887-15-0

Usage

Uses

Used in Organic Synthesis:
2,2-diphenyltetrahydrofuran is used as a reagent in organic synthesis for the preparation of various types of compounds such as pharmaceuticals, agrochemicals, and flavors. Its unique structure and reactivity contribute to the synthesis of a wide range of chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-diphenyltetrahydrofuran is used as a key intermediate in the synthesis of various drug molecules. Its versatility allows for the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
2,2-diphenyltetrahydrofuran is utilized as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and stability make it suitable for the development of effective and environmentally friendly agrochemical products.
Used in Flavor Industry:
In the flavor industry, 2,2-diphenyltetrahydrofuran is used as a precursor for the synthesis of various flavor compounds. Its unique structure allows for the creation of novel and complex flavor profiles for use in food and beverage products.

InChI:InChI=1/C16H16O/c1-3-8-14(9-4-1)16(12-7-13-17-16)15-10-5-2-6-11-15/h1-6,8-11H,7,12-13H2

Upstream product

• 60-29-7 diethyl ether 
• 406-20-2 4-fluoro-butyric acid methyl ester 
• 1023-94-5 1,1-diphenylbutan-1,4-diol 
• 201230-82-2 carbon monoxide 
• 591-51-5 phenyllithium 
• 109-64-8 1,3-dibromo-propane 
• 75732-50-2 (2,2-dioxo-2λ⁶-[1,2]oxathiolan-3-yl)-diphenyl-methanol 
• 5785-66-0 cyclopropyl diphenyl carbinol 
• 100-59-4 phenylmagnesium chloride 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 108-86-1 bromobenzene 
• 4165-79-1 1,1-diphenyl-3-buten-1-ol 
• 56740-71-7 4,4-diphenyl-1-butanol 
• 884-73-1 2,2'-diphenyloxetane 

Downstream Products

• 76694-24-1 4,4-diphenyl-3-buten-1-ol 
• 107686-13-5 4,4-Diphenyl-hept-6-en-1-ol 
• 101167-47-9 3,4-dibromo-4,4-diphenyl-butan-1-ol 
• 1618101-67-9 2-phenyl-2-(o-tolyl)tetrahydrofuran 
• 1618101-68-0 2-(2-ethylphenyl)-2-phenyltetrahydrofuran 
• 1618101-69-1 2-(2-tributylstannylphenyl)-2-phenyltetrahydrofuran 
• 1618101-70-4 2-(2-(phenylthio)phenyl)-2-phenyltetrahydrofuran 
• 1618101-71-5 (2-(2-phenyltetrahydrofuran-2-yl)phenyl)diphenylphosphine 
• 1618101-74-8 2-(2-phenyltetrahydrofuran-2-yl)benzaldehyde 
• 1618101-75-9 [2-(2-phenyltetrahydrofuran-2-yl)phenyl]phenylmethanone 
• 1618101-76-0 2-(2-phenyltetrahydrofuran-2-yl)-N-(p-tolyl)benzamide 
• 1618101-77-1 ethyl 2-(2-(2-phenyltetrahydrofuran-2-yl)benzyl)acrylate 
• 1618101-79-3 1-[2-(2-phenyltetrahydrofuran-2-yl)phenyl]cyclohexanol 
• 1618101-80-6 2-(2-(2-phenyltetrahydrofuran-2-yl)phenyl)propan-2-ol 

Relevant academic research and scientific papers

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis

A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.

Grignard Reagents on a Tab: Direct Magnesium Insertion under Flow Conditions

An on-demand preparation of organomagnesium reagents is presented using a new flow protocol. The risks associated with the activation of magnesium are circumvented by a new on-column initiation procedure. Required amounts of solutions with a precise titration were obtained. Telescoped flow or batch reactions allow access to a diverse set of functional groups.

Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration

A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.

Regioselective desymmetrization of diaryltetrahydrofurans via directed ortho-lithiation: An unexpected help from green chemistry

An efficient functionalization of diaryltetrahydrofurans via a regioselective THF-directed ortho-lithiation is first described. This reaction can be successfully carried out in cyclopentyl methyl ether as a greener alternative to Et2O, with better results in terms of yield and selectivity and, surprisingly, also in protic eutectic mixtures competitively with protonolysis.

Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration

A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.

