3-hydroxy-3-(2-oxocyclohexyl)-1,3-dihydro-2H-indol-2-one

Base Information

• Chemical Name: 3-hydroxy-3-(2-oxocyclohexyl)-1,3-dihydro-2H-indol-2-one
• CAS No.: 76325-79-6
• Molecular Formula: C14H15 N O3
• Molecular Weight: 245.278
• Mol file: 76325-79-6.mol

Synonyms:2-Indolinone,3-hydroxy-3-(2-oxocyclohexyl)- (7CI); NSC 234305

Chemical Property of 3-hydroxy-3-(2-oxocyclohexyl)-1,3-dihydro-2H-indol-2-one

Chemical Property:

• Vapor Pressure: 7.13E-11mmHg at 25°C
• Boiling Point: 501.4°C at 760 mmHg
• Flash Point: 257°C
• Density: 1.339g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-hydroxy-3-(2-oxocyclohexyl)-1,3-dihydro-2H-indol-2-one

There total 8 articles about 3-hydroxy-3-(2-oxocyclohexyl)-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:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (S)-3-hydroxy-3-((R)-2'-oxocyclohexyl)indolin-2-one (1221577-88-3) + (R)-3-hydroxy-3-((S)-2'-oxocyclohexyl)indolin-2-one (1228658-39-6) + 3-hydroxy-3-(2-oxocyclohexyl)-2-indolinone (76325-79-6)

Guidance literature:

With (S)-2-amino-N-(anthracene-1-yl)-3,3-dimethylbutan-amide; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 20h; Reagent/catalyst; Solvent; Temperature; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1002/ejoc.201600414

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 3-hydroxy-3-(2-oxocyclohexyl)indolin-2-one (76325-79-6) + (S)-3-hydroxy-3-((R)-2'-oxocyclohexyl)indolin-2-one (1221577-88-3) + (R)-3-hydroxy-3-((S)-2'-oxocyclohexyl)indolin-2-one (1228658-39-6)

Guidance literature:

With (2S)-(1,2,4-triazol-3-yl)proline supported on mesoporous silica; In neat (no solvent); at 1 ℃; for 10h; Overall yield = 88 percent;

DOI:10.3390/molecules25194532

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (rel)-(S)-3-hydroxy-3-[(S)-2-oxocyclohexyl]indolin-2-one (76325-79-6) + (SR)-3-hydroxy-3-[(RS)-2-oxocyclohexyl]indolin-2-one

Guidance literature:

With C₁₉H₂₂N₂; trifluoroacetic acid; In toluene; at 20 ℃; for 24h; Overall yield = 46 %; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2016.08.013

upstream raw materials:

indole-2,3-dione

cyclohexanone

Downstream raw materials:

trans-3-(2-hydroxycyclohexyl)-indole

cis-3-(2-hydroxycyclohexyl)-indole

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

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

Refernces

• 1、 Cruz-Hernández, Carlos,Hernández-González, Perla E.,Juaristi, Eusebio. "(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organo catalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water". supporting information. p. 1827 - 1840. Retrieved 2018/02/14.
• 2、 Ogasawara, Ayumi,Subba Reddy,Seki, Chigusa,Okuyama, Yuko,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto. "2-Azanorbornane-based amine organocatalyst for enantioselective aldol reaction of isatins with ketones". . p. 1062 - 1068. Retrieved 2016/10/11.