797055-37-9

Basic information

• Product Name: Spiro[4.5]dec-6-ene-2-carboxylic acid, 6,10-dimethyl-, methyl ester, (5R,10R)-rel- (9CI)
• Synonyms: Spiro[4.5]dec-6-ene-2-carboxylic acid, 6,10-dimethyl-, methyl ester, (5R,10R)-rel- (9CI)
• CAS NO: 797055-37-9
• Molecular Formula: C14H22O2
• Molecular Weight: 222.32328
• Product Categories: METHYL
• Mol File: 797055-37-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Spiro[4.5]dec-6-ene-2-carboxylic acid, 6,10-dimethyl-, methyl ester, (5R,10R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[4.5]dec-6-ene-2-carboxylic acid, 6,10-dimethyl-, methyl ester, (5R,10R)-rel- (9CI)(797055-37-9)
• EPA Substance Registry System: Spiro[4.5]dec-6-ene-2-carboxylic acid, 6,10-dimethyl-, methyl ester, (5R,10R)-rel- (9CI)(797055-37-9)

Safety Data

• Hazardous Substances Data: 797055-37-9(Hazardous Substances Data)

Upstream product

• 121741-13-7 6-Hydroxy-6,10-dimethyl-spiro[4.5]decane-2-carboxylic acid methyl ester 
• 79265-78-4 (2S^*,5S^*,10R^*)-2-hydroxy-6,10-dimethylspiro<4.5>dec-6-en-8-one 
• 120-92-3 cyclopentanone 
• 155528-07-7 (+)-(3R,4E)-3-(tert-butyldimethylsilyloxy)hex-4-enal 
• 928203-31-0 6-(tert-butyl-dimethyl-silanyloxy)-10-methyl-spiro[4.5]dec-1-ene-2-carboxylic acid methyl ester 
• 928203-27-4 6-(tert-butyl-dimethyl-silanyloxy)-10-methyl-spiro[4.5]decan-1-one 
• 928203-22-9 2-[3-(tert-butyl-dimethyl-silanyloxy)-hex-4-enoyl]-cyclopentanone 
• 928203-21-8 2-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-hex-4-enyl]-cyclopentanone 
• 928203-26-3 10-(tert-butyl-dimethyl-silanyloxy)-6-methyl-spiro[4.5]dec-7-en-1-one 
• 928203-25-2 tert-butyl-dimethyl-(2-propenyl-2,3,4,5,6,7-hexahydro-cyclopenta[b]pyran-4-yloxy)-silane 
• 928203-32-1 6-hydroxy-10-methyl-spiro[4.5]dec-1-ene-2-carboxylic acid methyl ester 
• 58150-20-2 6-methyl-10-oxo-spiro[4.5]decane-2-carboxylic acid methyl ester 
• 928203-28-5 6-methyl-10-oxo-spiro[4.5]dec-1-ene-2-carboxylic acid methyl ester 
• 928203-23-0 2-(3-hydroxy-hex-4-enoyl)-cyclopentanone 

Relevant articles and documents

Claisen rearrangement strategy in alkenyl dihydropyran leading to total synthesis of (+)-α-vetispirene and (-)-agarospirol

Total synthesis of (+)-α-vetispirene and (-)-agarospirol based on a Claisen rearrangement has been achieved. This is the first example of a Claisen rearrangement in an enantio-enriched alkenyl bicyclic dihydropyran system with perfect asymmetric transmission. Copyright

Stereoselective total synthesis of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone based on a Claisen rearrangement

The stereoselective total syntheses of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone were accomplished based on a Claisen rearrangement in an alkenyl bicyclic dihydropyran system. The most striking feature of this approach is that the Claisen rearrangement of bicyclic dihydropyran proceeds stereoselectively to provide a multi-functionalized spiro[4.5]decane, which is an efficient precursor for the synthesis of the vetivane sesquiterpenes.

Connective synthesis of spirovetivanes: Total synthesis of (±)-agarospirol, (±)-hinesol and (±)-α-vetispirene

A concise, connective synthesis of naturally occurring spirovetivanes 1 and 3, in racemic form, is presented. This novel approach involves the efficient assembly of the advanced intermediate 12 through a unique spiroannulation protocol. Wiley-VCH Verlag GmbH & Co. KGaA1 69451 Weinheim, Germany, 2004.

A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol

In one step, the skeleton of cis-spirovetivanes was constructed with high stereoselectivity by the phosphine-catalyzed [3+2] cycloaddition reaction of tert-butyl 2,3-butadienoate or 2-butynoate with 3-methyl-2-methylenecyclohexanone (5). This method was exemplified by the first highly efficient total synthesis of natural product (-)-hinesol, which is an active ingredient of cerebral circulation and metabolism improvers.

Synthesis based on cyclohexadienes. Part 21. Total synthesis of (±)-hinesol and (±)-10-epi-hinesol

An efficient strategy for the construction of the spiro[4.5]decane and eremane systems is described which involves an acid-catalysed rearrangement of an endo alcohol, followed by an oxidative cleavage resulting in the generation of a spiro-system, as the key step. This methodology is extended to the total synthesis of (±)-hinesol and (±)-10-epi-hinesol 2.

A NOVEL SKELETAL REARRANGEMENT OF BICYCLO(2.2.2)OCTENES THROUGH BICYCLO(3.2.1)OCTENE SYSTEM: SYNTHESIS OF (+/-)-HINESOL AND (+/-)-10-epi-HINESOL

Acid catalysed rearrangement of the endo-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties.An efficient entry into spiro(4,5)decane and eremane system, as exemplified by the total synthesis of (+/-)-hinesol (2) and its 10-epimer (3) is reported.

A New Synthesis of (+/-)-Agarospirol and (+/-)-Hinesol

(+/-)-Agarospirol (8) and (+/-)-hinesol (9) were simultaneously synthesized via a useful synthon in the synthesis of spirovetivane-type sesquiterpenes, i.e., (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one (1), which had previously been prepared from the corresponding phenolic α-diazoketone via the spiro-annelation reaction and subsequent stereo-controlled Birch reduction, both reported in our previous communications.Keywords-(+/-)-agarospirol; (+/-)-hinesol; spirovetivane-type sesquiterpenes; useful synthon; (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one