198405-00-4

Basic information

• Product Name: Cyclopropanemethanol, 1-methyl-2-[[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl]-
• CAS NO: 198405-00-4
• Molecular Formula: C15H26O
• Mol File: 198405-00-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclopropanemethanol, 1-methyl-2-[[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanemethanol, 1-methyl-2-[[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl]-(198405-00-4)
• EPA Substance Registry System: Cyclopropanemethanol, 1-methyl-2-[[(1S,3R,5R)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl]methyl]-(198405-00-4)

Safety Data

• Hazardous Substances Data: 198405-00-4(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 210115-64-3 (E)-2-methyl-4-((1S,3S,5R)-1,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)but-2-en-1-ol 
• 74-95-3 1,1-dibromomethane 
• 198405-38-8 (E)-(R)-2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-ol 
• 1067637-16-4 (trans)-(1-methyl-2-(((R)-2,2,3-trimethylcyclopent-3-enyl)methyl)cyclopropyl)-methanol 

Relevant articles and documents

Cyclopropanation with dibromomethane under grignard and barbier conditions

Tertiary Grignard reagents and dibromomethane efficiently cyclopropanate allylic (and certain homoallylic) magnesium and lithium alcoholates at ambient temperature in ether solvents. Lithium (homo)allyl alcoholates are directly cyclopropanated with magnes

Tandem cyclopropanation with dibromomethane under Grignard conditions

(Chemical Equation Presented) Tertiary Grignard reagents and dibromomethane efficiently cyclopropanate allylic (and certain homoallylic) magnesium and lithium alcoholates at ambient temperature in ether solvents. Lithium (homo)allyl alcoholates are directly cyclopropanated with magnesium and CH 2Br2 under Barbier conditions at higher temperatures. The reaction rates depend on the substitution pattern of the (homo)allylic alcoholates and on the counterion with lithium giving best results. Good to excellent syn-selectivities are obtained from α-substituted substrates, which are in accord with a staggered Houk model. In tandem reactions, cyclopropyl carbinols are obtained from allyloxylithium or -magnesium intermediates, generated in situ by alkylation of conjugated aldehydes, ketones, and esters as well as from allyl carboxylates or vinyloxiranes. Using this methodology, numerous fragrance ingredients and their precursors were efficiently converted to the corresponding cyclopropyl carbinols.