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33046-41-2

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33046-41-2 Usage

Synthesis Reference(s)

Tetrahedron, 51, p. 7937, 1995 DOI: 10.1016/0040-4020(95)00431-7

Check Digit Verification of cas no

The CAS Registry Mumber 33046-41-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,0,4 and 6 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 33046-41:
(7*3)+(6*3)+(5*0)+(4*4)+(3*6)+(2*4)+(1*1)=82
82 % 10 = 2
So 33046-41-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H14O/c1-11(13)7-5-6-10-12-8-3-2-4-9-12/h2-5,7-9H,6,10H2,1H3/b7-5+

33046-41-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Phenylhex-3-en-2-one

1.2 Other means of identification

Product number -
Other names -

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 -
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More Details:33046-41-2 SDS

33046-41-2Relevant academic research and scientific papers

Synthesis, in vitro reactivity, and identification of 6-phenyl-3-hexen-2- one in human urine after kava-kava (Piper methysticum) ingestion

Zou, Lihong,Harkey, Martha R.,Henderson, Gary L.

, p. 142 - 146 (2005)

This study describes the synthesis of 6-phenyl-3-hexen-2-one, a proposed metabolite of kava-kava (kava, 'Awa, Yaqona, Piper methysticum Forst.), its reactivity with glutathione in vitro, and its isolation and identification, as its mercapturic acid adduct using LC/MS/MS, in the urine of two human subjects following their ingestion of kava. A possible metabolic pathway for the formation of this metabolite and its possible role in hepatotoxicity are also discussed.

Synthesis of γ-Hydroperoxy-α,β-unsaturated Carbonyl Compounds from α,β,γ,δ-Unsaturated Carbonyl Compounds by Cobalt(II) Porphyrin-catalysed Hydroperoxygenation

Matsushita, Yoh-ichi,Sugamoto, Kazuhiro,Nakama, Tuyoshi,Matsui, Takanao

, p. 567 - 568 (1995)

γ-Hydroperoxy-α,β-unsaturated carbonyl compounds are prepared in good yields by the regioselective hydroperoxygenation of α,β,γ,δ-unsaturated carbonyl compounds with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst.

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

Pasha, Maira,Tanaka, Fujie

supporting information, p. 9242 - 9250 (2021/11/16)

Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is

Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes

Chen, Zi-Yan,Deng, Xue-Zu,Song, Yang,Xue, Fei,Yamane, Motoki,Yue, Yan-Ni

, p. 12693 - 12704 (2021/09/28)

We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.

Dehydrative Re2O7-Catalyzed Approach to Dihydropyran Synthesis

Lawrence, Jean-Marc I. A.,Floreancig, Paul E.

supporting information, p. 9513 - 9517 (2020/12/21)

Monoallylic 1,3- and 1,5-diols undergo Re2O7-mediated ionization to form allylic cations that engage in cyclization reactions to form dihydropyran products. The reactions give the 2,6-trans-stereoisomer as the major products as a result of minimizing steric interactions in a boat-like transition state. The results of these studies are consistent with cationic intermediates, with an intriguing observation of stereochemical retention in one example.

A Heck reaction/photochemical alkene isomerization sequence to prepare functionalized quinolines

Donohoe, Timothy J.,Hoff, Oskar,Hoffman, Jack B.,Kelly, Alex,Walker, Johannes C. L.,Werrel, Simon

, (2020/08/06)

A route to prepare functionalized quinolines based on a Heck reaction/UV-induced alkene isomerization sequence is described. The method allows for the preparation of quinolines under mild and neutral conditions and has broad functional group tolerance. Acid-sensitive functional groups that would not be tolerated under previous approaches can be included and a one-pot quinoline forming procedure is also reported.

Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis

Romano, Ciro,Fiorito, Daniele,Mazet, Clément

supporting information, p. 16983 - 16990 (2019/10/28)

The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.

Tandem hydroformylation/aldol condensation reactions: Synthesis of unsaturated ketones from olefins

Kollár, László,Pongrácz, Péter

, p. 184 - 188 (2018/05/07)

Platinum-catalysed tandem hydroformylation/aldol condensation reaction of vinyl aromatics and ketones toward the corresponding α,β-unsaturated ketones were performed under syngas atmosphere in the presence of acid co-catalysts. The in situ generated catal

Csp-Csp3 Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes

Shen, Yangyong,Huang, Bo,Zheng, Jing,Lin, Chen,Liu, Yu,Cui, Sunliang

supporting information, p. 1744 - 1747 (2017/04/11)

An iron(III)-promoted hydroalkynylation of unactivated alkenes toward Csp-Csp3 bond formation has been developed. Various alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified alkynes in this chemoselective protocol. Additionally, the scalability was unraveled and the further divergent transformations of products were conducted to demonstrate the synthetic utility.

Enantioselective NiH/Pmrox-Catalyzed 1,2-Reduction of α,β-Unsaturated Ketones

Chen, Fenglin,Zhang, Yao,Yu, Lei,Zhu, Shaolin

supporting information, p. 2022 - 2025 (2017/02/15)

The enantioselective 1,2-reduction of α,β-unsaturated ketones was achieved using a NiH catalyst in the presence of pinacolborane. This mild process represents a general method to access a wide variety of structurally diverse α-chiral allylic alcohols in excellent yields and enantioselectivity, as well as very high levels of ambidoselectivity for 1,2- over 1,4-reduction. Furthermore, for reactions on a 10 mmol scale, catalyst loadings as low as 0.5 mol % could be employed to deliver product without any detrimental effect on the yield, enantio-, or ambidoselectivity.

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