24539-92-2

Basic information

• Product Name: 5'-ETHYL-2'-HYDROXYACETOPHENONE
• Synonyms: 1-(5-ETHYL-2-HYDROXYPHENYL)ETHANONE;2-ACETYL-4-ETHYLPHENOL;2-HYDROXY-5-ETHYL ACETOPHENONE;2-HYDROXY-5-ETHYLPHENYL METHYL KETONE;5'-ETHYL-2'-HYDROXYACETOPHENONE;5-ETHYL-2-HYDROXYACETOPHENONE;Ethanone,1-(5-ethyl-2-hydroxyphenyl)-
• CAS NO: 24539-92-2
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 24539-92-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 110°C/5mm
• Flash Point: 114.1 °C
• Appearance: /
• Density: 1.078 g/cm³
• Vapor Pressure: 0.00346mmHg at 25°C
• Refractive Index: 1.539
• PKA: 10.50±0.18(Predicted)
• CAS DataBase Reference: 5'-ETHYL-2'-HYDROXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-ETHYL-2'-HYDROXYACETOPHENONE(24539-92-2)
• EPA Substance Registry System: 5'-ETHYL-2'-HYDROXYACETOPHENONE(24539-92-2)

Safety Data

• Hazardous Substances Data: 24539-92-2(Hazardous Substances Data)

Usage

Preparation

Preparation by Fries rearrangement of 4-ethylphenyl acetate with aluminium chloride without solvent at 115–120°.

InChI:InChI=1/C10H12O2/c1-3-8-4-5-10(12)9(6-8)7(2)11/h4-6,12H,3H2,1-2H3

Upstream product

• 63446-76-4 1-methyl-1,3-bis(trimethylsilyloxy)buta-1,3-diene 
• 30989-69-6 2-(diethoxymethyl)-1,1-diethoxybutane 
• 108-95-2 phenol 
• 99-93-4 4-Hydroxyacetophenone 
• 123-07-9 4-Ethylphenol 
• 75-36-5 acetyl chloride 
• 3245-23-6 p-ethylphenyl acetate 

Downstream Products

• 107368-92-3 (+/-)-cis-trikentrin A 
• 161988-81-4 4-ethyl-2-(1-methyl-but-3-enyl)-phenol 
• 161988-82-5 4-ethyl-2-(1-methyl-but-3-enyl)-6-nitro-phenol 
• 161988-88-1 1-ethyl-3-(1-methyl-but-3-enyl)-4-triethylsilyloxy-benzene 
• 161988-83-6 4-ethyl-2-(1-methyl-but-3-enyl)-6-nitro-phenyl-trifluoromethanesulphonate 
• 1388722-79-9 6-ethyl-2'-chloro-4'-nitroflavone 
• 1388722-87-9 C₁₇H₁₄ClNO₂ 
• 672904-14-2 6-ethylchroman-4-one 
• 161988-80-3 4-ethyl-2-(1-hydroxy-1-methyl-but-3-enyl)-phenol 
• 71002-71-6 5-ethyl-2-hydroxy-3-nitroacetophenone 
• 837416-59-8 3-(1-phenyl-3-thiophen-2-yl-1H-pyrazol-4-yl)-acrylic acid 2-acetyl-4-ethyl-phenyl ester 
• 29643-58-1 1-(5-Ethyl-2-pentyloxy-phenyl)-ethanone 
• 29643-60-5 1-(5-Ethyl-2-isobutoxy-phenyl)-ethanone 
• 29643-55-8 1-(2-Ethoxy-5-ethyl-phenyl)-ethanone 

Relevant articles and documents

ROR-GAMMA INHIBITORS

The present invention relates to compounds of formula I and pharmaceutical compositions comprising compounds of formula I. Compounds of Formula I are useful in treatment of inflammatory, metabolic or autoimmune diseases which are mediated by RORy.

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors

Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.

Regioselective synthesis of 5-alkylsalicylates, 5-alkyl-2-hydroxy- acetophenones, and 5-alkyl-2-hydroxy-benzophenones by [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes

(Chemical Equation Presented) A variety of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones was regioselectively prepared by TiCl4 mediated formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3- tetraethoxypropanes.