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1008-73-7 Usage

General Description

Dihydro-4-phenylfuran-2(3H)-one is a chemical compound with the molecular formula C10H10O2. It is a cyclic enone and is commonly used in organic synthesis as a key intermediate in the production of pharmaceuticals and other complex organic compounds. This chemical is known for its distinctive aromatic smell and has been found to have potential applications in the fragrance and flavor industry. Additionally, dihydro-4-phenylfuran-2(3H)-one has shown promising biological activities, making it a subject of interest in medicinal chemistry research. Its versatile properties and structural features make it a valuable building block in the development of new chemical entities with diverse applications.

Check Digit Verification of cas no

The CAS Registry Mumber 1008-73-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,0 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1008-73:
(6*1)+(5*0)+(4*0)+(3*8)+(2*7)+(1*3)=47
47 % 10 = 7
So 1008-73-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O2/c11-10-6-9(7-12-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

1008-73-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-HYDROXY-3-PHENYLBUTANOIC ACID, .γ.-LACTONE

1.2 Other means of identification

Product number -
Other names 2(3H)-Furanone, dihydro-4-phenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1008-73-7 SDS

1008-73-7Relevant articles and documents

An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation

Imada, Yasushi,Iida, Hiroki,Murahashi, Shun-Ichi,Naota, Takeshi

, p. 1704 - 1706 (2005)

(Chemical Equation Presented) Highly chemoselective Baeyer-Villiger oxidations can be performed in the presence of other reactive functionalities such as alcohols, olefins, and sulfides, which would undergo electrophilic oxidation under conventional conditions (see scheme). [DMRFlEt] +[ClO4]- (depicted blue) is a new class of flavin compound that catalyzes aerobic Baeyer-Villiger oxidations in the presence of Zn dust as the electron source.

Acetic Acid as a Highly Reactive and Easily Separable Catalyst for the Oxidative Cleavage of Tetrahydrofuran-2-methanols to γ-Lactones

Yakura, Takayuki,Fujiwara, Tomoya,Nishi, Hideyuki,Nishimura, Yushi,Nambu, Hisanori

, p. 2316 - 2320 (2018)

[4-Iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid was developed as a highly reactive and easily separable catalyst for the oxidative cleavage of tetrahydrofuran-2-methanols to γ-lactones in the presence of Oxone (2KHSO 5 ·KHSO 4 ·K 2 SO 4) as the co-oxidant. The reactivity of this new catalyst was considerably greater than that of our previously reported catalyst, 2-iodo-N-isopropylbenzamide. The new catalyst and product were easily separated by only liquid-liquid separation without chromatography. In addition, using a mixture of nitromethane and N, N-dimethylformamide as the solvent and heating enabled a low catalyst loading, a short reaction time, and high product yield. Oxidative cleavage using the new catalyst can be used as a practical and efficient method for synthesizing γ-lactones.

Investigation of a New Type I Baeyer–Villiger Monooxygenase from Amycolatopsis thermoflava Revealed High Thermodynamic but Limited Kinetic Stability

Mansouri, Hamid R.,Mihovilovic, Marko D.,Rudroff, Florian

, p. 971 - 977 (2020)

Baeyer–Villiger monooxygenases (BVMOs) are remarkable biocatalysts, but, due to their low stability, their application in industry is hampered. Thus, there is a high demand to expand on the diversity and increase the stability of this class of enzyme. Sta

Silyl peroxides as effective oxidants in the Baeyer-Villiger reaction with chloroaluminate(III) ionic liquids as catalysts

Baj, Stefan,S?upska, Roksana,Chrobok, Anna,Drozdz, Agnieszka

, p. 120 - 126 (2013)

