180186-94-1

Basic information

• Product Name: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]
• Synonyms: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE];[3ar-[2(3'ar*,8'as*),3'aβ,8'aβ]]-(+)-2,2'-methylenebis[3a,8a-dihydro-8h-indeno[1,2-]oxazole];(-)-2,2''-METHYLENEBIS-[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] EP;[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a;(3aR,3'aR,8aS,8'aS)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole];[3aR-[2(3'aR*,8'aS*),3'aβ,8'aβ]]-(+)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole];Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)Methane;[3aR-[2(3
• CAS NO: 180186-94-1
• Molecular Formula: C₂₁H₁₈N₂O₂
• Molecular Weight: 330.38
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry;BOX;Chiral Catalysts, Ligands, and Reagents;Privileged Ligands and Complexes;BOX series;Chiral Nitrogen
• Mol File: 180186-94-1.mol

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 493.2°Cat760mmHg
• Flash Point: 201.9°C
• Appearance: /
• Density: 1.48
• Refractive Index: 360 ° (C=1, CH2Cl2)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.47±0.20(Predicted)
• CAS DataBase Reference: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](CAS DataBase Reference)
• NIST Chemistry Reference: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](180186-94-1)
• EPA Substance Registry System: (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE](180186-94-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 180186-94-1(Hazardous Substances Data)

Usage

Uses

Used in Enantioselective Catalysis:
(+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] is used as a chiral ligand in enantioselective catalysis for its ability to form bidentate coordination complexes with metals, enhancing the selectivity and efficiency of chemical reactions.
Used in Cyclopropanation Reactions:
In the Chemical Industry, (+)-2,2'-METHYLENEBIS[(3AR,8AS)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE] is used as a catalyst component in the cyclopropanation reaction between styrene and ethyl diazoacetate. Its copper complex serves as a reusable catalyst, improving the sustainability and cost-effectiveness of the process.

Upstream product

• 136030-00-7 (1R,2S)-1-Amino-2-indanol 
• 10344-69-1 diethyl malonoimidate dihydrochloride 

Downstream Products

• 394738-76-2 C₃₅H₃₀N₂O₂ 
• 319489-97-9 [3aR-[2(3'aR*,8'aS*),3'aα,8'aα]]-2,2'-[1,3-di(p-vinylphenyl)isopropylidene]bis[3a,8a-dihydro-8H-indeno(1,2-d)oxazole] 
• 175166-51-5 (1R,2S)-Inda-Box 
• 950596-31-3 1,1-bis[(4R,5S)-4,5-indanediyloxazolin-2-yl]ethane 
• 229184-98-9 (3aR,3'aR,8aS,8'aS)-2,2'-cyclopropylidenebis-[3a,8a]-dihydro-8H-indeno-[1,2-d]oxazole 
• 1374295-27-8 5,5-bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)nonane-1,9-ditosylate 
• 2085239-89-8 (3aR,3a'R,8aS,8a'S)-2,2'-(cycloheptane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 2005443-90-1 (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopentane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 
• 2182671-16-3 C₄₃H₄₆N₂O₂ 

Relevant articles and documents

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

Cu-catalyzed enantioselective alkylarylation of vinylarenes enabled by chiral binaphthyl-box hybrid ligands

Transition-metal-catalyzed radical relay coupling reactions have recently emerged as one of the most powerful methods to achieve difunctionalization of olefins. However, there has been limited success in applying this method to asymmetric catalysis using an effective chiral ligand. Herein we report the Cu-catalyzed enantioselective alkylarylation of vinylarenes using alkylsilyl peroxides as alkyl radical sources. This reaction proceeds under practical reaction conditions and affords chiral 1,1-diarylalkane structures that are found in a variety of bioactive molecules. Notably, a highly enantioselective reaction was accomplished by combining chiral bis(oxazoline) ligands with chiral binaphthyl scaffolds.

Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling

An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.

Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.

A new method for recycling asymmetric catalysts via formation of charge transfer complexes

A new concept for recycling asymmetric bis(oxazoline)-type catalysts is reported. The formation of charge-transfer complexes between the chiral ligand and trinitrofluorenone and their subsequent precipitation and reuse by addition of new substrate solutions is described. The efficiency of this procedure is demonstrated in a Diels-Alder reaction to reach the expected endo product as major isomer (up to 97% de and 94% ee): the catalyst was used up to 12 times without loss of either activity or selectivity.

METHOD OF PREPARING A RING COMPOUND HAVING TWO ADJACENT CHIRAL CENTERS

A method of synthesizing a chiral compound having a quarternary carbon atom bearing diastereotopic groups from (a) a nitroolefin and (b) an α-substituted β-dicarbonyl or an equivalent compound having an acidic C-H moiety compound is disclosed. A subsequen

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