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10276-21-8

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10276-21-8 Usage

General Description

4,4,5A-TRIMETHYLPERHYDRO-1-BENZOXIREN-2-ONE, also known as epi-isophyllone, is a chemical compound with the molecular formula C11H18O2. It is a bicyclic compound that contains a perhydro-1-benzoxiren-2-one ring system. 4,4,5A-TRIMETHYLPERHYDRO-1-BENZOXIREN-2-ONE is used in organic synthesis and chemical research, and its derivatives have been studied for their potential pharmacological activities. It has a distinct molecular structure that makes it a valuable intermediate in the production of various organic compounds and pharmaceuticals.

Check Digit Verification of cas no

The CAS Registry Mumber 10276-21-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,2,7 and 6 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 10276-21:
(7*1)+(6*0)+(5*2)+(4*7)+(3*6)+(2*2)+(1*1)=68
68 % 10 = 8
So 10276-21-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O2/c1-8(2)4-6(10)7-9(3,5-8)11-7/h7H,4-5H2,1-3H3/t7-,9+/m0/s1

10276-21-8 Well-known Company Product Price

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  • Aldrich

  • (404675)  Isophoroneoxide  99%

  • 10276-21-8

  • 404675-5G

  • 2,197.26CNY

  • Detail

10276-21-8SDS

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 Isophorone Oxide

1.2 Other means of identification

Product number -
Other names 4,4,6-Trimethyl-7-oxabicyclo[4.1.0]heptan-2-one

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

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More Details:10276-21-8 SDS

10276-21-8Relevant articles and documents

Inverse phase transfer catalysis. III.- Optimization of the epoxidation reaction of α,β-unsaturated ketones by hydrogen peroxide

Boyer, Bernard,Hambardzoumian, Araik,Roque, Jean-Pierre,Beylerian, Norair

, p. 6147 - 6152 (1999)

The epoxidation of chalcone using hydrogen peroxide in the presence of a base in a two-phase medium system following the so-called Inverse Phase Transfer Catalysis (IPTC) process was investigated. Careful examination of various parameters including surfactant concentration, pH, H2O2 decomposition side-reactions and epoxide ring-opening, allowed us to determine optimal experimental conditions.

Novel cyclic ketones for catalytic oxidation reactions

Yang, Dan,Yip, Yiu-Chung,Tang, Man-Wai,Wong, Man-Kin,Cheung, Kung-Kai

, p. 9888 - 9894 (1998)

In our effort to search for C2 symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11- membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%).

Epoxydation of activated olefins by solid bases

Figueras,Palomeque,Lopez,Palomeque,Lopez

, p. 150 - 156 (2002)

The epoxidation of 2,1-cyclohexenone and β-isophorone by H2O2 and tert-butyl hydroperoxide (TBHP) were investigated on catalysts: hydrotalcites activated in different conditions, fluorinated hydrotalcites, KF/Al2O3/s

Sustainable Epoxidation of Electron-Poor Olefins with Hydrogen Peroxide in Ionic Liquids and Recovery of the Products with Supercritical CO2

Bortolini, Olga,Campestrini, Sandro,Conte, Valeria,Fantin, Giancarlo,Fogagnolo, Marco,Maietti, Silvia

, p. 4804 - 4809 (2003)

An efficient procedure is described for the epoxidation of electron-deficient olefins, in particular Vitamin K3 and analogues, with aqueous basic solutions of hydrogen peroxide in different ambient temperature ionic liquids (ILs) [bmim+][X-] {[bmim +] = 1-butyl-3-methylimidazolium; [X-] = [BF 4-], [CF3SO3-], [PF 6-], [N(CF3SO2)2 -]}. Various factors affecting epoxide yield (in the range 80-99%), reaction rate and reproducibility have been examined. The almost quantitative extraction of the epoxides from the reaction media has been obtained with supercritical CO2. The ionic liquid was then recovered and reused in subsequent cycles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Two catalytic systems of l-proline/Cu(II) catalyzed allylic oxidation of olefins with tert-butyl hydroperoxide