A new application of silyl peroxides as oxidants in the Baeyer-Villiger oxidation of cyclic ketones in chloroaluminate(III) ionic liquids is described. Among the silyl peroxides, the reactivity of two groups of peroxides was studied: bis(silyl) and t-butyl silyl peroxides possessing different structured substituents attached to the Si atom. It was shown that the acidic 1-hexyl-3-methylimidazolium chloroaluminate(III) ionic liquid (molar ratio of AlCl3 in ionic liquid: 0.67) present in the oxidation of cyclic ketones with bis(silyl) peroxides acts as the catalyst. In this variant of the reaction, the reactivities of bis(silyl) peroxides decrease in the following order: bis(trimethylsilyl) peroxide > bis(vinyldimethylsilyl) peroxide > bis(phenyldimethylsilyl) peroxide > bis(diphenylmethylsilyl) peroxide. A variety of cyclic ketones such as cyclobutanone, 3-substituted cyclobutanones, cyclopentanone, cyclohexanone, 2-methylcyclohexanone, 4-methylcyclohexanone, 2-adamantanone and norcamphor were oxidised to their corresponding lactones with high yields (49-100%). When t-butyl silyl peroxides and neutral chloroaluminate(III) ionic liquids (molar ratio of AlCl3 in ionic liquid: 0.5) were utilised in the Baeyer-Villiger oxidation, the studied ionic liquid acted as the reagent. Here, phenyldimethyl(t-butylperoxy)silane was the most efficient oxidant in the oxidation of cyclobutanone to γ- butyrolactone (70% yield). Other peroxides, including trimethyl(t-butylperoxy) silane, vinyldimethyl(t-butylperoxy)silane and diphenylmethyl-(t-butylperoxy) silane, were less reactive oxidants. Two variants of the Baeyer-Villiger reaction mechanism are postulated.

Asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones using a chiral cationic palladium(II) 2-(phosphinophenyl)pyridine complex as catalyst

Ito, Katsuji,Ishii, Ayako,Kuroda, Tomomi,Katsuki, Tsutomu

, p. 643 - 646 (2003)

Chiral cationic palladium(II) 2-(phosphinophenyl)pyridine (1a) complex was found to be an effective catalyst for asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones. For example, good and excellent enantioselectivities (80% and >99% ees) were

Highly enantioselective Baeyer-Villiger oxidation using Zr(salen) complex as catalyst

Watanabe, Akira,Uchida, Tatsuya,Ito, Katsuji,Katsuki, Tsutomu

, p. 4481 - 4485 (2002)

(R,R)-Zr(salen) complex was found to serve as an efficient catalyst for asymmetric Baeyer-Villiger oxidation of pro-chiral and racemic ketones using urea·hydrogen peroxide as the terminal oxidant: for example, high enantioselectivity of 87% ee was achieve

Mechanistic investigation of chiral phosphoric acid catalyzed asymmetric baeyer-villiger reaction of 3-substituted cyclobutanones with H 2O2 as the oxidant

Xu, Senmiao,Wang, Zheng,Li, Yuxue,Zhang, Xumu,Wang, Haiming,Ding, Kuiling

, p. 3021 - 3035 (2010)

The mechanism of the chiral phosphoric acid catalyzed Baeyer-Villiger (B-V) reaction of cyclobutanones with hydrogen peroxide was investigated by using a combination of experimental and theoretical methods. Of the two pathways that have been proposed for the present reaction, the pathway involving a peroxyphosphate intermediate is not viable. The reaction progress kinetic analysis indicates that the reaction is partially inhibited by the y-lactone product. Initial rate measurements suggest that the reaction follows Michaelis-Menten-type kinetics consistent with a bifunctional mechanism in which the catalyst is actively involved in both carbonyl addition and the subsequent rearrangement steps through hydrogen-bonding interactions with the reactants or the intermediate. High-level quantum chemical calculations strongly support a two-step concerted mechanism in which the phosphoric acid activates the reactants or the intermediate in a synergistic manner through partial proton transfer. The catalyst simultaneously acts as a general acid, by increasing the electrophilicity of the carbonyl carbon, increases the nucleophilicity of hydrogen peroxide as a Lewis base in the addition step, and facilitates the dissociation of the OH group from the Criegee intermediate in the rearrangement step. The overall reaction is highly exothermic, and the rearrangement of the Criegee intermediate is the rate-determining step. The observed reactivity of this catalytic B-V reaction also results, in part, from the ring strain in cyclobutanones. The sense of chiral induction is rationalized by the analysis of the relative energies of the competing diastereomeric transition states, in which the steric repulsion between the 3-substituent of the cyclobutanone and the 3- and 3'-substituents of the catalyst, as well as the entropy and solvent effects, are found to be critically important.

