874-23-7

Basic information

• Product Name: 2-ACETYLCYCLOHEXANONE
• Synonyms: alpha-Acetylcyclohexanone;2-Acetylcyclohexanone,98%;2-acetylcyclohexan-1-one;2-Acetylcyclohexanone,97%;2-ACETYLCYCLOHEXANONE FOR SYNTHESIS;2-Acetyl-1-cyclohexanone;2-acetyl-cyclohexanon;Acetylcyclohexanone
• CAS NO: 874-23-7
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• EINECS: 212-858-5
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 874-23-7.mol

Chemical Properties

• Melting Point: -11°C
• Boiling Point: 111-112 °C18 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 10.91±0.20(Predicted)
• Water Solubility: Not miscible in water.
• BRN: 1858621
• CAS DataBase Reference: 2-ACETYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYLCYCLOHEXANONE(874-23-7)
• EPA Substance Registry System: 2-ACETYLCYCLOHEXANONE(874-23-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 874-23-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetylcyclohexanone is used as a key intermediate in the synthesis of 1-(pyridyl)ethanol derivatives, which are used as reducing agents for keto-esters and ketones. These reducing agents are useful in the synthesis of various pharmaceutical compounds.
Used in Chemical Industry:
2-Acetylcyclohexanone is used in the synthesis of phenothiazine derivatives, which are a class of compounds with diverse applications. Some of these derivatives have been found to inhibit farnesyltransferase molecules, an enzyme involved in cell growth and division, and show anti-proliferative activity, making them potential candidates for the development of anti-cancer drugs.
Used in Research and Development:
2-Acetylcyclohexanone is used in the synthesis of anilinoethanolamines, which are compounds of interest in research and development. These compounds have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Purification Methods

Dissolve it in ligroin (b 30-60o), wash it with saturated aqueous NaHCO3, dry over Drierite and fractionate in a vacuum. [Perfetti & Levine J Am Chem Soc 75 626 1953, Manyik et al. J Am Chem Soc 75 5030 1953, Eistert & Reiss Chem Ber 87 108 1954.] It forms a Cu salt which crystallises in green leaflets from EtOH, m 162-163o [UV: McEntee & Pinder J Chem Soc 4419 1957].

InChI:InChI=1/C4H8O4/c5-3-4(6)8-2-1-7-3/h3-6H,1-2H2/t3-,4-/m0/s1

Upstream product

• 463-51-4 Ketene 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 108-24-7 acetic anhydride 
• 4056-73-9 2-acetyl-1,3-cyclohexanedione 
• 108-94-1 cyclohexanone 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 1424-22-2 1-cyclohexenyl acetate 
• 17216-03-4 2-α-Methoxyethyliden-cyclohexan-1-on 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 2261-02-1 acetylium tetrafluoroborate 
• 21173-96-6 1-(2-hydroxycyclohex-1-ene-1-yl)ethan-1-one 
• 64-19-7 acetic acid 

Downstream Products

• 58544-43-7 4-methyl-5,6,7,8-tetrahydro-quinazolin-2-ylamine 
• 142965-56-8 4-methyl-2-phenyl-5,6,7,8-tetrahydro-quinazoline 
• 14112-98-2 7-oxooctanoic acid 
• 64229-97-6 2-acetyl-2-chlorocyclohexan-1-one 
• 16275-33-5 2-(3-phenylpropanoyl)cyclohexanone 
• 90926-37-7 <2-Oxocyclohexyl>-1.3-butandion 
• 62269-46-9 1-(2-(trimethylsilyloxy)-1(Z)-cyclohexen-1-yl)-ethanone 
• 91900-64-0 2-Vinyl-2-acetyl-cyclohexanon-1 
• 1195-75-1 2-acetyl-2-methylcyclohexanone 
• 102569-88-0 2-((E)-3-Pyridin-4-yl-acryloyl)-6-[1-pyridin-4-yl-meth-(E)-ylidene]-cyclohexanone 
• 102569-80-2 2-((E)-3-Furan-2-yl-acryloyl)-6-[1-furan-2-yl-meth-(E)-ylidene]-cyclohexanone 
• 119-61-9 benzophenone 
• 99564-82-6 1-Trimethylsiloxy-2-<1-(trimethylsiloxy)vinyl>-1-cyclohexen 
• 107292-40-0 1-<2-<<2-(1H-Indol-3-yl)ethyl>amino>-1-cyclohexen-1-yl>ethanone 

