394738-76-2

Basic information

• Product Name: (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)
• CAS NO: 394738-76-2
• Molecular Weight: 510.635
• Mol File: 394738-76-2.mol

Chemical Properties

• CAS DataBase Reference: (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)(394738-76-2)
• EPA Substance Registry System: (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)(394738-76-2)

Safety Data

• Hazardous Substances Data: 394738-76-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) is utilized as a building block in organic synthesis for the creation of new compounds with potential applications in various fields. Its unique structure allows for the development of novel chemical entities with improved properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) is employed as a key intermediate in the synthesis of bioactive compounds. Its distinctive chemical structure contributes to the development of new drugs with potential therapeutic benefits.
Used in Materials Science:
(3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) is also used in materials science for the development of advanced materials with unique properties. Its incorporation into material systems can lead to the creation of innovative products with enhanced performance characteristics.

Upstream product

• 100-39-0 benzyl bromide 
• 175166-49-1 [3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] 
• 136030-00-7 (1R,2S)-1-Amino-2-indanol 
• 180186-94-1 bis[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]methane 
• 100-44-7 benzyl chloride 

Relevant articles and documents

Catalytic Asymmetric Fluorination of Copper Carbene Complexes: Preparative Advances and a Mechanistic Rationale

The Cu-catalyzed reaction of substituted α-diazoesters with fluoride gives α-fluoroesters with ee values of up to 95 %, provided that chiral indane-derived bis(oxazoline) ligands are used that carry bulky benzyl substituents at the bridge and moderately bulky isopropyl groups on their core. The apparently homogeneous solution of CsF in C6F6/hexafluoroisopropanol (HFIP) is the best reaction medium, but CsF in the biphasic mixture CH2Cl2/HFIP also provides good results. DFT studies suggest that fluoride initially attacks the Cu- rather than the C-atom of the transient donor/acceptor carbene intermediate. This unusual step is followed by 1,2-fluoride shift; for this migratory insertion to occur, the carbene must rotate about the Cu?C bond to ensure orbital overlap. The directionality of this rotatory movement within the C2-symmetric binding site determines the sense of induction. This model is in excellent accord with the absolute configuration of the resulting product as determined by X-ray diffraction using single crystals of this a priori wax-like material grown by capillary crystallization.

Heterogeneous asymmetric Diels-Alder reactions using a copper-chiral bis(oxazoline) complex immobilized on mesoporous silica

A chiral bis(oxazoline)-copper complex was immobilized onto mesoporous silica and the resulting heterogeneous catalyst was employed in asymmetric Diels-Alder reactions. Reactions using the catalyst exhibited good enantioselectivity of 78% enantiomeric exc

Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions

Chiral bis(oxazolines) are readily dialkylated in the methylene bridge, opening the way to immobilization at that position, keeping the C2 symmetry of the chiral ligand. Bis(oxazolines) functionalized with two allyl or vinylbenzyl groups are easily grafted onto mercaptopropylsilica. Another approach to immobilization is the polymerization of the ligands bearing vinylbenzyl groups to yield insoluble polymers. The Cu(OTf)2 complexes of the immobilized ligands promote the enantioselective cyclopropanation reaction between styrene and ethyl diazoacetate. The results depend on the nature of the support and the method of immobilization. With regard to the type of solid, the best results, which are similar to or even better than those obtained with the corresponding dibenzylated homogeneous catalysts, are obtained with homopolymers. With regard to the bis(oxazoline), that bearing indan groups leads to good results both onto silica and polymers, whereas with the ligand bearing tert-butyl groups good enantioselectivities are only obtained with homopolymeric catalysts. Some of the heterogeneous catalysts can be easily recovered and reused, as much as five times, with the same yield and stereoselectivities.

Polymer-supported Bis(oxazoline)-copper Complexes as Catalysts in Cyclopropanation Reactions

equation presented Bis(oxazolines) are easily immobilized by functionalization of the central methylene bridge with polymerizable groups and subsequent polymerization. Polymers are transformed into copper catalysts active in the cyclopropanation of styrene with ethyl diazoacetate. The results are similar or even better than those obtained with the similar homogeneous systems, and the catalysts can be easily recovered and reused. The substitution in the methylene bridge leads to a slight reduction in the enantioselectivity and an unexpected cis-preference.