66487-97-6

Basic information

• Product Name: 2-Furanmethanol, a-(phenylmethyl)-
• CAS NO: 66487-97-6
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• Mol File: 66487-97-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-Furanmethanol, a-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanmethanol, a-(phenylmethyl)-(66487-97-6)
• EPA Substance Registry System: 2-Furanmethanol, a-(phenylmethyl)-(66487-97-6)

Safety Data

• Hazardous Substances Data: 66487-97-6(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 87100-28-5 pinacol benzylboronate 
• 31593-52-9 2-benzyl-1,3-dithiane 
• 770-09-2 benzyltrimethylsilane 
• 40861-56-1 2-(2-furyl)-2-(trimethylsilyloxy)acetonitrile 
• 86607-65-0 1-(furan-2-yl)-2-phenylethanone 
• 110-00-9 furan 
• 122-78-1 phenylacetaldehyde 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 74425-89-1 2-benzyl-6-hydroxy-2H-pyran-3(6H)-one 
• 902151-17-1 benzyl (1-(furan-2-yl)-2-phenylethyl)carbamate 
• 914924-26-8 C₂₆H₂₂N₂O₇S 
• 13122-67-3 6-phenyl-4-oxohexanoic acid 

Relevant articles and documents

SUMO INHIBITOR COMPOUNDS AND USES THEREOF

There are disclosed, inter alia, methods of inhibiting an E1 enzyme, and compounds useful for inhibiting an E1 enzyme.

Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair

Highly enantioselective bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary alcohols in high yields with excellent enantioselectivities (up to 95% ee). The isolation of an α-silylcarbinol intermediate as well as DFT calculations revealed that the 1,2-anionotropic rearrangement occurred via a bisguanidinium silicate ion pair, which is the stereodetermining step. The chiral center formed is then retained without inversion through the subsequent [1,2]-Brook rearrangement. Crotyl acylsilanes were smoothly transformed into homoallylic linear crotyl alcohols with retention of E/Z geometry, and no branched alcohols were detected. This clearly suggested that the 1,2-anionotropic rearrangement occurred through a three-membered instead of a five-membered transition state.

Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes

The use of Me3SiO-/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.