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Mukaiyama,T. et al.

, p. 1207 - 1210 (1979)

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Construction of a new asymmetric reaction site: Asymmetric 1,4-addition of thiol using pentagonal bipyramidal Hf(salen) complex as catalyst

Matsumoto, Kazuhiro,Watanabe, Akira,Uchida, Tatsuya,Ogi, Kayoko,Katsuki, Tsutomu

, p. 2385 - 2388 (2004)

Pentagonal bipyramidal Hf(salen) complex 1 was found to serve as a catalyst for 1,4-addition reaction of thiol to N-(2-alkenoyl)-2-oxazolidinones.

Lactone Synthesis by α,ω-Diols with Hydrogen Peroxide Catalyzed by Heteropoly Acids Combined with Cetylpyridinium Chloride

Ishii, Yasutaka,Yoshida, Tsutomu,Yamawaki, Kazumasa,Ogawa, Masaya

, p. 5549 - 5552 (1988)

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Rational Construction of an Artificial Binuclear Copper Monooxygenase in a Metal-Organic Framework

Feng, Xuanyu,Song, Yang,Chen, Justin S.,Xu, Ziwan,Dunn, Soren J.,Lin, Wenbin

, p. 1107 - 1118 (2021)

Artificial enzymatic systems are extensively studied to mimic the structures and functions of their natural counterparts. However, there remains a significant gap between structural modeling and catalytic activity in these artificial systems. Herein we report a novel strategy for the construction of an artificial binuclear copper monooxygenase starting from a Ti metal-organic framework (MOF). The deprotonation of the hydroxide groups on the secondary building units (SBUs) of MIL-125(Ti) (MIL = Matériaux de l'Institut Lavoisier) allows for the metalation of the SBUs with closely spaced CuI pairs, which are oxidized by molecular O2 to afford the CuII2(μ2-OH)2 cofactor in the MOF-based artificial binuclear monooxygenase Ti8-Cu2. An artificial mononuclear Cu monooxygenase Ti8-Cu1 was also prepared for comparison. The MOF-based monooxygenases were characterized by a combination of thermogravimetric analysis, inductively coupled plasma-mass spectrometry, X-ray absorption spectroscopy, Fourier-transform infrared spectroscopy, and UV-vis spectroscopy. In the presence of coreductants, Ti8-Cu2 exhibited outstanding catalytic activity toward a wide range of monooxygenation processes, including epoxidation, hydroxylation, Baeyer-Villiger oxidation, and sulfoxidation, with turnover numbers of up to 3450. Ti8-Cu2 showed a turnover frequency at least 17 times higher than that of Ti8-Cu1. Density functional theory calculations revealed O2 activation as the rate-limiting step in the monooxygenation processes. Computational studies further showed that the Cu2 sites in Ti8-Cu2 cooperatively stabilized the Cu-O2 adduct for O-O bond cleavage with 6.6 kcal/mol smaller free energy increase than that of the mononuclear Cu sites in Ti8-Cu1, accounting for the significantly higher catalytic activity of Ti8-Cu2 over Ti8-Cu1.

The rationale for stereoinduction in conjugate addition to alkylidenemalonates bearing a menthol-derived chiral auxiliary

Yamada, Ken-ichi,Fujiwara, Shinichi,Inokuma, Tsubasa,Sugano, Masayuki,Yamaoka, Yousuke,Takasu, Kiyosei

, (2021)

Density-functional theory (DFT) calculations provided a new model to rationalize the stereoselectivity in the asymmetric addition to alkylidenemalonate bearing 8-phenylmenthyl groups as a chiral auxiliary. The diastereoselectivity in the addition reactions of a tetramethyldioxolanyl radical with various alkyl 8-phenylmenthyl benzylidenemalonates strongly supports the proposed model.

