175166-49-1

Basic information

• Product Name: (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]
• Synonyms: (-)-2,2'-Methylenebis[(3AS,8AR)-3A,8A-Dihydro-8H-Indeno[1,2-D]Oxazole],98%;[3AS-[2(3'A R*,8'A S*),3'A-ALPHA,8'A-ALPHA]]-(-)-2,2'-METHYLENEBIS[3A,8A-DIHYDRO-8 H-INDENO[1,2-D]OXAZOLE];(-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE];[3aS-[2(3′aR*,8′aS*),3′aα,8′aα]]-(−)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole];(-)-2,2'-METHYLENEBIS(3A,8A-DIHYDRO-8H-I NDENO(1,2-D)OXAZOLE), 98%;[3as-[2(3'ar*,8'as*),3'aα,8'aα]]-(-)-2,2'-methylenebis[3a,8a-dihydro-8h-indeno[1,2-d]oxazole];[3as-[2(3′Ar*,8′As*),3′AΑ,8′AΑ]]-()-2,2′-Methylenebis[3a,8a-Dihydro-8H-Inden;[3AS-[2(3'A R*,8'A S*),3'A-ALPHA,8'A-ALPHA]]-(-)-2,2'-METHYLENEBIS[3A,8A-DIHYDRO-8 H-INDENO[1,2-D]OXAZOLE]
• CAS NO: 175166-49-1
• Molecular Formula: C₂₁H₁₈N₂O₂
• Molecular Weight: 330.38
• Product Categories: BOX series;Chiral Nitrogen;Asymmetric Synthesis;Synthetic Organic Chemistry;BOX;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes
• Mol File: 175166-49-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 493.2°Cat760mmHg
• Flash Point: 201.9°C
• Appearance: /
• Density: 1.48g/cm³
• Refractive Index: -360 ° (C=1, CH2Cl2)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: almost transparency in Dichloromethane
• PKA: 5.47±0.20(Predicted)
• CAS DataBase Reference: (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](175166-49-1)
• EPA Substance Registry System: (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](175166-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 175166-49-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

(3aS,3′aS,8aR,8′aR)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] can be used as a chiral ligand:In the preparation of oxazole α-hydroxy esters through intermolecular Alder-Ene reaction.In the atom transfer radical polymerization reactions of methyl methacrylate.In the copper-catalyzed synthesis of isoxazolidine derivatives by reacting nitrone with α,β-unsaturated acyl?phosphonate.

Upstream product

• 142678-92-0 (1R,2S)-amino indanol 
• 4370-02-9 cis-1,2-indandiol 
• 109-77-3 malononitrile 
• 10344-69-1 diethyl malonoimidate dihydrochloride 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 

Downstream Products

• 195703-68-5 (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-diphenylpropane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 2085239-89-8 (3aS,3a'S,8aR,8a'R)-2,2'-(cycloheptane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 1435467-29-0 C₅₁H₆₂N₂O₂ 
• 1435467-28-9 (3aS,3a'S,8aR,8a'R)-2,2'-(1,3-bis(4-(tert-butyl)phenyl)propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 175166-51-5 (3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 229184-98-9 {3aS-[2(3'aR*,8'aS*),3aα,8aα]}-2,2'-(cyclopropylidene)-bis{3a,8a-dihydro-8H-indeno[1,2-d]-oxazole} 

Relevant articles and documents

Reusable chiral bis(oxazoline)-copper complexes immobilized by donor-acceptor interactions on insoluble organic supports

Heterogeneous asymmetric Diels-Alder reactions between cyclopentadiene and 3-but-2-enoyl-oxazolidin-2-one were efficiently promoted by reusable chiral bis(oxazoline)-copper catalysts, immobilized through charge transfer interactions with trinitrofluorenon

CuII/TEMPO-Catalyzed Enantioselective C(sp3)–H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.

Synthetic and theoretical investigations of myrmicarin biosynthesis

Off to a good start: Use of a carefully designed building block coupled with several highly selective reactions has enabled the syntheses of the monomeric myrmicarins (see scheme) and the investigation of higher-order oligomer synthesis by enabling access