141033-67-2

Basic information

• Product Name: (1RS,2RS)-1-(4',4'-dimethyl-3'-methylidenecyclohex-1-enyl)propane-1,2-diol
• CAS NO: 141033-67-2
• Molecular Weight: 196.29
• Mol File: 141033-67-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1RS,2RS)-1-(4',4'-dimethyl-3'-methylidenecyclohex-1-enyl)propane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1RS,2RS)-1-(4',4'-dimethyl-3'-methylidenecyclohex-1-enyl)propane-1,2-diol(141033-67-2)
• EPA Substance Registry System: (1RS,2RS)-1-(4',4'-dimethyl-3'-methylidenecyclohex-1-enyl)propane-1,2-diol(141033-67-2)

Safety Data

• Hazardous Substances Data: 141033-67-2(Hazardous Substances Data)

Upstream product

• 141033-65-0 (S)-2,2-Dimethyl-5-((2S,3R)-3-methyl-oxiranyl)-cyclohexanone 
• 67-68-5 dimethyl sulfoxide 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 77-76-9 2,2-dimethoxy-propane 

Relevant articles and documents

Investigations Concerning an Unexpected Reaction between the Dimsyl Anion (= (Methylsulfinyl)methanide) and a γ,δ-Epoxy-ketone

The reaction of 2,2-dimethyl-5-(1,2-epoxypropyl)cyclohexanone (7) with t-BuOK, in DMSO furnished a small amount of 5-(1-hydroxyprop-2-enyl)-2,2-dimethylcyclohexanone (12) and the 4 unexpected products 13-16 which contain one to three additional C-atoms (Scheme 2).The relative configuration of the major product 1-(4',4'-dimethyl-2',3'-dimethylidenecyclohexyl)propane-1,2-diol (15) was shown to be 1RS,2RS, 1'SR via NOE measurements performed on a derivative thereof.A crossover experiment in DMSO/DMSO 1:1 as solvent showed that the two additional C-atoms of this product originate from a single molecule of DMSO (Scheme 5).A tentative mechanistic scheme, consistent with all experimental observations, is proposed which involves a -sigmatropic corroborated part of this hypothetic scheme by taking recourse to a model compound (7-(methylsulfinyl)-p-mentha-1,8-diene (32/33), readily prepared in two steps from perilla alcohol (39)), which reacted as predicted by the proposed mechanism (Schemes 9 and 10).