122437-21-2

Basic information

• Product Name: (3R*,3aR*,5aR*,8aR*)-3,3a,5,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopentapentalene
• CAS NO: 122437-21-2
• Molecular Weight: 204.356
• Mol File: 122437-21-2.mol

Chemical Properties

• CAS DataBase Reference: (3R*,3aR*,5aR*,8aR*)-3,3a,5,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopentapentalene(CAS DataBase Reference)
• NIST Chemistry Reference: (3R*,3aR*,5aR*,8aR*)-3,3a,5,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopentapentalene(122437-21-2)
• EPA Substance Registry System: (3R*,3aR*,5aR*,8aR*)-3,3a,5,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopentapentalene(122437-21-2)

Safety Data

• Hazardous Substances Data: 122437-21-2(Hazardous Substances Data)

Upstream product

• 122437-20-1 (5R*,6S*,7S*)-6,7,11,11-tetramethyldispiro<3.0.4.2>undecan-6-ol 

Relevant articles and documents

Synthesis of tricyclopentanoid sesquiterpenes via rearrangement routes: (±)-modhephene, (±)-epimodhephene and (±)-isocomene

Based on model studies with dispiroundecane 10, dispiroundecane 1 has been synthesized and rearranged to (±)-modhephene 6 and (±)-isocomene 7. The epimeric dispiroundecane 9 yields (±)-epimodhephene 12. A total of thirteen rearrangement products (6, 7, 12, 37, 38, 39, 42, 44, 55, 57, 64, 67) have been isolated from 1 and/or 9, including six unnatural triquinanes. Two of these (55, 57) are formed by unusual 1,3- and 1,4-shifts, respectively. A mechanistic rationale on the basis of force field calculations is given.

(+/-)MODHEPHENE AND (+/-)ISOCOMENE VIA CASCADE REARRANGEMENT

Dispiroundecane 1 has been synthesized and rearranged to (+/-)modhephene 2 and triquinane 3 under kinetic control, and to (+/-)isocomene 4 and triquinane 5 under thermodynamic control.Molecular mechanics calculations (MM2) support the mechanism proposed.