20180-54-5

Basic information

• Product Name: 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol
• Synonyms: 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol
• CAS NO: 20180-54-5
• Molecular Weight: 224.343
• Mol File: 20180-54-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol(20180-54-5)
• EPA Substance Registry System: 1-[(E)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol(20180-54-5)

Safety Data

• Hazardous Substances Data: 20180-54-5(Hazardous Substances Data)

Upstream product

• 23528-44-1 1,2-bis-(phenylmercapto)ethylene 
• 108-94-1 cyclohexanone 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 

Downstream Products

• 53723-48-1 1,1'-(1,2-ethanediylidene)biscyclohexane 
• 33493-94-6 1-[(E)-2-(1-Methoxy-cyclohexyl)-vinyl]-cyclohexanol 

Relevant articles and documents

DTBB-catalysed lithiation of 1,2-bis(phenylsulfanyl)ethene: Does 1-lithio-2-phenylsulfanylethene really exist?

The reaction of (Z)- or (E)-1,2-bis(phenylsulfanyl)ethene (1) with an excess of lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 2.5 mol%) in the presence of a carbonyl compound as electrophile (Barbier conditions) in THF at -78°C leads, after hydrolysis with water at temperatures ranging between -78°C and rt, to a mixture of the corresponding (Z/E)-unsaturated 1,4-diols 2, the diastereomers ratio being independent of the stereochemistry of the starting materials. Allylic alcohols 3 are the main by-products, resulting from a lithium-hydrogen exchange on some of the lithiated intermediates along the whole process. A mechanistic explanation for the observed behaviour is given.