348135-81-9

Usage

Physical state

Clear, colorless liquid

Uses

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals; reagent in organic synthesis; precursor to various functionalized organic compounds; crosslinking agent in polymer materials production

Odor

Strong, pungent

Toxicity

Toxic and harmful if swallowed, inhaled, or absorbed through the skin

Safety precautions

Handle and store with appropriate safety measures

Upstream product

• 22516-18-3 3-(cyclohex-1-en-1-yl)propan-1-ol 
• 63715-12-8 1-(3-mesyloxypropyl)-1-cyclohexene 
• 3197-68-0 2-(1-Cyclohexenyl)ethanol 
• 53723-52-7 methyl 1-cyclohexene-1-acetate 
• 60-12-8 2-phenylethanol 
• 6975-71-9 1-cyclohexenylacetonitrile 
• 27338-44-9 3-(cyclohex-1-en-1-yl)propionic acid 
• 13992-92-2 3-(cyclohex-1-en-1-yl)propanenitrile 
• 82201-80-7 1-iodo-2-(1-cyclohexenyl)ethane 
• 136425-21-3 2-(1-cyclohexenyl)ethyl methanesulfonate 
• 18294-87-6 1-cyclohexenylacetic acid 

Downstream Products

• 348135-82-0 1-(5-pentynyl-6-trimethylsilyl)-cyclohexane 
• 1488285-93-3 C₁₉H₂₃NO₂ 
• 389607-99-2 5-(1-cyclohexenyl)-pentanophenone 
• 389607-98-1 5-(1-cyclohexenyl)-pentanophenone N,N-dimethylhydrazone 

Relevant academic research and scientific papers

Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: Discovery of deleobuvir (BI 207127)

Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: Evaluation of C- versus O-alkylation process

The intramolecular addition reaction of metal enolates of ketones to oxiranes has been applied to a series of epoxy ketones derived from cyclohexene oxide. γ-Hydroxy ketones (γ-HKs, C-alkylation products) or hydroxy enol ethers (HEEs, O-alkylation products) are obtained, depending on the nature of the cyclic transition state in each case involved and the application of the Fu?rst-Plattner rule. The formation of HEEs by reaction of the same epoxy ketones under acid conditions is also described. In some cases, regioconvergent or chemoselective processes are conveniently obtained.

Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson-Khand reaction of exo- and endo-cyclic enynes

Intramolecular Pauson-Khand reaction of various alkynyl exo-alkylidene-cyclohexanes and -pentane gives angular type 6-5-5 and 5-5-5 tricyclic compounds in good to high yield. The present reaction also offers convenient construction of two contiguous quaternary centers, which could not be synthesized from alkynyl endo-cycloolefins. Scope and limitation of the present reaction of various exo- and endo-cyclic enynes are also described.