Stereospecific consecutive epoxide ring expansion with dimethylsulfoxonium methylide

Figure presented. Consecutive ring-expansion reactions of oxiranes with dimethylsulfxonium methylide were studied experimentally and modeled computationally at the density functional theory (DFT) and second-order Moller-Plesset (MP2) levels of theory utilizing a polarizable continuum model (PCM) to account for solvent effects. While the epoxide to oxetane ring expansion requires 13-17 kcal mol-1 activation and occurs at elevated temperatures, the barriers for the ring expansions to oxolanes are higher (ca. 25 kcal mol-1) and require heating to 125 °C. Further expansions of these oxolanes to the six-membered oxanes are hampered by high barriers (ca. 40 kcal mol-1). We observe the complete conservation of the enantiomeric purities for the nucleophilic ring expansions of enantiomeric 2-mono- and 2,2-disubstituted epoxides and oxetanes with dimethylsulfoxonium methylide. This is a convenient general approach for the high-yielding preparation of optically active four- and five-membered cyclic ethers from oxiranes.

Molybdenum- and rhenium-catalyzed isomerization of cyclopropanemethanols to tetrahydrofurans

Molybdenum- and rhenium-complexes work as affective catalysts for isomerization of a variety of cyclopropanemethanols into the corresponding tetrahydrofurans in good to high yields. The reaction may proceed via 1) [3,3]sigmatropic rear-rangement involving an oxo metal cyclopropanemethanolate accompanied by the C-C bond cleavage and 2) the metal-catalyzed intramolecular hydroalkoxylation of the initially produced homoallylic alcohols. Copyright

Reactions of Carbenes with Oxetane and with Oxetane/ Methanol Mixtures

Ethoxycarbonylcarbene, bis(methoxycarbonyl)carbene, phenylcarbene (17a), diphenylcarbene (17b), fluorenylidene (17c), 2-furylcarbene (31a), 2-furyl(phenyl)carbene (31b), 4-oxo-2,5-cyclohexadienylidene (40), and 4,4-dimethyl-2,5-cyclohexadienylidene (53) were generated by photolysis of the appropriate diazo compounds.With neat oxetane, most of these carbenes react by competitive C-H insertion (B -> A, Scheme 1) and ylide formation (B -> C). 31a and 40 do not insert into C-H bonds; 31b does not attack oxetane but rearranges exclusively with formation of 26.The ylides undergo Stevens rearrangement to give tetrahydrofurans (C -> D) and α',β-elimination, leading to allyl ethers (C -> E).With oxetane/ methanol mixtures, the intervention of oxonium ions (H) is indicated by the formation of 1,3-dialkoxypropanes (I).The oxonium ions arise either by protonation of the ylides (C -> H) or by protonation of the carbenes (B -> G), followed by electrophilic attack of the carbocations (G) at oxetane (G -> H).The former route is followed by the alkoxycarbonylcarbenes and by 40; the ylides derived from the remaining carbenes do not react with methanol, owing to their rapid Stevens rearrangements.Protonation of the carbenes 17b, 31, and 53 is clearly indicated by their product ratios and, for 31, by the formation of isomeric ethers (33, 36).The more electrophilic carbenes discriminate but slightly between oxetane and methanol while the more nucleophilic carbenes (17b, 31, 53) prefer the protic methanol strongly over the aprotic oxetane. Key Words: Carbenes/ Oxygen ylides/ Stevens rearrangement/ Oxonium ions/ Insertion, O-H/ Ylides

IMPROVED SYNTHESIS OF SUBSTITUTED OXETANES, TETRAHYDROFURANS, AND TETRAHYDROPYRANS FROM ω-CHLORINATED CARBOXYLIC ACID CHLORIDES

The reaction of β-chloropropanoyl chloride (1) with a Grignard reagent leads to the corresponding 1,3-chlorohydrin (2), which by treatment with potassium hydride yields a substituted oxetane (4).The use of γ-chlorobutyryl chloride (7) in the same reaction following by refluxing in tetrahydrofuran permits the direct isolation of the corresponding tetrahydrofuran (8) in an one-pot process.Finally, by adding an organomagnesium reagent to δ-chloropentanoyl chloride (11) the corresponding 1,5-chlorohydrin (12) is isolated; the treatment of the latter systems with sodium hydride at tetrahydrofuran reflux leads to the expected substituted substituted tetrahydropyran (13).

One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums

The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78 deg C, affords diarylalkylcarbinols in good yields.Alkyl chlorides do not react under similar experimental conditions.This feature makes the reaction particularly useful for the synthesisof alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols.The procedure can also be adapted to afford substituted cyclic ethers.If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful intermediates.With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields.