28296-85-7

Basic information

• Product Name: Spiro[4.5]dec-7-ene-1-methanol,a,a,4,8-tetramethyl-, (1R,4R,5S)-
• Synonyms: Spiro[4.5]dec-7-ene-1-methanol,a,a,4,8-tetramethyl-, (1R,4R,5S)-(-)- (8CI);Spiro[4.5]dec-7-ene-1-methanol, a,a,4,8-tetramethyl-, [1R-(1a,4b,5a)]-; (-)-a-Acorenol;Acorenol; a-Acorenol
• CAS NO: 28296-85-7
• Molecular Formula: C15H26 O
• Molecular Weight: 222.371
• Mol File: 28296-85-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 312.2±11.0 °C(Predicted)
• Density: 0.96±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Spiro[4.5]dec-7-ene-1-methanol,a,a,4,8-tetramethyl-, (1R,4R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[4.5]dec-7-ene-1-methanol,a,a,4,8-tetramethyl-, (1R,4R,5S)-(28296-85-7)
• EPA Substance Registry System: Spiro[4.5]dec-7-ene-1-methanol,a,a,4,8-tetramethyl-, (1R,4R,5S)-(28296-85-7)

Safety Data

• Hazardous Substances Data: 28296-85-7(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 955007-44-0 C₁₅H₂₂O₃ 
• 955007-45-1 C₁₃H₁₈O₃ 
• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 43219-78-9 2-Cyclohex-1-enyl-hex-5-enoic acid ethyl ester 
• 4709-59-5 ethyl 2-(1-cyclohexenyl)acetate 
• 74320-28-8 (1R^*,3aR^*,5aR^*,9aR^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 917-54-4 methyllithium 
• 74320-29-9 rac-(1R,3aS,5aS,9aR)2,3,3a,4,6,9-hexahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 132557-04-1 (1R,4S,5S)-4,8-Dimethyl-spiro[4.5]dec-7-ene-1-carboxylic acid 2-hydroxy-ethyl ester 
• 121322-15-4 2-((1S,4R,5S)-6,7-Dibromo-4,8-dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol 
• 89949-49-5 2-((1S,4R,5R)-4,8-Dimethyl-spiro[4.5]dec-6-en-1-yl)-propan-2-ol 

Downstream Products

• 28400-12-6 β-alaskene 
• 24048-44-0 (+/-)-β-acoradiene 
• 5956-05-8 (+/-)-acorenone 
• 24048-44-0 (+/-)-4-epi-β-acoradiene 
• 24048-44-0 α-alaskene 
• 5956-05-8 (+/-)-acorenone B 
• 5956-05-8 4-epi-acorenone 

Relevant articles and documents

Total syntheses of (±)-α-acorenol, β-acorenol, α-epi-acorenol and β-epi-acorenol via an Ireland ester Claisen rearrangement and RCM reaction sequence

Total syntheses of (±)-α- and β-acorenols and (±)-α- and β-epi-acorenols, spiro[4.5]decane sesquiterpenes, isolated from the western Australian sandalwood oil, have been accomplished employing a combination of Ireland ester Claisen rearrangement and RCM r

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.

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).