144342-39-2

Basic information

• Product Name: (+)-(1R,3S)-6,6-Dimethylspiroheptane-2,1'-cyclopropan>-3-yl acetate
• CAS NO: 144342-39-2
• Molecular Weight: 208.301
• Mol File: 144342-39-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-(1R,3S)-6,6-Dimethylspiroheptane-2,1'-cyclopropan>-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R,3S)-6,6-Dimethylspiroheptane-2,1'-cyclopropan>-3-yl acetate(144342-39-2)
• EPA Substance Registry System: (+)-(1R,3S)-6,6-Dimethylspiroheptane-2,1'-cyclopropan>-3-yl acetate(144342-39-2)

Safety Data

• Hazardous Substances Data: 144342-39-2(Hazardous Substances Data)

Upstream product

• 64-19-7 acetic acid 
• 140632-14-0 nopylamine 
• 144342-18-7 (-)-(1R)-2-(2-Iodoethyl)-6,6-dimethylbicyclo<3.1.1>hept-2-ene 

Relevant articles and documents

3α-Acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′- cyclopropane from nopylamine deamination

Deamination of nopylamine hydrochloride with sodium nitrite in acetic acid yields nopyl chloride 8, nopyl acetate 1 (R = OAc), 2-(1-acetoxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene 9 and 3α-acetoxy-6,6-dimethylbicyclo[3.1.1]heptane-2-spiro-1′-cyclopropane 12. The products are consistent with initial formation of a diazonium ion which reacts by nucleophilic attack, hydride shift or by shift of electrons of the double bond. The reaction is contrasted with the acetolysis of nopyl toluene-p-sulfonate, which yields 8,8-dimethyltricyclo[4.2.1.03,7]nonan-6-ol as the main product. The difference is suggested to result from the transition state being reached early (deamination) or late (toluene-p-sulfonate acetolysis) on the reaction coordinate.