Pyrazinium salts as efficient organocatalysts of mild oxidations with hydrogen peroxide

Menova, Petra,Kafka, Frantisek,Dvorakova, Hana,Gunnoo, Smita,Sanda, Miloslav,Cibulka, Radek

, p. 865 - 870 (2011)

A series of 3-substituted pyrazinium tetrafluoroborates was prepared as simple analogues of flavinium salts which are efficient organocatalysts for oxidations with hydrogen peroxide. It was shown that pyrazinium derivatives with an electron-withdrawing su

Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer-Villiger oxidation and epoxidation with chiral ligands

Bolm, Carsten,Beckmann, Oliver,Kuehn, Toralf,Palazzi, Chiara,Adam, Waldemar,Rao, Paraselli Bheema,Saha-Moeller, Chantu R.

, p. 2441 - 2446 (2001)

Chiral hydroperoxides have a significant influence on the enantioselectivity of the metal-catalyzed asymmetric Baeyer-Villiger oxidation of cyclic ketones and the epoxidation of allylic alcohols, when chiral ligands are employed. If both the ligand and th

(R)-3,5-diCF3-SYNPHOS and (R)- p -CF3-SYNPHOS, electron-poor diphosphines for efficient room temperature Rh-catalyzed asymmetric conjugate addition of arylboronic acids

Berhal, Farouk,Esseiva, Olivier,Martin, Charles-Henri,Tone, Hitoshi,Genet, Jean-Pierre,Ayad, Tahar,Ratovelomanana-Vidal, Virginie

, p. 2806 - 2809 (2011)

Two new atropisomeric electron-poor chiral diphosphine ligand analogues of SYNPHOS were prepared, and their electronic properties are described. These two ligands afforded high performance for the Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds at room temperature.

Asymmetric 1,4-hydrosilylations of α,β-unsaturated esters

Lipshutz, Bruce H.,Servesko, Jeff M.,Taft, Benjamin R.

, p. 8352 - 8353 (2004)

Complexing catalytic amounts of CuH with a nonracemic JOSIPHOS or SEGPHOS ligand, together with stoichiometric PMHS, leads to exceedingly efficient and highly enantioselective 1,4-reductions of β,β-disubstituted enoates and lactones. An unprecedented subs

Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5- cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride

Kina, Asato,Ueyama, Kazuhito,Hayashi, Tamio

, p. 5889 - 5892 (2005)

(Chemical Equation Presented) A rhodium complex coordinated with 1,5-diphenyl-1,5-cyclooctadiene (Ph-cod), [RhCl((R)-Ph-cod)]2, was obtained enantiomerically pure through optical resolution of diastereomeric isomers [Rh(Ph-cod)((R)-1,1′-binapht

Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes

Kurihara, Kazunori,Sugishita, Noriyuki,Oshita, Kengo,Piao, Dongguo,Yamamoto, Yasunori,Miyaura, Norio

, p. 428 - 435 (2007)

A chiral bidentate phosphoramidite (5a) was synthesized from Shibasaki's linked-(R)-BINOL and P(NMe2)3 as a new ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds. The effects of 5a and Feringa's monodentate phosphoramidite (4, R1, R2 = Et) on the yields and enantioselectivities were fully investigated. The reaction was significantly accelerated in the presence of a base such as KOH and Et3N, allowing the reaction to be completed at the lower temperatures than 50 °C. The addition to cyclic enones such as 2-cyclopentenone, 2-cyclohexenone and 2-cycloheptenone at 50 °C in the presence of an [Rh(coe)2Cl]2-4 (R1, R2 = Et) complex resulted in enantioselectivities up to 98%, though it was less effective for acyclic enones (0-70% ee). On the other hand, a complex between [Rh(nbd)2]BF4 and 5a completed the addition to cyclic enones within 2 h at room temperature in the presence of Et3N with 86-99% yields and 96-99.8% ee. This catalyst was also effective for acyclic enones, resulting in 62-98% yields and 66-94% ee. The 1,4-additions of arylboronic acids to unsaturated lactones and acyclic esters with rhodium(I)-phosphoramidites complexes were also investigated.

