3645-01-0

Basic information

• Product Name: Cyclohexane, (1-methyl-2-propenyl)-
• CAS NO: 3645-01-0
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• Mol File: 3645-01-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Cyclohexane, (1-methyl-2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexane, (1-methyl-2-propenyl)-(3645-01-0)
• EPA Substance Registry System: Cyclohexane, (1-methyl-2-propenyl)-(3645-01-0)

Safety Data

• Hazardous Substances Data: 3645-01-0(Hazardous Substances Data)

Upstream product

• 109-71-7 3-chloro-1-iodo-1-propyne 
• 1568-65-6 bis(cyclohexanyl)borane 
• 917-54-4 methyllithium 
• 917-64-6 methyl magnesium iodide 
• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 372-46-3 fluorocyclohexane 
• 3536-96-7 vinylmagnesium chloride 
• 626-62-0 Cyclohexyl iodide 
• 103185-13-3 (E)-crotyl methyl carbonate 
• 108-85-0 1-bromocyclohexane 
• 7204-29-7 trans-2-butenyl acetate 
• 32399-81-8 2-cyclohexyl-1,3-butadiene 
• 931-50-0 cyclohexylmagnesium bromide 
• 931-51-1 cyclohexylmagnesiumchloride 

Relevant articles and documents

The Hydroboration of 3-Chloro-1-iodo-1-propyne with Dialkylboranes, and its Application to the Syntheses of Some Geminally Dialkylated Propene Derivatives

3-Chloro-1-iodo-1-propyne is smoothly hydroborated with dialkylboranes, giving (Z)-(3-chloro-1-iodo-1-propenyl)dialkylboranes exclusively.Subsequent treatment of the hydroboration mixture with sodium methoxide or aqueous sodium hydroxide results in migration of two alkyl groups from the boron atom to the α-alkenyl carbon atom to provide dialkylated allylboranes, which are protonolyzed with methanol or water to produce 1,1-dialkyl-1-propenes.Oxidation of the allylboranes with alkaline hydrogen peroxide prior to protonolysis gives 1,1-dialkyl-2-propen-1-ols.Treatmentof (Z)-(3-chloro-1-iodo-1-propenyl)dicyclohexylborane with Grignard reagents, followed by protonolysis with acetic acid, provides 3-alkyl-3-cyclohexyl-1-propenes in which the alkyl group is derived from Grignard reagent.

Copper catalyzed magnesium-Barbier reaction for γ-selective alkyl-allyl coupling

CuCN catalyzed alkyl-allyl coupling under magnesium-Barbier conditions occurs regioselectively and affords predominantly the γ-products in good to high yields. This one-pot CuCN catalyzed reaction utilising Mg, an alkyl halide and an allylic substrate in THF at room temperature provides an easy alternative to the classical CuCN catalyzed γ-allylation of alkyl Grignard reagents.

Enantioselective copper-mediated allylic substitution with Grignard reagents employing a chiral reagent-directing leaving group

Enantioselective copper-mediated allylic substitution with Grignard reagents was achieved employing the ortho-diphenylphosphanylferrocene carboxylate (o-DPPF) system as a planar chiral reagent-directing leaving group. Careful optimization of reaction parameters resulted in excellent regioselectivities and enantioselectivies of up to 95% ee.