89869-04-5

Basic information

• Product Name: anti-1-Cyclohexyl-1-benzyloxypent-4-en-2-ol
• CAS NO: 89869-04-5
• Molecular Weight: 274.403
• Mol File: 89869-04-5.mol

Chemical Properties

• CAS DataBase Reference: anti-1-Cyclohexyl-1-benzyloxypent-4-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: anti-1-Cyclohexyl-1-benzyloxypent-4-en-2-ol(89869-04-5)
• EPA Substance Registry System: anti-1-Cyclohexyl-1-benzyloxypent-4-en-2-ol(89869-04-5)

Safety Data

• Hazardous Substances Data: 89869-04-5(Hazardous Substances Data)

Upstream product

• 144222-05-9 1-cyclohexyl-1-(benzyloxy)-2-propene 
• 100-39-0 benzyl bromide 
• 89869-02-3 2-(benzyloxy)-2-cyclohexylacetaldehyde 
• 106-95-6 allyl bromide 
• 762-72-1 allyl-trimethyl-silane 
• 76-63-1 allytriphenyltin 
• 144222-05-9 (+)-[(1-cyclohexylallyloxy)methyl]benzene 
• 141692-80-0 (R)-2-(benzyloxy)-2-cyclohexylacetaldehyde 
• 24850-33-7 allyltributylstanane 

Relevant articles and documents

Indium-catalyzed Barbier allylation reaction

Barbier allylation reaction of carbonyl compounds with allyl bromide was investigated using a catalytic amount of indium (0), indium (I) or indium (III) salts in the presence of a reducer and chlorotrimethylsilane (TMSCl). The Mn/TMSCl couple turned out to be the most efficient system to regenerate active indium in the allylation reaction of various carbonyl compounds including α- and β-oxygenated aldehydes.

CHELATION CONTROL ASSOCIATED WITH ORGANOMETALIC ADDITION REACTION IN WATER. THE HIGH STEREOSELECTIVITY OFFERED BY α- AND β-HYDROXYL SUBSTITUENTS OBVIATES THE NEED FOR PROTECTING GROUPS.

High stereoselectivities have been observed for indium-promoted allylations of α- and β-hydroxy aldehyes in aqueous media, with strong implication that chelate control can continue to operate in water.

Super-acid Catalysed Addition of Allylsilanes to Carbonyl Compounds; Synthetic and Mechanistic Aspects

The addition of allyltrimethylsilane 8 to a variety of aldehydes and one ketone (cyclohexanone) was found to be induced by the super-acid TfOH2(1+)B(OTf)4(1-) (Tf = CF3SO2).In contrast to the analogous Lewis acid catalysed reaction, only catalytic amounts

HIGHLY STEREOSELECTIVE REACTION OF α-METHYLTHIO ALDEHYDES WITH ALLYLTRIPHENYLSTANNANE : SYNTHESIS OF anti-β-METHYLTHIO ALCOHOLS.

The reaction of α-methylthio aldehydes 4 with allyltriphenylstannane 5 in the presence of SnCl4 gave anti-β-methylthio alcohols 6 in excellent selectivity.

STEREOCONTROLLED ADDITIONS OF ALLYLTRI-n-BUTYLSTANNANE TO α-HYDROXYALDEHYDE DERIVATIVES. A USEFUL ROUTE TO MONOPROTECTED ERYTHRO OR THREO DIOLS.

By proper choice of Lewis acid and protecting group, the Lewis acid mediated addition of allyltri-n-butylstannane to the α-hydroxyaldehyde derivatives 1b and 1c can be controlled to give excellent (95: 5 to 250: 1) stereoselectivity for the formation