Relevant articles and documents

Pyridone derivative and application thereof in preparation of medicine for preventing and/or treating tuberculosis caused by Mycobacterium tuberculosis

The invention provides a pyridone derivative and application thereof in preparation of a medicine for preventing and/or treating tuberculosis caused by mycobacterium tuberculosis, which belong to the field of pharmacy. The structure of the pyridone derivative is shown as a formula (I). Experimental results show that the pyridone derivative provided by the invention can specifically inhibit the activity of mycobacterium tuberculosis, has small toxic and side effects, can be used for preparing a medicine for resisting mycobacterium tuberculosis, can also be used for preparing a medicine for preventing and/or treating tuberculosis, and a new choice is provided for medicines for treating tuberculosis (especially drug-resistant tuberculosis).

SKLB1039 Compound as well as preparation method and application thereof

The invention belongs to the technical field of preparation of new compounds, and particularly relates SKLB1039 compound as well as a preparation method and application thereof. The 2 -methyl -3 -nitrobenzoic acid is taken as an initial raw material and is brominated. Esterification, reduction, reductive amination and hydrolysis synthesis 5 - bromo -2 - methyl -3 - (N - ethyl, N - (tetrahydropyran -4 - yl)) aminobenzoic acid. The cyclohexanone serving as a raw material is subjected to catalytic hydrogenation reduction of carbonyl α, acetyl cyclohexanone and cyanopyridone to synthesize 4 - aminomethyl -1 - methyl -5, 6, 7, 8 - tetrahydroisoquinoline -3 (2H) - ketone. Coupling the two to an amide is followed by catalytic coupling with an aryl sheet to give SKLB1039 a compound. SKLB1039 Large-scale preparation technology is provided, operation is easy, the post-treatment purification process is simple, the total route yield is improved, raw materials are easy to purchase, the price is low, and the production cost is greatly reduced.

Discovery of quinolone derivatives as antimycobacterial agents

Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.

ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT

A compound according to Formula (I) or a pharmaceutically acceptable salt and/or solvate thereof, wherein X1 and X2 are each independently 18F or 19F; R1 and R2 are each independently alkyl, amine, perfluoroalkyl, alkenyl, alkynyl, aryl, or aralkenyl; and R3 is H, halo, alkyl, alkyl ester, alkenyl, alkynyl, aryl, or aralkenyl; or wherein: R1 and R3 or R2 and R3 join to form a 6-membered cycloalkyl or heterocyclyl; or R1 and R3, R2 and R3, or R1, R2, and R3 join to form a substituted or unsubstituted polycyclic ring, wherein the polycyclic ring comprises fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings.

One-pot method for preparation of 2-acetyl cyclohexanone

The invention discloses a one-pot method for preparation of 2-acetyl cyclohexanone. The method comprises the steps of: (1) adding cyclohexanone into tetrahydrofuran, under the condition of icewater bath cooling, adding lithium diisopropylamide dropwise, and then carrying out stirring reaction at room temperature for 1h; (2) under the condition of icewater bath, adding a trichloromethane solution of acetyl chloride into the reaction system of step (1) dropwise, then removing icewater bath, and carrying out stirring reaction at room temperature for 1h; and (3) washing the reaction solution obtained in step (2) twice and performing liquid separation, conducting spin drying of trichloromethane, then carrying out pressure reduced distillation and collecting 118-136DEG C fractions, thus obtaining 2-acetyl cyclohexanone. According to the method, in the whole reaction process, the intermediate products have no need for additional purification treatment and can be directly subjected to next step reaction, and the finally obtained product is refined directly by pressure reduced distillation. The whole process has the advantages of high yield, short reaction time, and low energy consumption. The 2-acetyl cyclohexanone obtained by direct pressure reduced distillation refining has a concentration of more than 96.0wt%, and the yield is more than 94%.