Yu, Peng,Zhou, Yin,Yang, Yingwei,Tang, Ruiren

, p. 65403 - 65411 (2016)

The nontoxic and water-soluble l-proline combined with two different forms of copper(ii): recoverable Cu-Al hydrotalcite-like compounds (Cu-Al HTLcs) and water-soluble CuCl2, as a heterogeneous catalytic system (l-proline/Cu-Al HTLcs) and two-phase catalytic system (l-proline/CuCl2) to catalyze allylic oxidation with tert-butyl hydroperoxide. The results showed that l-proline/Cu(ii) is highly active for oxidizing isophorone (IP) into ketoisophorone (KIP). Maximum catalytic effects were afforded respectively under the optimal reaction conditions, which obtained 77.9% IP conversion with 74.3% KIP selectivity catalyzed by l-proline/Cu-Al HTLcs and 73.5% conversion with 81.6% selectivity by l-proline/CuCl2. Recycling experiments of the two catalytic systems of l-proline/Cu(ii) showed they are stable and recyclable for at least six cycles with appreciable catalytic activity. And various hydrocarbons could be smoothly transformed into corresponding ketones with satisfactory conversion and selectivity by the two catalytic systems.

Microwave Promoted Epoxidation of α,β-Unsaturated Ketones in Aqueous Sodium Perborate

Sharifi, Ali,Bolourtchian, Mohammad,Mohsenzadeh, Farshid

, p. 668 - 669 (1998)

A series of α,β-unsaturated ketones has been treated with sodium perborate in water and 1,4-dioxane under microwave irradiation to produce α,β-epoxyketones in good yields.

Ultrasound-assisted epoxidation of olefins and α,β-unsaturated ketones over hydrotalcites using hydrogen peroxide

Pillai, Unnikrishnan R.,Sahle-Demessie, Endalkachew,Varma, Rajender S.

, p. 2017 - 2027 (2003)

An efficient ultrasound-assisted epoxidation of olefins and α,βunsaturated ketones over hydrotalcite catalysts in the presence of hydrogen peroxide and acetonitrile is described. This general and selective protocol is relatively fast and is applicable to a wide variety of substrates.

Epoxidation of α,β-unsaturated ketones with sodium perborate

Straub, Thomas S.

, p. 663 - 664 (1995)

α,β-Unsaturated ketones are rapidly converted to epoxyketones at room temperature in aqueous sodium perborate in the presence of a phase transfer catalyst. Organic solvents can be used to modify the rate of epoxidation.

Metal-free allylic oxidation with molecular oxygen catalyzed by g-C 3N4 and N-hydroxyphthalimide

Liu, Guiyin,Tang, Ruiren,Wang, Zhen

, p. 717 - 722 (2014)

Polymeric graphitic carbon nitride (g-C3N4) is a layered graphite-like nitrogen-rich material, bearing the potential ability to reductively adsorb molecular oxygen for catalytic allylic oxidation. Furthermore, N-hydroxyphthalimide (NHPI) has been recognized as an efficient catalyst for aerobic oxidation of various organic compounds under mild conditions in the presence of various co-catalysts. We present here a promising strategy for employing such nitride-rich g-C3N4 combined with NHPI to form an all-organic metal-free composite and have examined its activity for allylic oxidation with molecular oxygen as the primary terminal oxidant. In the case of allylic oxidation α-isophorone catalyzed by g-C3N4/NHPI gave priority to its corresponding carbonyl compound and epoxide. The effects of various reaction conditions on the catalytic reaction were optimized, affording 74.8 % conversion with 44.4 % selectivity of ketoisophorone at 130 C in 5 h. Repeated runs demonstrated that the catalyst was stable for at least three cycles without noticeable loss of its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Electrosynthesis of hydrogen peroxide in room temperature ionic liquids and in situ epoxidation of alkenes

Tang, Michael Chi-Yung,Wong, Kwok-Yin,Chan, Tak Hang

, p. 1345 - 1347 (2005)

Hydrogen peroxide can be electrosynthesized from oxygen in [bmim][BF 4]-water and used in situ for the epoxidation of alkenes. The Royal Society of Chemistry 2005.

