185426-16-8

Basic information

• Product Name: Carbamic acid, [(2R)-2-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester
• CAS NO: 185426-16-8
• Molecular Formula: C13H25NO3
• Molecular Weight: 243.346
• Mol File: 185426-16-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(2R)-2-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(2R)-2-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester(185426-16-8)
• EPA Substance Registry System: Carbamic acid, [(2R)-2-cyclohexyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester(185426-16-8)

Safety Data

• Hazardous Substances Data: 185426-16-8(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 141377-56-2 1-cyclohexyl-2-nitroethanol 
• 3483-39-4 Cyclohexyloxirane 
• 4248-19-5 tert-butyl carbazate 
• 185426-05-5 (1S,2R,1'R)-(-)-N-<2-(1'-cyclohexyl-2'-nitroethoxy)-1-methyl-2-phenylethyl>formamide 
• 50598-92-0 (E)-(2-nitrovinyl)cyclohexane 
• 84619-59-0 (-)-2-cyclohexyl-2-hydroxyethylamine 
• 185426-11-3 (1S,2R,1'R)-(-)-N-<2-(2'-tert-butoxycarbonylamino-1'-cyclohexylethoxy)-1-methyl-2-phenylethyl>formamide 
• 57230-08-7 1-amino-2-cyclohexylethan-2-ol 

Downstream Products

• 1415764-19-0 (S)-N-(2-cyclohexyl-2-hydroxyethyl)-2-iodo-3-methylbenzamide 

Relevant articles and documents

Catalytic enantioselective α-tosyloxylation of ketones using iodoaryloxazoline catalysts: Insights on the stereoinduction process

A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The α-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

Catalytic asymmetric β-peroxidation of nitroalkenes

The first example of an asymmetric β-peroxidation of nitroalkenes is disclosed. The reaction is promoted by catalytic loadings of a commercially available diaryl-2-pyrrolidinemethanol derivative and tert-butyl hydroperoxide as the oxidant. A synthetically useful class of peroxides is obtained in good yield and enantioselectivity (up to 84% ee).

Diastereo- and enantioselective synthesis of vicinal amino alcohols by oxa Michael addition of N-formylnorephedrine to nitro alkenes

The first intermolecular asymmetric oxa Michael additions with removable chirality information within the hydroxide source are reported. As enantiopure oxygen nucleophile functioning as chiral hydroxide equivalent N-formylnorephedrine (7) was used and conjugate additions to aliphatic (E)-nitro alkenes 2a-j were carned out in good yields (35-87%) and excellent diastereomeric excesses (de = 94-≥98%). After reduction of the nitro group and protection of the amino function (11a-h, 73-87%, both steps), the cleavage of the auxiliary occurred without epimerisation (69-99%) using Na/NH3. The Boc-protected 2-amino alcohols 12a-h could be obtained in good overall yields (30-58 %, four steps) and excellent diastereomeric and enantiomeric excesses (de, ee = 94-≥98%). Transition states explaining the overall stereochemical outcome are presented based on the absolute configuration determined by X-ray structure analysis on 8b.