1380436-41-8

Basic information

• Product Name: (S)-2-(4’-methoxyphenyl)tetrahydrofuran
• Synonyms: (S)-2-(4’-methoxyphenyl)tetrahydrofuran
• CAS NO: 1380436-41-8
• Molecular Weight: 178.231
• Mol File: 1380436-41-8.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(4’-methoxyphenyl)tetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4’-methoxyphenyl)tetrahydrofuran(1380436-41-8)
• EPA Substance Registry System: (S)-2-(4’-methoxyphenyl)tetrahydrofuran(1380436-41-8)

Safety Data

• Hazardous Substances Data: 1380436-41-8(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 594847-89-9 (S)-1-(4’-methoxyphenyl)butan-1,4-diol 
• 79623-15-7 2-p-methoxyphenyltetrahydrofuran 

Relevant articles and documents

Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers

A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.

Cyclic ether synthesis from diols using trimethyl phosphate

Cyclic ethers have been effectively synthesized via the intramolecular cyclization of diols using trimethyl phosphate and NaH. The present cyclization could proceed at room temperature to produce 5-7 membered cyclic ethers in good to excellent yields. Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their stereochemistries.

Bronsted acid catalyzed asymmetric SN2-Type O-alkylations

Bridging the gap: Bronsted acids catalyze an intramolecular S N2-type alkylation of alcohols with ethers by bridging a pentacoordinate transition state, thus simultaneously activating both the leaving group and nucleophile (see scheme). Density functional calculations provide detailed insight into the course of the reaction and the transition-state structure.

Intramolecular displacement of phenylselenone by a hydroxy group: Stereoselective synthesis of 2-substituted tetrahydrofurans

An efficient and stereocontrolled synthesis of 2-substituted tetrahydrofurans has been achieved. The approach employs the asymmetric reduction of γ-phenylseleno ketones obtained by three different procedures that are peculiarly applied to the synthesis of such compounds. Finally, the intramolecular substitution of the phenylselenone residue by the oxygen atom of a hydroxy group gives the tetrahydrofuran ring.

One-pot asymmetric synthesis of 2-and 2,3-disubstituted tetrahydrofuran derivatives

A novel and convenient one-pot asymmetric synthesis of 2- and 2,3-disubstituted tetrahydrofurans has been achieved in 56-81% yields and 86-99% ee from aliphatic and aromatic aldehydes via an allyl/crotyl/ alkoxyallylboration-hydroboration-iodination-cyclization reaction sequence.