167693-19-8

Basic information

• Product Name: 1,3,2-Dioxaborolane, 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-
• CAS NO: 167693-19-8
• Molecular Formula: C12H21BO2
• Mol File: 167693-19-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborolane, 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-(167693-19-8)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 2-(cyclopentylidenemethyl)-4,4,5,5-tetramethyl-(167693-19-8)

Safety Data

• Hazardous Substances Data: 167693-19-8(Hazardous Substances Data)

Usage

Type of compound

Boronic acid derivative

Structure

Cyclic compound containing a boron atom and a cyclopentylidene group

Organic synthesis

Formation of carbon-carbon and carbon-heteroatom bonds

Pharmaceutical industry

Building block for the synthesis of various drug compounds

Materials science

Building block in the production of organic electronic materials and polymers

Upstream product

• 60484-91-5 (cyclopentylidenemethoxy)trimethylsilane 
• 73183-34-3 bis(pinacol)diborane 
• 872-53-7 cyclopentanealdehyde 
• 120-92-3 cyclopentanone 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 2468-56-6 1-iodo-5-hexyne 
• 66977-99-9 6-bromo-1-hexyne 
• 1528-30-9 methylenecyclopentane 
• 72824-04-5 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane 

Relevant articles and documents

Alkenyl boron compound and preparation method and application thereof

The invention discloses an alkenyl boron compound and a preparation method and application thereof. The preparation method comprises the following steps: in a protective atmosphere, enabling a uniformly mixed reaction system containing a lithium enol reag

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates

An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.

Copper(I)-catalyzed regio- and stereoselective intramolecular alkylboration of propargyl ethers and amines

The copper(I)-catalyzed regio- and stereoselective intramolecular alkylation of propargyl ethers and amines bearing an alkyl electrophilic moiety has been developed. The reaction showed high functional group tolerance and gave highly functionalized alkenylboronates bearing heterocyclic rings, which are versatile synthetic intermediates in organic chemistry. The borylation products can be transformed into multisubstituted alkenes through stereospecific transformations. Mechanistic studies showed that the chemo- and stereoselectivity of copper(I)-catalyzed borylation depends on the type of leaving group. Density functional theory calculations suggested that the regioselectivity of the borylcupration of the alkyne is controlled by the electronic effect of the oxygen atom of the propargyl ether in combination with the steric congestion between the boryl group and the substituent at the propargylic position.