Epoxidation of Olefins Using Methyl(trifluoromethyl)dioxirane Generated in Situ

Yang, Dan,Wong, Man-Kin,Yip, Yiu-Chung

, p. 3887 - 3889 (1995)

-

Microwave-expedited olefin epoxidation over hydrotalcites using hydrogen peroxide and acetonitrile

Pillai, Unnikrishnan R,Sahle-Demessie, Endalkachew,Varma, Rajender S

, p. 2909 - 2911 (2002)

An efficient microwave-assisted epoxidation of olefins is described over hydrotalcite catalysts in the presence of hydrogen peroxide and acetonitrile. This general and selective protocol is extremely fast and is applicable to a wide variety of substrates.

-

Reusch et al.

, p. 2803,2809 (1966)

-

Preparation of SnO2/graphene nanocomposite and its application to the catalytic epoxidation of alkenes with H2O2

Liu, Min,Wang, Xiaozhong,Chen, Yingqi,Dai, Liyan

, p. 61481 - 61485 (2015)

The in situ growth of SnO2 nanoparticles on graphene have been achieved via a hydrothermal method and the nanocomposites were used as an efficient catalyst for the epoxidation of alkenes with aqueous hydrogen peroxide in nitrile based systems for the first time. Furthermore, the SnO2/graphene nanocomposites could be readily recovered and reused for at least ten consecutive cycles without significant loss of activity and selectivity.

Improving the Monooxygenase Activity and the Regio- and Stereoselectivity of Terpenoid Hydroxylation Using Ester Directing Groups

Hall, Emma A.,Sarkar, Md. Raihan,Lee, Joel H. Z.,Munday, Samuel D.,Bell, Stephen G.

, p. 6306 - 6317 (2016/09/09)

The monooxygenase enzyme CYP101B1, from Novosphingobium aromaticivorans DSM12444, binds norisoprenoids more tightly than monoterpenoids and oxidized these substrates with high regioselectivity. Ionols bound less tightly to CYP101B1 than ionones, but the levels of product formation remained high and the selectivity of oxidation was similar to that observed for the parent norisoprenoid. The structurally related sesquiterpene lactone (+)-sclareolide (9) was stereoselectively hydroxylated by CYP101B1 to (S)-(+)-3-hydroxysclareolide (9a). The turnover of monoterpenoid derivatives showed low levels of product formation and selectivity despite promising binding data. CYP101B1 catalyzed the selective oxidation of (1R)-(-)-nopol (14) and cis-jasmone (15), generating >90% (1R)-(-)-5-hydroxynopol (14a) and 4-hydroxy-cis-jasmone (15a), respectively. To develop strategies for the efficient and selective oxidation of monoterpenoid-based substrates using CYP101B1, we investigated the binding and catalytic properties of terpenoid acetates. The ester functional group of these substrates mimicked the carbonyl moiety of norisoprenoids and anchored the monoterpenoid acetates in the active site of CYP101B1 with high affinity for the monoterpenoid acetates. The oxidation of these substrates by CYP101B1 occurred with product formation rates in excess of 1000 min-1 and total turnover numbers of greater than 5000 being observed in all but one instance. Critically, the oxidations were regioselective, with several being stereoselective. (-)-Myrtenyl acetate (20) was oxidized regioselectively (>95%) to yield cis-4-hydroxy-myrtenyl acetate (20a), which was further oxidized to 4-oxomyrtenyl acetate (20b) using a whole-cell system, providing a biocatalytic route to generate intermediates used in the production of cannabinoid derivatives. The ester carbonyl moiety could also be used as a directing group also to enhance the activity and control the selectivity of P450-catalyzed reactions; for example, the turnover of l-(-)-bornyl acetate (18) and isobornyl acetate (19) by CYP101B1 generated 9-hydroxybornyl acetate (18a) and 5-exo-hydroxyisobornyl acetate (19a), respectively, as the sole products.

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