2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine

Base Information

• Chemical Name: 2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine
• CAS No.: 357209-32-6
• Molecular Formula: C₂₅H₁₉N₃O₂
• Molecular Weight: 393.445
• Hs Code.: 29349990
• European Community (EC) Number: 693-025-7
• DSSTox Substance ID: DTXSID20479118
• Nikkaji Number: J1.803.156F
• Wikidata: Q72446069
• Mol file: 357209-32-6.mol

Synonyms:357209-32-6;2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine;2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine;(3aR,8aS)-in-pybox;2,6-BIS[(3AR,8AS)-(+)-8H-INDENO[1,2-D]OXAZOLIN-2-YL]PYRIDINE;(3aS,8bR)-2-[6-[(3aS,8bR)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]pyridin-2-yl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole;2,6-bis((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)pyridine;MFCD09265074;(R,S)-In-Pybox;DTXSID20479118;26-Bis[(3aR8aS)-(+)-8H-indeno[12-d]oxazolin-2-yl)pyridine;NSC819326;AKOS016843569;NSC-819326;BS-22816;CS-0035259;D82311;2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine, >=94%;(3aR,3'aR,8aS,8'aS)-2,2'-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole], 98% (99% ee)

Chemical Property of 2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 3.05E-15mmHg at 25°C
• Melting Point: 284 °C (dec.)
• Refractive Index: 1.797
• Boiling Point: 633 °C at 760 mmHg
• PKA: 4.35±0.20(Predicted)
• Flash Point: 336.6 °C
• PSA: 56.07000
• Density: 1.5 g/cm³
• LogP: 2.83840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 393.147726857
• Heavy Atom Count: 30
• Complexity: 691

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3aR,3'aR,8aS,8'aS)-2,2'-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole], 98% (99% ee) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C3=CC=CC=C31)N=C(O2)C4=NC(=CC=C4)C5=NC6C(O5)CC7=CC=CC=C67
• Isomeric SMILES: C1[C@H]2[C@@H](C3=CC=CC=C31)N=C(O2)C4=NC(=CC=C4)C5=N[C@H]6[C@@H](O5)CC7=CC=CC=C67
• Uses: Catalytic ligand used for:[3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavageEnantioselective Mukaiyama-aldol reactionsEnantioselective carbonyl-ene reactionsCu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynesAsymmetric three-component coupling reactions catalyzed by a Cu/pybox complexEnantioselective Diels-Alder reactionNi-catalyzed cross-coupling reactions

Technology Process of 2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine

There total 8 articles about 2,6-Bis((3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

pyridine-2,6-dinitrile (2893-33-6) + (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → 2,6-bis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine (185346-09-2,357209-32-6)

Guidance literature:

pyridine-2,6-dinitrile; With sodium; In methanol; for 48h; Inert atmosphere;

(1S,2R)-1-amino-2-indanol; In dichloromethane; at 40 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201105739

Reference yield: 85.0%

pyridine-2,6-dinitrile (2893-33-6) + (1R,2S)-1-Amino-2-indanol (136030-00-7) → 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine (357209-32-6)

Guidance literature:

With zinc trifluoromethanesulfonate; In toluene; for 48h; Heating;

DOI:10.1055/s-2005-872672

Reference yield: 73.0%

Pyridine-2,6-dicarboxylic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide] → 2,6-bis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine (185346-09-2,357209-32-6)

Guidance literature:

With boron trifluoride diethyl etherate; at 120 ℃; for 6h;

DOI:10.1021/jo9616264

upstream raw materials:

pyridine-2,6-dicarboximidic acid dimethyl ester

(1S,2R)-1-amino-2-indanol

2,6-Pyridinedicarbonyl dichloride

pyridine-2,6-dinitrile

Refernces

• 1、 Gutierrez, Elisa G.,Wong, Casey J.,Sahin, Aziza H.,Franz, Annaliese K.. "Enantioselective and regioselective indium(III)-catalyzed addition of pyrroles to isatins". supporting information; experimental part. p. 5754 - 5757. Retrieved 2011/12/05.
• 2、 Cornejo,Fraile,García,Gil,Martínez-Merino,Mayoral,Pires,Villalba. "An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands". . p. 2321 - 2324. Retrieved 2007/10/03.