63828-70-6

Basic information

• Product Name: 2-(4-Methoxyphenyl)-2-cyclohexen-1-one
• Synonyms: 2-(4-Methoxyphenyl)-2-cyclohexen-1-one
• CAS NO: 63828-70-6
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.24906
• Mol File: 63828-70-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Methoxyphenyl)-2-cyclohexen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxyphenyl)-2-cyclohexen-1-one(63828-70-6)
• EPA Substance Registry System: 2-(4-Methoxyphenyl)-2-cyclohexen-1-one(63828-70-6)

Safety Data

• Hazardous Substances Data: 63828-70-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
2-(4-Methoxyphenyl)-2-cyclohexen-1-one is used as a fragrance ingredient for its pleasant floral odor, contributing to the creation of perfumes and other scented products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-(4-Methoxyphenyl)-2-cyclohexen-1-one is utilized as a key intermediate in the synthesis of various organic compounds and pharmaceuticals, playing a crucial role in the development of new medications.
Safety and Storage:
It is essential to handle 2-(4-Methoxyphenyl)-2-cyclohexen-1-one with care due to its potential to cause skin and eye irritation. Proper storage is also necessary to maintain its stability, requiring a cool, dry environment away from heat and direct sunlight.

Upstream product

• 56923-16-1 1-hydroxyimino-2-(4-methoxyphenyl)-2-cyclohexene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 77326-17-1 Trimethyl-(7-oxa-bicyclo[4.1.0]hept-2-en-2-yloxy)-silane 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 930-68-7 cyclohexenone 
• 50870-61-6 2-bromocyclohex-2-en-1-one 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 190256-71-4 (R)-2-(4-methoxyphenyl)cyclohexan-1-one 
• 43050-21-1 2-(4'-Methoxyphenyl)-3-hydroxy-cyclohexen 
• 1448846-71-6 2-(4-methoxylphenyl)-6-(ethoxycarbonylmethyl)cyclohex-2-enone 
• 1359636-13-7 C₂₀H₁₈O₂ 
• 1359636-29-5 C₂₀H₂₀O₂ 
• 84211-10-9 oxime of 2e-(4-methoxyphenyl)-3e-phenylcyclohexanone 
• 195001-50-4 2-(4'-methoxyphenyl)-1-vinylcyclohex-2-en-1-ol 
• 107388-37-4 (2S,3S)-2-(4-Methoxy-phenyl)-3-phenylsulfanyl-cyclohexanone 
• 107388-41-0 (2S,3S)-2-(4-Methoxy-phenyl)-3-(4-methoxy-phenylsulfanyl)-cyclohexanone 

Relevant articles and documents

Aqueous chemoenzymatic one-pot enantioselective synthesis of tertiary α-aryl cycloketonesviaPd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation

An aqueous chemoenzymatic cascade reaction combining Pd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation (AH) was developed for enantioselective synthesis of tertiary α-aryl cycloketones in good yields and excellent enantioselectivities. The stereopreference of the enzyme in AH of α-aryl cyclohexenones was studied. An enantiocomplementary enzyme was obtained by site-directed mutation.

Asymmetric Hydrogenation of Racemic 6-Aryl 1,4-Dioxaspiro[4.5]decan-7-ones to Functionalized Chiral ?a'Aryl Cyclohexanols via a Dynamic Kinetic Resolution

A ruthenium-catalyzed asymmetric hydrogenation method for the synthesis of functionalized β-aryl cyclohexanols is described. With chiral spiro ruthenium catalyst (Ra,S,S)-5c, a series of racemic α-aryl cyclohexanones bearing a β-monoethylene ketal group were hydrogenated to the corresponding functionalized β-aryl cyclohexanols in high yields with enantioselectivity of up to 99% ee via a dynamic kinetic resolution. This protocol can be conducted on a decagram scale and provide potential approaches for the synthesis of optically active and densely functionalized aryl cyclohexanols.

Dynamic Kinetic Resolution of I-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters

An efficient asymmetric hydrogenation of racemic I-substituted cyclic β-ketoesters via dynamic kinetic resolution to provide chiral cyclic β-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-5 (Ir-SpiroSAP), a series of racemic I-Aryl/alkyl substituted cyclic β-ketoesters were hydrogenated to the corresponding chiral cyclic β-hydroxy esters in high yields (84-97%) with good to excellent enantioselectivities (69->99% ee) and cis,cis-selectivities (up to >99:1).

Synthesis of 2-Arylphenol Derivatives through a One-Pot Suzuki-Miyaura Coupling/Dehydrogenative Aromatization Sequence with Pd/C Catalysis

One-pot synthesis of 2-arylphenols starting from 2-iodo-2-cyclohexen-1-one and arylboronic acids through sequential Suzuki-Miyaura coupling/dehydrogenative aromatization with Pd/C catalysis has been developed. A range of arylboronic acids serve as substrates, including those containing electron-donating or electron-withdrawing groups. Additionally, one-pot synthesis of di- or trisubstituted phenols bearing a phenyl group at the ortho position are also generated by using 2-iodo-2-cyclohexen-1-one derivatives as substrate. In the present method, commercially available and easily removable Pd/C was employed as a catalyst without any ligands. The operationally simple procedure and accessible conditions were used to provide modified phenols as the sole product in moderate to high yields.

Asymmetric hydrogenation of α,α′-disubstituted cycloketones through dynamic kinetic resolution: An efficient construction of chiral diols with three contiguous stereocenters

Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α′-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane. Copyright

α-Arylation and alkynylation of cyclic -iodoenones using palladium-catalyzed cross-coupling reactions with trifluoroborate salts

An expeditious synthesis of -aryl- and -alkynylcyclohexenones is described and illustrated by palladium-catalyzed cross-coupling reaction of cyclic -iodoenones with potassium aryltrifluoroborate salts. This procedure offers easy access to -arylated and al

Simple palladium(II) precatalyst for suzuki-miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners

trans-PdBr(N-Succ)(PPh3)2 (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also demonstrated.

The α-arylation of α-bromo- and α-chloroenones using palladium-catalysed cross-coupling

The palladium-catalysed cross-coupling reaction of various arylboronic acids with α-bromoenones and α-chloroenones offers an operationally simple approach to the synthesis of both cyclic and acyclic α-arylenones.

Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C

The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(0)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 °C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(0)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.