesis or kinetic resolution approaches.

Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: An efficient route to optically active α-chiral allylboronates

A method for the synthesis of α-chiral allylboronates featuring the Cu(I)-catalyzed enantioselective substitution of readily available allylic carbonates with a diboron is described. Using this method, various α-chiral allylboronates, including functionalized allylboronates, were successfully synthesized, with high enantiomeric purity. Copyright