(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

Name: (R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one
Brand: ChemScene
Availability: InStock
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CAS No. 191090-32-1
Cat. No. CS-W016717
Molecule weight281.35
Purity≥95%
MDL No.MFCD03093555

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one|CS-W016717

Structure of 191090-32-1

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General Information

CAS No. 191090-32-1
Cat. No. CS-W016717
Purity ≥95%
MDL No. MFCD03093555
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₉NO₂
Molecular Weight 281.35
Synonym(s) (R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
SMILES O=C1OC(C2=CC=CC=C2)([C@@H](C(C)C)N1)C3=CC=CC=C3

Description

(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one is a bench-stable chiral auxiliary featuring a rigid oxazolidinone core flanked by two aryl groups. This configuration enables stereoselective enolate generation and facilitates asymmetric synthesis in complex molecule construction.

Application

(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one serves as a chiral auxiliary in asymmetric synthesis, enabling stereoselective transformations through well-established enantioselective functionalization protocols. Its rigid oxazolidinone framework provides excellent stereocontrol and bench stability, facilitating straightforward purification and compatibility with common reaction conditions. Functions effectively in alkylation, conjugate addition, and metal-catalyzed cross-coupling processes, making it a reliable building block for complex chiral intermediates in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- 443761-68-0
- ~74%
- In-stock
  
  191090-32-1
- 444105-66-2
References
- Organic Process Research and Development, , vol. 8, # 4 p. 597 - 602
Route2
- 649755-76-0
- ~99%
- 649755-77-1
- In-stock
  
  191090-32-1
References
- Organic Process Research and Development, , vol. 8, # 4 p. 597 - 602
Route3
- 223906-36-3
- ~74%
- In-stock
  
  191090-32-1
References
- Bull, Steven D.; Davies, Stephen G.; Jones, Simon; Sanganee, Hitesh J. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 4 p. 387 - 398

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 38.33
LogP 3.6946
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Oxazolidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Chiral compounds Chiral Auxiliaries

Catalysis Asymmetric Synthesis Chiral Auxiliaries

Key Words

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(R)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

CAS No. 191090-32-1

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