36866-68-9

Basic information

• Product Name: 3-Phenyltetrahydrofuran-2-ol
• Synonyms: 3-Phenyltetrahydrofuran-2-ol
• CAS NO: 36866-68-9
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• Mol File: 36866-68-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 135 °C(Press: 2 Torr)
• Appearance: /
• Density: 1.165±0.06 g/cm3(Predicted)
• PKA: 12.94±0.40(Predicted)
• CAS DataBase Reference: 3-Phenyltetrahydrofuran-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyltetrahydrofuran-2-ol(36866-68-9)
• EPA Substance Registry System: 3-Phenyltetrahydrofuran-2-ol(36866-68-9)

Safety Data

• Hazardous Substances Data: 36866-68-9(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 104-54-1 3-Phenylpropenol 
• 6836-98-2 3-phenyldihydrofuran-2-one 
• 66661-72-1 ethyl 4-oxo-2-phenylbutanoate 
• 22927-17-9 4-hydroxy-4-phenyl-butyraldehyde 

Downstream Products

• 1376348-28-5 (E)-ethyl 6-bromo-4-phenylhex-2-enoate 
• 22927-23-7 4-phenyl-2,3-dihydrofuran 
• 80816-30-4 3-phenyl-4-pentenol 

Relevant articles and documents

Formal [4 + 1]- and [5 + 1]-annulation by an SN2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles

K2CO3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate a

An interrupted fischer indolization approach toward fused indoline-containing natural products

An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products by way of an interrupted Fischer indolization sequence. Our studies show that the approach will likely be amenable to the synthesis of complex targets, such as the communesin natural products.

Stereoselective Substitution at Phenyl-Substituted γ-Lactols with Organometallic Compounds

A variety of monosubstituted γ-lactols 4-6 were prepared in good yields by DIBAL reduction of the corresponding γ-lactones 1-3.The monophenyl-substituted lactols 4b-6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles.The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ-lactols.For the reaction of the 3- and 4-substituted derivatives 4b and 5b, respectively, good to excellent trans selectivity was observed, while the 5-substituted derivative reacted without any diastereoselectivity.These results were interpreted by means of the Felkin-Anh model. - Keywords: γ-Lactone / Reduction / γ-Lactol / Lewis acid / Tetrahydrofurans