144300-25-4

Basic information

• Product Name: (1R,2R)-1-acetoxy-2-iodocyclohexane
• Synonyms: (1R,2R)-1-acetoxy-2-iodocyclohexane
• CAS NO: 144300-25-4
• Molecular Weight: 268.095
• Mol File: 144300-25-4.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: (1R,2R)-1-acetoxy-2-iodocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-1-acetoxy-2-iodocyclohexane(144300-25-4)
• EPA Substance Registry System: (1R,2R)-1-acetoxy-2-iodocyclohexane(144300-25-4)

Safety Data

• Hazardous Substances Data: 144300-25-4(Hazardous Substances Data)

Upstream product

• 110-82-7 cyclohexane 
• 563-63-3 silver(I) acetate 
• 543-90-8 cadmium(II) acetate 
• 110-83-8 cyclohexene 
• 631-61-8 ammonium acetate 
• 64-19-7 acetic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-24-7 acetic anhydride 
• 626-62-0 Cyclohexyl iodide 
• 301-04-2 lead acetate 
• 22306-37-2 bismuth(III) acetate 
• 546-67-8 lead(IV) tetraacetate 
• 127-08-2 potassium acetate 
• 1600-27-7 mercury(II) diacetate 

Downstream Products

• 14447-34-8 (+)-(R)-cyclohex-2-en-1-yl acetate 
• 1792-81-0 cis-1,2-cyclohexane 
• 116051-21-9 (1R,2R)-trans-2-iodo-cyclohexanol 
• 2396-76-1 cis-1,2-diacetoxycyclohexane 
• 1759-71-3 trans-1,2-cyclohexanediol diacetate 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 93-92-5 1-phenylethyl acetate 
• 86703-56-2 cis-1-acetoxycyclohexane-2-ol 
• 10039-14-2 2-iodo-1-cyclohexanol 
• 133715-11-4 ((3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthen-11-yl)-carbamic acid benzyl ester 
• 133715-24-9 (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate 
• 1027905-47-0 (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide 
• 133775-36-7 <3aR-(3aα,12α,12aα,12bα)>-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-2(1H)-one hydrochloride 
• 3413-44-3 (R)-2-cyclohexen-1-ol 

Relevant articles and documents

Sulfonium Salts of Iodine(I) Species as Efficient Reagents for the Regioselective Bisfunctionalisation of Glycals and Enol Ethers

A new sulfonium-salt-based iodine(I) reagent system for the vicinal functionalisation of glycals and enol ethers has been developed. The unprecedented iodine(I) complex, Me3SI(OAc)2, generated in situ from Me3SI and PhI(OAc)2, effectively promoted the one-pot iodocarboxylation using carboxylic acids, and iodoazidation using NaN3 or TMSN3 (trimethylsilyl azide). The scope and generality of the new reagent was probed for a wide range of substrates, including various substituted aromatic carboxylic acids, heterocyclic, alicyclic, and aliphatic carboxylic acids, and amino acids to obtain various functionalised glycoconjugates in high yields (99 %) and with diastereoselectivities up to 100 %. A new sulfonium-salt-based iodine(I) reagent system has been developed for the vicinal functionalisation of glycals and enol ethers. The unprecedented iodine(I) complex generated in situ from Me3SI and PhI(OAc)2 effectively promoted iodocarboxylation and iodoazidation reactions in excellent yields and with diastereoselectivities up to 100 %.

Enzymatic resolution of stereoisomers of 2-iodocyclohexanol

All four optically active stereoisomers of 2-iodocyclohexanol were synthesized. Their enantiomeric purity was determined upon derivatization with Mosher's acid, absolute configuration have been established by chemical correlation.

Triiodoisocyanuric acid: a new and convenient reagent for regioselective coiodination of alkenes and enolethers with oxygenated nucleophiles

The reaction of triiodoisocyanuric acid (prepared from I2 and trichloroisocyanuric acid in 90% yield) with alkenes in the presence of oxygenated nucleophilic solvents (alcohols, AcOH and H2O) led to the corresponding β-iodoethers, β-iodoacetates and iodohydrins, in 66-98% isolated yield. Enolethers reacted with triiodoisocyanuric acid in MeOH to produce dialkylacetals (70-83%).