Design, synthesis and biological evaluation of novel 1-methyl-3-oxo-2,3,5,6,7,8-hexahydroisoquinolins as potential EZH2 inhibitors

The histone lysine methyltransferase EZH2 has been implicated as a key component in cancer aggressiveness, metastasis and poor prognosis. This study discovered a new class of hexahydroisoquinolin derivatives as EZH2 inhibitors. A structure-activity relationship study showed that the steric hindrance was important to the activity for EZH2. A preliminary optimization study led to the discovery of several potent compounds with low nanomolar to sub-nanomolar potency for EZH2. Biological evaluation indicated that SKLB1049 was a highly potent with improved solubility compared to EPZ6438, SAM-competitive, and cell-active EZH2 inhibitor that decreased global H3K27me3 in SU-DHL-6 and Pfeiffer lymphoma cells in a concentration- and time-dependent manner. Further study indicated that SKLB1049 caused cell arrest in G0/G1 phase. These compounds would be useful as chemical tools to further explore the biology of EZH2 and provided us with a start point to develop new EZH2 inhibitors.

New bicyclic dioxanes, their preparation and their use as organoleptic compounds

The present invention relates to novel 1,3-dioxane derivatives of formula (I) wherein each of R1 and R2 is a hydrogen atom, R3 and R4 are independently a hydrogen atom, a linear or branched C1-C6 alkyl group, or a linear or branched C2-C6 alkenyl group, and R5 is a linear or branched C1-C6 alkyl group, a linear or branched C2-C6 alkenyl group or a (CH2)0-2 - aryl group, and R6 and R7 are independently a hydrogen atom, a linear or branched C1-C6 alkyl group, a linear or branched C2-C6 alkenyl group or a (CH2)0-2 - aryl group, or R6 and R7 together with the carbon atom to which they are attached form a C5-C6 cycloalkyl group or a C5-C6 cycloalkenyl group, substituted or not; their preparation and their use as organoleptic compounds.

NEW BICYCLIC DIOXANES, THEIR PREPARATION AND THEIR USE AS FRAGRANT COMPOUNDS

The invention is directed to the use of compounds of formula (I), as fragrant agents. In this formula: - R3 and R4 are independently a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkenyl group, R5 is a C1-C6 alkyl group, a C2-C6 alkenyl group or a (CH2)0-2-aryl group, R6 is a C1 -C6 alkyl group, a C2-C6 alkenyl group, a (CH2)0-2-aryl group or a C5- C6 cycloalkyl or cycloalkenyl group, and R7 is a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkenyl group; or R3, R4 and R5 are as above defined, and R6 and R7 together with the carbon atom to which they are attached form a C5-C6 cycloalkyl or cycloalkenyl group.

Titanium silicates as efficient catalyst for alkylation and acylation of silyl enol ethers under liquid-phase conditions

The activity of titanium- and tin-silicate samples such as TS-1, TS-2, Ti-β and Sn-MFI has been investigated for acylation and alkylation of silyl enol ethers under mild liquid-phase conditions. Silyl enol ethers successfully react with acetyl chloride and tert-butyl chloride under dry conditions in the presence of above catalysts to produce the corresponding acylated and alkylated products, respectively. In the case of acetylation reaction, two different nucleophiles with carbon-center (C-atom) and oxygen-center (O-atom) in silyloxy group of silyl enol ether reacts with acetyl chloride to give 1,3-diketone and ketene-ester, respectively. The selectivity for alkylation is always ca. 100% and no side products are formed. Among the various solvents investigated, anhydrous THF was found to be the suitable solvent for alkylation; whereas dichloromethane exhibited high selectivity for diketones for acylation. The formation of nucleophiles from silyl enol ethers appears to be the key step for successful acetylation and tert-butylation by nucleophilic reaction mechanism. Sn-MFI showed less activity than that observed over the titanosilicates. The observed catalytic activity is explained on the basis of "oxophilic Lewis acidity" of titanium silicate molecular sieves in the absence of H 2O under dry reaction conditions.

INDICYANINE DYES AND THE DERIVATIVES THEREOF FOR ANALYSING BIOLOGICAL MICROMOLECULES

The invention relates to two series of synthesised indolenine pentamethine dyes (37 compounds) comprising a reactive group in the third and fifth positions of the indolenine cycle, respectively. A method for producing, extracting and purifying the dyes and the precursors thereof, consisting in determining the absorption and fluorescence maxima, molecular extinction factors, fluorescence quantum yields, relative fluorescence effectiveness at excitation on a wavelength of 635 nm (detection of 670 nm) and 655 nm (detection of 690 nm), relative light stability and comparative sensitivity of detection of marked oligonucleotides on biochips of the claimed dyes, is disclosed. The use of the claimed dyes in the form of fluorescent marks for oligonucleotide and protein chips is also disclosed.