1190284-95-7

Basic information

• Product Name: (S)-3-allyl-1-benzyl-3-hydroxyindolin-2-one
• Synonyms: (S)-3-allyl-1-benzyl-3-hydroxyindolin-2-one
• CAS NO: 1190284-95-7
• Molecular Weight: 279.338
• Mol File: 1190284-95-7.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (S)-3-allyl-1-benzyl-3-hydroxyindolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-allyl-1-benzyl-3-hydroxyindolin-2-one(1190284-95-7)
• EPA Substance Registry System: (S)-3-allyl-1-benzyl-3-hydroxyindolin-2-one(1190284-95-7)

Safety Data

• Hazardous Substances Data: 1190284-95-7(Hazardous Substances Data)

Upstream product

• 591-87-7 Allyl acetate 
• 1217-89-6 1-benzylisatin 
• 461677-71-4 1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one 
• 97-72-3 2-Methylpropionic anhydride 
• 91-56-5 indole-2,3-dione 
• 100-39-0 benzyl bromide 
• 74348-96-2 2-(prop-2-en-1-yl)-1,3,2-dioxaborolane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 51851-79-7 diisopropyl allylboronate 
• 54655-41-3 B-allyl-1,3,2-dioxaborinane 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 762-72-1 allyl-trimethyl-silane 
• 7393-43-3 tetraallyl tin 

Relevant articles and documents

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.

BINOL derivatives-catalysed enantioselective allylboration of isatins: Application to the synthesis of (: R)-chimonamidine

The asymmetric synthesis of the 3-allyl-3-hydroxyoxindole skeleton was accomplished in yields up to 99% via a metal-free and enantioselective allylation of isatins (90-96% ee) using BINOL derivatives as catalysts and an optimized allylboronate. This methodology was applied at a gram-scale to the synthesis of the natural product (R)-chimonamidine. This journal is

Evaluating polymer-supported isothiourea catalysis in industrially-preferable solvents for the acylative kinetic resolution of secondary and tertiary heterocyclic alcohols in batch and flow

Polymer-supported Lewis base catalysts, based on the homogeneous isothioureas HyperBTM and BTM, have been synthesised and applied for the acylative kinetic resolution of secondary and tertiary heterocyclic alcohols. In batch, the use of industrially-preferable solvents was investigated, with dimethyl carbonate proving to be most generally-applicable. Significantly, the HyperBTM-derived immobilised catalysts were readily recycled, with no loss in either activity or selectivity. In addition to the kinetic resolution of secondary benzylic, propargylic, allylic and cycloalkanol derivatives, a range of 22 tertiary heterocyclic alcohols, based on privileged 3-hydroxyoxindole and 3-hydroxypyrrolidinone substructures, were resolved with up to excellent selectivity (s = 7-190). Finally, the immobilised isothiourea catalysts were applied in a packed bed reactor to demonstrate the first example of the kinetic resolution of tertiary heterocyclic alcohols in a continuous flow process. High selectivities were obtained for the resolution of 3-hydroxyoxindole derivatives in ethyl acetate (s up to 70); and for 3-hydroxypyrrolidinones derivatives in toluene (s up to 42).