33417-17-3

Basic information

• Product Name: 3-hydroxy-3-acetonyl-2-oxindole
• Synonyms: 3-hydroxy-3-acetonyl-2-oxindole;3-Hydroxy-3-acetonyloxindole;1,3-Dihydro-3-hydroxy-3-(2-oxopropyl)-2H-indol-2-one;NSC 174507
• CAS NO: 33417-17-3
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.212
• Mol File: 33417-17-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 167-168℃ (Decomposition)
• Boiling Point: 450.2°Cat760mmHg
• Flash Point: 226.1°C
• Appearance: /
• Density: 1.301g/cm³
• Vapor Pressure: 6.84E-09mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 3-hydroxy-3-acetonyl-2-oxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-3-acetonyl-2-oxindole(33417-17-3)
• EPA Substance Registry System: 3-hydroxy-3-acetonyl-2-oxindole(33417-17-3)

Safety Data

• Hazardous Substances Data: 33417-17-3(Hazardous Substances Data)

Usage

General Description

3-hydroxy-3-acetonyl-2-oxindole is a chemical compound that belongs to the oxindole family. It is an intermediate in the biosynthesis of the group of antibiotics known as 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors, which are used to lower cholesterol levels. 3-hydroxy-3-acetonyl-2-oxindole is also a key component in the synthesis of certain natural products, including antitumor agents. Additionally, 3-hydroxy-3-acetonyl-2-oxindole has been studied for its potential anticancer and antimicrobial properties, making it an important compound in both pharmaceutical and chemical research.

InChI:InChI=1/C11H11NO3/c1-7(13)6-11(15)8-4-2-3-5-9(8)12-10(11)14/h2-5,15H,6H2,1H3,(H,12,14)

Upstream product

• 91-56-5 indole-2,3-dione 
• 109-89-7 diethylamine 
• 67-64-1 acetone 
• 700359-40-6 3-(2-oxopropyl)-3-tert-butyldimethylsilyl-oxyindolin-2-one 
• 220598-39-0 3-allyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 700359-39-3 3-allyl-3-tert-butyldimethylsilyloxyindolin-2-one 
• 541-50-4 2-acetoacetic acid 
• 109-77-3 malononitrile 
• 59-48-3 2-oxoindole 
• 1217-89-6 1-benzylisatin 

Downstream Products

• 76325-81-0 1,3-bis(3-hydroxy-3-oxindyl)-2-propanone 
• 634-38-8 2-methylquinoline-4-carboxylic acid 
• 91-56-5 indole-2,3-dione 
• 67-64-1 acetone 
• 3364-35-0 3-<2-Hydroxy-propyl>-indol 
• 500219-94-3 3-(2-hydroxypropyl)-3-hydroxy-2-oxindole 
• 79419-87-7 1-(4-Chloro-benzoyl)-3-imidazol-1-yl-3-(2-oxo-propyl)-1,3-dihydro-indol-2-one 
• 1383715-70-5 C₂₆H₂₁N₃O₃ 
• 1221577-88-3 (S)-3-hydroxy-3-((R)-2'-oxocyclohexyl)indolin-2-one 
• 1228658-39-6 (R)-3-hydroxy-3-((S)-2'-oxocyclohexyl)indolin-2-one 

Relevant articles and documents

Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone

Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.

Convolutamydine A and synthetic analogues have antinociceptive properties in mice

Convolutamydine A, an oxindole that originated from a marine bryozoan, has several biological effects. In this study, we aimed to investigate the antinociceptive effects of convolutamydine A and two new synthetic analogues. Convolutamydine A and the two analogues were given orally to assess their ability to induce antinociceptive effects. Formalin-induced licking response, acetic acid-induced contortions, and hot plate models were used to characterize the effects of convolutamydine A and its analogues. Convolutamydine A (4,6-bromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole), compound 1 (3-(2-oxopropyl)-3-hydroxy-2-oxindole), and compound 2 (5-bromo-3-(2-oxopropyl)- 3-hydroxy-2-oxindole) caused peripheral antinociceptive and anti-inflammatory effects in the acetic acid-induced contortions and the formalin-induced licking models. Supraspinal effects were also observed in the hot plate model and were similar to those obtained with morphine. The peripheral effects were not mediated by the cholinergic or opioid systems. The antinociceptive effects of convolutamydine A seem to be mediated by all three systems (cholinergic, opioid, and nitric oxide systems), and the mechanism of action of compounds 1 and 2 involved cholinergic and nitric oxide-mediated mechanisms. Convolutamydine A and its analogues (compounds 1 and 2) showed good antinociceptive ability after systemic administration in acute pain models. The antinociceptive action mediated by cholinergic, opioid, and nitric oxide systems could explain why convolutamydine A, compound 1, and compound 2 retained their antinociceptive effects. The doses used were similar to the doses of morphine and were much lower than that of acetylsalicylic acid, the classical analgesic and anti-inflammatory drug. In conclusion, convolutamydine A and the two analogues demonstrated antinociceptive effects comparable to morphine's effects.

Control of Chemical Reactions by Using Molecules that Buffer Non-aqueous Solutions

Control of chemical reactions is necessary to obtain designer chemical transformation products and for preventing decomposition and isomerization reactions of compounds of interest. For the control of chemical events in aqueous solutions, the use of aqueo

Cu(II)-thiophene-2,5-bis(amino-alcohol) mediated asymmetric Aldol reaction and Domino Knoevenagel Michael cyclization: A new highly efficient Lewis acid catalyst

The highly efficient Lewis acid-catalytic system Cu(II)-thiophene-2,5-bis(amino-alcohol) has been developed for enantioselective Aldol reaction of isatin derivatives with ketones. The new catalytic system also proved to be highly enantioselective for the one pot three-component Domino Knoevenagel Michael cyclization reaction of substituted isatin with malononitrile and ethylacetoacetate. The chiral ligand (2S,20S)-2,20-((thiophene-2,5-diylbis(methylene))bis(azanediyl))bis(3-phenylpropan-1-ol) (L1) in combination with Cu(OAc)2Η2O employed as a new Lewis acid catalyst, furnished 3-substituted-3- hydroxyindolin-2-ones derivatives (3a-s) in good to excellent yields (81-99%) with high enantioselectivities (up to 96% ee) and spiro[4H-pyran-3,3-oxindole] derivatives (6a-l) in excellent yields (89-99%) with high ee (up to 95%). These aldol products and spiro-oxindoles constitute a core structural motif in a large number of pharmaceutically active molecules and natural products.

Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.

A Continuous-Flow Route to Enantioenriched 3-Substituted-3-Hydroxyoxindoles: Organocatalytic Aldol Reactions of Isatin with Acetone

An efficient L-leucinol catalysed asymmetric synthesis of 3-substitued-3-hydroxyoxindoles was for the first time completed under continuous flow, providing a safer route for accelerating the reaction at higher temperatures without adversely affecting enan