(S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Base Information

• Chemical Name: (S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
• CAS No.: 463941-07-3
• Molecular Formula: C24H24BNO
• Molecular Weight: 353.272
• DSSTox Substance ID: DTXSID90458596
• Nikkaji Number: J1.726.351J
• Wikidata: Q82282021
• Mol file: 463941-07-3.mol

Synonyms:463941-07-3;(S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;(3aS)-1-(2-methylphenyl)-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;(S)-(-)-o-Tolyl-CBS-oxazaborolidine;SCHEMBL15481290;DTXSID90458596;(5S)-2-(2-Methylphenyl)-4,4-diphenyl-1-aza-2-bora-3-oxabicyclo[3.3.0]octane

Chemical Property of (S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Chemical Property:

• Vapor Pressure: 3.96E-09mmHg at 25°C
• Refractive Index: n20/D 1.514
• Boiling Point: 473.3ºC at 760 mmHg
• PKA: -0.32±0.40(Predicted)
• Flash Point: 7ºC
• PSA: 12.47000
• Density: 0.9009 g/mL at 25ºC
• LogP: 4.06650
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 353.1950946
• Heavy Atom Count: 27
• Complexity: 481

Purity/Quality:

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

(S)?-?(-?)?-?o-?Tolyl-?CBS-?oxazaborolidine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62-16

MSDS Files:

Useful:

• Canonical SMILES: B1(N2CCCC2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5C
• Isomeric SMILES: B1(N2CCC[C@H]2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5C
• Uses: (S)?-?(-?)?-?o-?Tolyl-?CBS-?oxazaborolidine is a chiral catalyst used in the organic reactions such as enantioselective diels-alder reactions.

Technology Process of (S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

There total 4 articles about (S)-3,3-Diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c][1,3,2]oxazaborole 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:

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + tri-o-tolylboroxine (7294-50-0) → (S)-3,3-diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c]-[1,3,2]oxazaborole (463941-07-3,865812-10-8)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1021/ja035393r DOI:10.1021/ja049323b DOI:10.1021/ja068637r

Reference yield:

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + 2-Methylphenylboronic acid (16419-60-6) → (S)-3,3-diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c]-[1,3,2]oxazaborole (463941-07-3,865812-10-8)

Guidance literature:

In toluene; Reflux;

DOI:10.1021/ol902280d

Reference yield:

dibromo(o-tolyl)borane (156629-31-1) + (S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) → (S)-3,3-diphenyl-1-(o-tolyl)hexahydropyrrolo[1,2-c]-[1,3,2]oxazaborole (463941-07-3,865812-10-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In benzene; at 20 - 40 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ol902865d

upstream raw materials:

(S)-diphenylprolinol

tri-o-tolylboroxine

2-Methylphenylboronic acid

dibromo(o-tolyl)borane