89949-50-8

Basic information

• Product Name: 2-((1S,4R)-4,8-Dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol
• CAS NO: 89949-50-8
• Molecular Weight: 224.387
• Mol File: 89949-50-8.mol

Chemical Properties

• CAS DataBase Reference: 2-((1S,4R)-4,8-Dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((1S,4R)-4,8-Dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol(89949-50-8)
• EPA Substance Registry System: 2-((1S,4R)-4,8-Dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol(89949-50-8)

Safety Data

• Hazardous Substances Data: 89949-50-8(Hazardous Substances Data)

Upstream product

• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 65408-94-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>deca-6,8-diene 

Relevant articles and documents

Novel Cyclopentabenzofuran Intermediates for the Synthesis of Acorane-Alaskane Sesquiterpenes: Total Synthesis of (+/-)-β-Acorenol and (+/-)-Acorenone

Cyclopentabenzofuran derivatives (5a) and (5b) were synthesized from spirodienone esters (6a) and (6b), respectively, and the utility of these intermediates in acorane-alaskane sesquiterpene synthesis is illustrated by their conversion into (+/-)-β-acorenol (4a) and (+/-)-acorenone (1).

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. Total Synthesis of (+/-)-Acorenone

The metal-ammonia reduction of the cyclopentabenzofuran derivative (2b) afforded a mixture of 4-epi-β-acorenol (5), a disubstituted olefin (8) as the main product, and a perhydro compound (9).Compound 8 was converted to 5 via the exo-diene (15).Dehydration of 5 afforded the 4-epi-β-acoradiene (6), selective reduction of which gave the monoolefin (7), and then the allylic oxidation of 7 gave (+/-)-acorenone (3) in good yield.Keywords - acorane-alaskane sesquiterpene; acorenone; cyclopentabenzofuran; total synthesis; 4-epi-β-acorenol; 4-epi-α-acorenol; 4-epi-β-acoradiene; metal-ammonia reduction; conjugate reduction; terminal olefin reduction.