57770-11-3

Usage

Uses

Used in Organic Synthesis:
1-(azidomethyl)cyclohexan-1-ol is used as a building block in organic synthesis for its ability to contribute to the creation of complex organic molecules with potential pharmaceutical and biological activities.
Used in Medicinal Chemistry and Drug Development:
In the field of medicinal chemistry and drug development, 1-(azidomethyl)cyclohexan-1-ol is used as a key intermediate for synthesizing compounds with potential therapeutic applications, leveraging its unique cyclohexane ring and azide group to form novel molecular structures.
Used in Chemical Reactions:
1-(azidomethyl)cyclohexan-1-ol is utilized as a reactant in various chemical reactions, taking advantage of its reactive azide group to form new bonds and functional groups in target molecules.

Upstream product

• 1192-37-6 methylenecyclohexane 
• 185-70-6 1-oxaspiro(2.5)octane 
• 108-94-1 cyclohexanone 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 502-42-1 cycloheptanone 

Relevant academic research and scientific papers

Catalytic activity of halohydrin dehalogenases towards spiroepoxides

A novel activity of halohydrin dehalogenases towards spiroepoxides has been found. The enzyme from Arthrobacter sp. (HheA) catalysed highly regioselective azidolysis of spiroepoxides containing 5, 6 and 7-membered cycloalkane rings, while the enzyme from Agrobacterium radiobacter (HheC), besides high regioselectivity, also displayed moderate to high enantioselectivity (E up to >200) that can be applied for the kinetic resolution of chiral spiroepoxides. The orientations of spiroepoxides in the active site of halohydrin dehalogenases were studied by quantum-chemical calculations and docking simulations. Analyses of the complexes obtained revealed the origins of diastereoselectivity and enantioselectivity of the investigated biotransformations.

A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

Under solvent-free conditions the reaction of epoxides 1a-i with trimethylsilylazide (2) catalyzed by polystiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a-i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a-i in excellent yields (83-99% and 82-96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al2O3/HCOOH system.

An Efficient Nucleophilic Cleavage of Oxiranes to 1,2-Azido Alcohols

Regioselective ring opening of oxiranes has been induced by the SnCl2·2H2O-Mg-THF/NaN3-H2O system to give the corresponding 1,2-azido alcohols in good yields.

Efficient metal salt catalyzed azidolysis of epoxides with sodium azide in acetonitrile

A new, simple, efficient, completely anti stereoselective method for the azidolysis of 1,2 epoxides with NaN3 in acetonitrile, by means of metal salts, is described. The use of a non-protic solvent makes this method very competitive with the ot

HIGHLY NUCLEOPHILIC TRIBUTYLTIN AZIDE IN OXIRANE RING CLEAVAGE LEADING TO 1,2-AZIDO ALCOHOL

Enhanced reactivity of tributyltin azide has been demonstrated in nucleophilic ring cleavage of oxiranes without solvent and promoter to give 1,2-azido alcohols in good to excellent yields.