7480-28-6

Basic information

• Product Name: 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
• CAS NO: 7480-28-6
• Molecular Weight: 175.187
• Mol File: 7480-28-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one(7480-28-6)
• EPA Substance Registry System: 3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one(7480-28-6)

Safety Data

• Hazardous Substances Data: 7480-28-6(Hazardous Substances Data)

Upstream product

• 128530-88-1 (2,2,2-Trichloro-acetyl)-carbamic acid indan-2-yl ester 
• 4254-29-9 indan-2-ol 
• 51-79-6 urethane 
• 95-13-6 1-indene 
• 442124-77-8 2-indanyl chloroformate 
• 869111-29-5 2,3-dihydro-1H-inden-2-yl hydroxycarbamate 
• 335200-08-3 carbamic acid indan-2-yl ester 

Downstream Products

• 135969-64-1 (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazol-2-one 
• 135969-65-2 (3aR-cis)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one 
• 7480-35-5 (+/-)-cis-1-amino-indan-2-ol 

Relevant articles and documents

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

Synthesis of oxazolidinones: Rhodium-catalyzed C-H amination of: N -mesyloxycarbamates

N-Mesyloxycarbamates undergo intramolecular C-H amination reactions to afford oxazolidinones in good to excellent yields in the presence of rhodium(ii) carboxylate catalysts. The reaction is performed under green conditions and potassium carbonate is used, forming biodegradable potassium mesylate as a reaction by-product. This method enables the production of electron-rich, electron-deficient, aromatic and heteroaromatic oxazolidinones in good to excellent yields. Conformationally restricted cyclic secondary N-mesyloxycarbamates furnish cis-oxazolidinones in high yields and selectivity; DFT calculations are provided to account for the observed selectivity. trans-Oxazolidinones were prepared from acyclic secondary N-mesyloxycarbamates using Rh2(oct)4. The selectivity was reverted with a cytoxazone N-mesyloxycarbamate precursor using large chiral rhodium(ii) carboxylate complexes, affording the corresponding cis-oxazolidinone. This orthogonal selectivity was used to achieve the formal synthesis of (-)-cytoxazone.

A silver-catalyzed intramolecular amidation of saturated C-H bonds

Opportunities with silver: A dinuclear silver(I) compound was found to efficiently catalyze the intramolecular amidation of saturated C-H bonds of carbamates and sulfamates (see scheme). This highly regioselective, stereospecific reaction offers a practical method for the construction of cyclic nitrogen-containing organic molecules.