145631-86-3

Upstream product

• 64-19-7 acetic acid 
• 110-83-8 cyclohexene 
• 79-15-2 N-bromoacetamide 
• 546-67-8 lead(IV) tetraacetate 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 563-63-3 silver(I) acetate 
• 108-22-5 Isopropenyl acetate 
• 2425-33-4 2-bromocyclocyclohexanol 
• 108-05-4 vinyl acetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 127-19-5 N,N-dimethyl acetamide 
• 357-57-3 brucine 
• 108-24-7 acetic anhydride 

Downstream Products

• 874955-58-5 (1R,2S)-2-bromocyclohexanol 
• 14447-34-8 (+)-(R)-cyclohex-2-en-1-yl acetate 
• 3413-44-3 (R)-2-cyclohexen-1-ol 
• 110-83-8 cyclohexene 
• 1759-71-3 trans-1,2-cyclohexanediol diacetate 

Relevant academic research and scientific papers

A simple and facile method for regio- and stereoselective bromoformyloxylation and bromoacetoxylation of olefins using NH4Br and oxone

A mild and efficient protocol for the preparation of bromoformates as well as bromoacetates from olefins using NH4Br and oxone in nucleophile sources (DMF or DMA) without employing catalyst at room temperature is described. This method is facile, environmentally friendly and cost effective. A variety of terminal, internal and cyclic alkenes reacted smoothly to give the corresponding bromoformate and acetate products in good to excellent yields. Moreover, 1,2-disubstituted olefins provided moderate to excellent diastereoselectivity.

Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation.

A simple and efficient bromoformyloxylation and bromoacetoxylation reaction using TsNBr2

Bromoformyloxylation and bromoacetoxylation of olefins proceed smoothly and instantaneously in the presence of N,N-dibromo-p-toluene sulfonamide without any catalyst. The one step reactions can be carried out with all kinds of olefins in high yield and hi

Lipase-catalyzed kinetic resolution of 2-methylene-substituted cycloalkanols in batch and continuous-flow modes

Kinetic resolutions of cyclic racemic secondary alcohols (2-methylenecyclopentan-1-ol rac-1a, 2-methylenecyclohexan-1-ol rac-1b, 2-methylenecycloheptan-1-ol rac-1c, 6-methylene-[1,3]dioxepan-5-ol rac-1d, 2,2-dimethyl-6-methylene-[1,3]dioxepan-5-ol rac-1e and trans-2-bromocyclohexan-1-ol rac-3) catalyzed by different (commercial and in-house-made) lipases were performed using vinyl acetate in THF-hexane. In the most typical cases (rac-1b, rac-1d and rac-3), the immobilized Candida antarctica lipase B (CaLB, for rac-1b and rac-3)- or sol-gel immobilized Pseudomonas fluorescens lipase (sol-gel LAK, for rac-1d)-catalyzed batch mode reactions were compared to the continuous mode reactions carried out in an enzyme-filled stainless steel bioreactor. The effect of temperature (20-60 °C) and flow rate (0.1-0.3 ml min-1) on the continuous-flow acetylation of rac-1b, rac-1d and rac-3 were investigated. In the kinetic resolutions of rac-1b, rac-1d and rac-3, the enantiomeric selectivities (E) were similar in the continuous-flow and batch (shake flask) modes. However, the productivities (specific reaction rate: r), were significantly higher in the continuous-flow mode biotransformations of rac-1b, rac-1d and rac-3.

Iodine(III)-initiated bromoacetoxylation of olefins

A new and mild method for the bromoacetoxylation of olefins is presented, which is initiated by iodine(III). α-Acetoxy bromides 6-11 are generated from olefins 5 in the presence of tetraethylammonium bromide (1) and (diacetoxyiodo)benzene (2). The 1,2-addition to carbohydrate-derived enol ethers results in 2-deoxy-2-bromo-pyranosyl acetates which are versatile glycosyl donors for the synthesis of 2′-deoxy-2′-bromo glycosides 16.

Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

Enantiomerically pure (R)-2-cyclohexen-1-ol 5 was prepared via lipase- catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Diels-Alder reaction and Curtius rearrangement.

Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification

Optically pure (R)-2-cycloalken-1-ols were synthesized via highly enantioselective lipase-catalyzed transesterification of 2-substituted cycloalkanols.

Allylic Oxidation of Olefins by Cobalt(III), Manganese(III), and Cerium(IV) Acetates in Acetic Acid in the Presence of Sodium Bromide

The effect of added sodium bromide on the allylic oxidation of olefins by cobalt(III), manganese(III), and cerium(IV) acetates has been studied.Sodium bromide strongly accelerated the oxidation of cyclohexene by these oxidants to give cyclohex-2-enyl acetate in good yield.Only one product was obtained in the oxidation of cycloalkenes, but two allylic acetates were obtained in the oxidations of methyl-substituted cyclohexenes, which have two kinds of allylic hydrogen.A mechanism involving hydrogen abstraction from allylic sites by bromine radicals is suggested.

CIS 1,2-FUNCTIONALIZATION OF CYCLOHEXANE USING SELENIUM INTERMEDIATES

The trans 1,2-phenylseleno acetate, acetamide, alcohol and nitrile of cyclohexane may be oxidized at selenium by halogens and the phenylseleno moiety displaced by halide to give high yields of 1,2 halide-containing products with cis geometry.