The mutagenesis of a single site for enhancing or reversing the enantio- or regiopreference of cyclohexanone monooxygenases

Hu, Yujing,Xu, Weihua,Hui, Chenggong,Xu, Jian,Huang, Meilan,Lin, Xianfu,Wu, Qi

, p. 9356 - 9359 (2020)

The mutagenesis of a "second sphere"switch residue of CHMOAcineto could control its enantio- and regiopreference. Replacing phenylalanine (F) at position 277 of CHMOAcineto into larger tryptophan (W) enabled a significant enhancement of enantio- or regioselectivity toward structurally diverse substrates, moreover, a complete reversal of enantio- or regiopreference was realized by mutating F277 into a range of smaller amino acids (A/C/D/E/G/H/I/K/L/M/N/P/Q/R/S/T/V).

Phosphothreonine (pThr)-Based Multifunctional Peptide Catalysis for Asymmetric Baeyer-Villiger Oxidations of Cyclobutanones

Featherston, Aaron L.,Shugrue, Christopher R.,Mercado, Brandon Q.,Miller, Scott J.

, p. 242 - 252 (2019)

Biologically inspired phosphothreonine (pThr)-embedded peptides that function as chiral Br?nsted acid catalysts for enantioselective Baeyer-Villiger oxidations (BV) of cyclobutanones with aqueous H2O2 are reported herein. Complementa

Chiral Bronsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2

Xu, Senmiao,Wang, Zheng,Zhang, Xue,Zhang, Xumu,Ding, Kuiling

, p. 2840 - 2843 (2008)

(Chemical Equation Presented) A catalytic amount of a chiral Bronsted acid with aqueous H2O2 as the oxidant is sufficient for the enantioselective Baeyer-Villiger oxidation of 3-substituted cyclobutanones to give the corresponding γ-

Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric baeyer-villiger reaction

Bolm, Carsten,Frison, Jean-Cédric,Zhang, Yu,Wulff, William D.

, p. 1619 - 1621 (2004)

Vaulted biaryls (VANOL and VAPOL) have been applied in the aluminum-catalyzed asymmetric Baeyer-Villiger reaction of prochiral 3-substituted cyclobutanones. Optically active γ-butyrolactones are obtained in high yields with enantioselectivities of up to 84% ee.

Regioselectivity in Nickel(II)-Mediated Oxidations of Diols

Doyle, Michael P.,Dow, Robert L.,Bagheri, Vahid,Patrie, William, J.

, p. 476 - 480 (1983)

Oxidations of 2- and 4-substituted 1,4-butanediols to their corresponding γ-butyrolactones by the combination of molecular bromine and nickel(II) alkanoate occur with a high degree of regioselectivity.The influence of the alkanoate ligand, of substituents at the 2-position of 1,4-butanediols, and of solvent on oxidation regiocontrol is examined, and comparison of regioselectivity in diol oxidations is made with representative conventional oxidative methods.Regiocontrol in nickel(II)-mediated reactions is proposed to be derived from steric constraints for oxidativehydrogen transfer to the alkanoate ligand of nickel(II) in the diol-associated complex.Alternate use of cobalt(II) alkanoates provides regiocontrol in diol oxidations that is comparable or superior to that obtained with nickel(II) alkanoates in bromine oxidations.

Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis

Jang, Won Jun,Yun, Jaesook

, p. 18131 - 18135 (2019)

We report the catalytic enantioselective conjugate addition of a borylalkyl copper nucleophile generated in situ from a 1,1-diborylmethane derivative to α,β-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)–copper catalyst, this method facilitated the enantioselective incorporation of a CH2Bpin moiety at the β-position of the diesters to yield β-chiral alkyl boronates in up to 86 % yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C?B bond.

Enantioselective Baeyer-Villiger oxidations catalyzed by chiral magnesium complexes

Bolm,Beckmann,Cosp,Palazzi

, p. 1461 - 1463 (2001)

Catalytic enantioselective Baeyer-Villiger oxidations of 3-substituted cyclobutanones with cumene hydroperoxide as oxidant have successfully been performed in the presence of chiral magnesium catalysts. The combination of enantiopure BINOL and a variety o

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

Chan, Wei Chuen,Vinod, Jincy K.,Koide, Kazunori

, p. 3674 - 3682 (2021/02/16)

We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by experimental and density functional theory studies.

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