106928-60-3

Basic information

• Product Name: (+/-)-1-methyl-4r-isopropyl-cyclohexen-⁽¹⁾-ol-(5c)
• CAS NO: 106928-60-3
• Molecular Weight: 154.252
• Mol File: 106928-60-3.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-1-methyl-4r-isopropyl-cyclohexen-⁽¹⁾-ol-(5c)(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-methyl-4r-isopropyl-cyclohexen-⁽¹⁾-ol-(5c)(106928-60-3)
• EPA Substance Registry System: (+/-)-1-methyl-4r-isopropyl-cyclohexen-⁽¹⁾-ol-(5c)(106928-60-3)

Safety Data

• Hazardous Substances Data: 106928-60-3(Hazardous Substances Data)

Upstream product

• 212620-36-5 (R)-(-)-2-isopropyl-5-methylhex-5-enal 
• 264258-71-1 (R)-(+)-2-isopropyl-5-methylhex-5-en-1-ol 
• 317801-61-9 (R)-(+)-2-isopropyl-5-methylhex-5-ene-1-carboxylic acid 
• 317801-57-3 (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone 
• 89-81-6 piperitone 
• 97690-19-2 (+/-)-2-Isopropyl-5-methylhex-5-enal 

Downstream Products

• 490-99-3 DL-neomenthol 

Relevant articles and documents

Asymmetric synthesis and Lewis acid mediated type II carbonyl ene cyclisations of (R)-2-isopropyl-5-methylhex-5-enal

The asymmetric synthesis of (R)-2-isopropyl-5-methylhex-5-enal in 98% ee is described. It was discovered that the key alkylation step employing an Evans chiral auxiliary and 3-methylbut-3-en-1-yl trifluoromethanesulphonate as the alkylating agent led to significant competing O-alkylation, a phenomenon not previously reported. Type II carbonyl ene cyclisation of the aldehyde with a range of Lewis acids led to either the (R,R)- or (R,S)-5-methylidenecyclohexanols without concurrent racemisation of the alpha stereogenic centre of the aldehyde. Conditions for effecting the easy racemisation of a model enantiomerically pure aldehyde, (S)-2-methylbutanal, were developed. In an effort to secure a dynamic kinetic resolution procedure, these conditions were applied to (R)-2-isopropyl-5-methylhex-5-enal. However, a competing and dominant Prins cyclisation occurred instead leading to a mixture of all possible cycloadducts, all of which were obtained in 98% ee. Any unreacted aldehyde was found to be enantiomerically pure. Copyright (C) 2000 Elsevier Science Ltd.

Models for the carbonyl-ene cyclization reaction: Open and closed transition states

Different cyclization products are formed with different Lewis acids in the ene cyclization of 5-hexenals (see scheme on the right; a: methylaluminum bisphenoxide, b: Me2AlCl, c: Sc(OSO2CF3)3). This is not surpr

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.