3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one

Base Information

• Chemical Name: 3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one
• CAS No.: 33417-17-3
• Molecular Formula: C11H11 N O3
• Molecular Weight: 205.213
• Hs Code.: 2933790090
• NSC Number: 659193,174507
• DSSTox Substance ID: DTXSID201036242
• Nikkaji Number: J2.037.588D
• ChEMBL ID: CHEMBL1708591
• Mol file: 33417-17-3.mol

Synonyms:3-hydroxy-3-acetonyl-2-oxindole;3-OHAI

Chemical Property of 3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one

Chemical Property:

• Vapor Pressure: 6.84E-09mmHg at 25°C
• Melting Point: 167-168℃ (Decomposition)
• Boiling Point: 450.2°Cat760mmHg
• Flash Point: 226.1°C
• PSA: 66.40000
• Density: 1.301g/cm³
• LogP: 0.94340
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-3-(2-oxo-propyl)-1,3-dihydro-indol-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC1(C2=CC=CC=C2NC1=O)O

Technology Process of 3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one

There total 14 articles about 3-Hydroxy-3-(2-oxopropyl)-1,3-dihydro-2H-indol-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + acetone (67-64-1) → 3-hydroxy-3-(2-oxopropyl)indolin-2-one (33417-17-3)

Guidance literature:

With 1,3,5-triazine-piperazine immobilised mesoporous silica; In neat (no solvent); at 20 ℃; for 6h; Reagent/catalyst;

DOI:10.1039/c5ra00406c

Reference yield: 92.0%

1-benzylisatin (1217-89-6) + acetone (67-64-1) → 3-hydroxy-3-(2-oxopropyl)indolin-2-one (33417-17-3)

Guidance literature:

In water; at 20 ℃; for 24h; Molecular sieve; Green chemistry;

DOI:10.3987/COM-21-14542

Reference yield: 91.0%

2-acetoacetic acid (541-50-4) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 3-hydroxy-3-(2-oxopropyl)indolin-2-one (33417-17-3)

Guidance literature:

In ethyl acetate; at 20 ℃; for 2h; Molecular sieve; Sealed tube;

DOI:10.1016/j.tetlet.2013.06.030

upstream raw materials:

indole-2,3-dione

diethylamine

acetone

3-(2-oxopropyl)-3-tert-butyldimethylsilyl-oxyindolin-2-one

Downstream raw materials:

(S)-3-hydroxy-3-((R)-2'-oxocyclohexyl)indolin-2-one

(R)-3-hydroxy-3-((S)-2'-oxocyclohexyl)indolin-2-one

C₂₆H₂₁N₃O₃

1-(4-Chloro-benzoyl)-3-imidazol-1-yl-3-(2-oxo-propyl)-1,3-dihydro-indol-2-one

Refernces

• 1、 Fernandes, Patricia D.,Zardo, Renata S.,Figueiredo, Gabriella S.M.,Silva, Brbara V.,Pinto, Angelo C.. "Anti-inflammatory properties of convolutamydine A and two structural analogues". . p. 16 - 24. Retrieved 2014.
• 2、 Gupta, Naveen,Tak, Rajkumar,Nazish, Mohd,Jakhar, Ajay,Khan, Noor-ul H.,Kureshy, Rukhsana I.. "Copper(II) Triflate Catalyzed Regioselective and Enantioselective Propargylation of Isatin Derivatives by Using Allenylboronic Acid Pinacol Ester". . p. 1384 - 1392. Retrieved 2018.
• 3、 Banina, Olga A.,Frolova, Larisa L.,Kutchin, Alexander V.,Nigmatov, Albert G.,Sudarikov, Denis V.,Zlotin, Sergei G.. "Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols". . p. 147 - 149. Retrieved 2020.
• 4、 Fujii, Kazuki,Mandai, Hiroki,Mitsudo, Koichi,Shiomoto, Ryuhei,Suga, Seiji. "Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles". supporting information. p. 1169 - 1174. Retrieved 2021/01/13.
• 5、 Tseke, Kavnen,Lennon, Claire,O'Mahony, Joseph,Kinsella, Michael. "A Continuous-Flow Route to Enantioenriched 3-Substituted-3-Hydroxyoxindoles: Organocatalytic Aldol Reactions of Isatin with Acetone". . p. 5767 - 5774. Retrieved 2021/09/18.