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

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

Uses

Used in Chemical Synthesis:
(-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] is used as a chiral ligand for various chemical reactions, enhancing the selectivity and efficiency of the processes. Its chiral nature allows for the creation of specific enantiomers, which are crucial in the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the preparation of oxazole α-hydroxy esters through intermolecular Alder-Ene reaction, (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] serves as a chiral ligand, enabling the synthesis of biologically active compounds with potential applications in the pharmaceutical industry.
Used in Polymer Science:
(-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] is used as a chiral ligand in the atom transfer radical polymerization reactions of methyl methacrylate. This application allows for the development of polymers with specific properties, such as controlled molecular weight, narrow molecular weight distribution, and well-defined architecture, which are essential for various industrial applications.
Used in Organic Chemistry:
In the copper-catalyzed synthesis of isoxazolidine derivatives by reacting nitrone with α,β-unsaturated acyl phosphonate, (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] acts as a chiral ligand, facilitating the formation of complex organic molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Overall, (-)-2,2'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] is a versatile compound with a wide range of applications in chemical synthesis, pharmaceuticals, polymer science, and organic chemistry, primarily due to its chiral nature and ability to act as a chiral ligand in various reactions.

Upstream product

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

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

Application of a Ritter-type reaction to the synthesis of chiral indane-derived C2-symmetric bis(oxazolines)

Bis(oxazolines) 4, 6, 8, 9, 10, and 11 are prepared in a highly regio- and diastereo-selective manner from dinitriles and indanediol 3 in a Ritter-type reaction initiated by trifluoromethanesulfonic acid.

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.

Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63–98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54–67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.

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

Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram

The enantioselective synthesis of endothelin-A antagonist ABT-546 has been accomplished via the discovery and development of a highly selective catalytic asymmetric conjugate addition of ketoesters to nitroolefins. Employing just 4 mol % bis(oxazoline)-Mg

N-benzylhydroxylamine addition to β-aryl enoates. Enantioselective synthesis of β-aryl-β-amino acid precursors

(matrix presented) Chiral Lewis acid catalyzed N-benzylhydroxylamine addition to pyrrolidinone-derived enoates afforded β-aryl-β-amino acid derivatives in high enantiomeric purity with moderate to very good chemical efficiency.

Conformationally constrained bis(oxazoline) derived chiral catalyst: A highly effective enantioselective Diels-Alder reaction

The reaction of cyclopentadiene with various bidentate dienophiles in the presence of 4-10 mol% of copper(II)-bis(oxazoline) complexes afforded excellent endo/exo selectivity as well as endo enantioselectivity (95-99% ee) and isolated yields. On the other