5323-87-5

Usage

Uses

Used in Organic Synthesis:
3-Ethoxy-2-cyclohexen-1-one is used as an intermediate for the preparation of 3-alkylor aryl-2-cyclohexen-1-ones, which are important in the field of organic chemistry. Its application is based on its ability to undergo addition reactions with organometallic reagents, followed by hydrolysis, to form the desired products.
Used in Alicyclic Synthesis:
In the specific area of alicyclic synthesis, 3-ethoxy-2-cyclohexen-1-one is used as a key component in the Stork-Danheiser kinetic alkylation procedure. This method involves kinetic enolate formation (LDA) and alkylation at the 6-position, which has found extensive use in creating alicyclic compounds with diverse structures and applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 3-ethoxy-2-cyclohexen-1-one, due to its role in organic synthesis, may also find applications in the pharmaceutical industry for the development of new drugs and medicinal compounds. Its ability to form various 3-alkylor aryl-2-cyclohexen-1-ones can be exploited in the synthesis of bioactive molecules with potential therapeutic properties.

InChI:InChI=1/C8H12O2/c1-2-10-8-5-3-4-7(9)6-8/h6H,2-5H2,1H3

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 75-03-6 ethyl iodide 
• 122-51-0 orthoformic acid triethyl ester 
• 64-17-5 ethanol 
• 112630-10-1 Dihydroresorcinol 
• 141-52-6 sodium ethanolate 
• 75700-18-4 3-<(Methanesulfonyl)oxy>-2-cyclohexenone 
• 1801-77-0 oxovanadium(V) ethoxydichloride 
• 102921-12-0 3-<<(4-methylphenyl)sulfonyl>hydrazino>cyclohex-2-en-1-one 
• 74-96-4 ethyl bromide 
• 50650-22-1 GENERIC INORGANIC CATION; 3-oxo-cyclohex-1-enolate 
• 30182-67-3 1,3-Cyclohexanedione 
• 141-78-6 ethyl acetate 
• 57918-73-7 3-acetoxy-cyclohex-2-enone 

Downstream Products

• 6301-49-1 3-butylcyclohexenone 
• 854726-99-1 2'-methyl-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one 
• 6301-52-6 3-biphenyl-3-yl-cyclohex-2-enone 
• 1193-18-6 3-methylcyclohexen-2-one 
• 6328-22-9 3-isopropyl-2-cyclohexen-1-one 
• 6328-24-1 3-propyl-2-cyclohexen-1-one 
• 10345-87-6 3-phenylcyclohex-2-enone 
• 930-68-7 cyclohexenone 
• 7122-91-0 [1,1'-bi(cyclohexan)]-1-en-3-one 
• 40996-91-6 3-vinyl-cyclohex-2-enone 
• 30530-40-6 (3-oxo-cyclohex-1-enyl)-acetic acid methyl ester 
• 108849-44-1 (3-ethoxycarbonylmethyl-cyclohex-2-enyliden)-acetic acid ethyl ester 
• 17159-98-7 3-(4-methoxyphenyl)-2-cyclohexen-1-one 
• 82942-79-8 3'-methyl-5,6-dihydro[1,1'-biphenyl]-3(4H)-one 

Relevant academic research and scientific papers

Primary Aminothiourea-Catalyzed Enantioselective Synthesis of Rauhut-Currier Adducts of 3-Arylcyclohexenone with a Tethered Enone on the Aryl Moiety at the Ortho -Position

An enantioselective synthesis of Rauhut-Currier (RC) adducts from 3-aryl cyclohexenone with a tethered enone moiety at the ortho-position on the aryl group is accomplished. This method provides a wide range of valuable synthetic building blocks having a unique [6-5-6] all-carbon-fused tricyclic skeleton. A primary amine-containing thiourea, a bifunctional organocatalyst, was found to be an efficient catalyst for this transformation. The primary amine counterpart of the catalyst possibly activates the aliphatic enone via dienamine formation (HOMO activation), whereas the thiourea counterpart activates the tethered enone (LUMO activation). Considering the difficulty in achieving an RC reaction of β,β-disubstituted (alkyl and aryl) enones, this method would be significantly rewarding.

Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction

Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels-Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.

Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine

We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (?)-mesembrine have been completed divergently.

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters

An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.

DIHYDROPYRIMIDINE DERIVATIVES AND USES THEREOF IN THE TREATMENT OF HBV INFECTION OR OF HBV-INDUCED DISEASES

Provided herein are dihydropyrimidine derivatives which are useful in the treatment of HBV infection or HBV-induced diseases, as well as pharmaceutical or medical applications thereof.

Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones

We report a total synthesis of the pyridine-containing limonoid alkaloid (-)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.

Synthesis of novel ent-kaurane-type diterpenoid derivatives effective for highly aggressive tumor cells

We have designed and synthesized 6 ent-Kaurane-type diterpenoid derivatives containing α,β-unsaturated ketone moieties. In vitro, activity was evaluated against three human tumor cell lines and a rat myogenic cell line (HepG2, NSCLC-H292, SNU-1040, L6) by MTT assay. All the tested compounds exhibited comparable or higher activity than DDP and eriocalyxin B. Compounds 16, 17 and 18 are promising anti-tumor leads due to their cytotoxic potencies and higher selectivity, with SI values of 161.06, 47.80 and 128.20, respectively.

Synthesis of chiral seven-membered β-substituted lactams: Via Rh-catalyzed asymmetric hydrogenation

Rh/bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of seven-membered β-substituted α,β-unsaturated lactams was successfully developed to prepare various chiral seven-membered β-substituted lactams with good to excellent results (up to >99% conversion, 99% yield, and >99% ee).

An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane

An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).