1136-29-4

Basic information

• Product Name: [4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene
• CAS NO: 1136-29-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 1136-29-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: [4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene(1136-29-4)
• EPA Substance Registry System: [4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene(1136-29-4)

Safety Data

• Hazardous Substances Data: 1136-29-4(Hazardous Substances Data)

Usage

General Description

"[4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene" is a chemical compound with the molecular formula C15H24. It is a polycyclic hydrocarbon that consists of a bicyclic structure with a fused cyclohexane and cyclopentane ring. [4S,4aβ,8aβ,(+)]-Decahydro-1,6-bis(methylene)-4-isopropylnaphthalene is also known as (+)-1,6-Diisopropylnaphthalene and is used in the synthesis of pharmaceuticals, fragrance, and flavoring agents. It has a musky, floral, and slightly woody odor and is used in perfumery as a fragrance ingredient. Additionally, it is used in the production of rubber and in the manufacture of lubricants and other industrial products. This chemical compound is usually handled under standard laboratory practices and protective measures due to its potential hazards and should be stored away from sources of ignition and incompatible materials.

Upstream product

• 481-35-6 4,10-dichloro-1β,4ξH,10ξH-cadinane 
• 24268-39-1 γ-muurolene 
• 483-75-0 (-)-α-muurolene 
• 106777-60-0 (1R*,5S*,6R*,8S*)-(+/-)-8-Hydroxy-5-isopropylbicyclo<4.4.0>decan-2-on 
• 106777-60-0 (1R*,5S*,6R*,8R*)-(+/-)-8-Hydroxy-5-isopropylbicyclo<4.4.0>decan-2-on 
• 106777-64-4 (1R*,5S*,6R*,8S*)-(+/-)-5-Isopropyl-2-methylenbicyclo<4.4.0>decan-8-ol 
• 106777-59-7 2,8-Diacetoxy-5-isopropylbicyclo<4.4.0>dec-1-en 
• 106777-57-5 N,N-Diethyl<6-(3-butenyl)-4-isopropyl-1,4-cyclohexadienyl>oxyethylamin 
• 106777-58-6 2-(3-Butenyl)-4-isopropyl-2-cyclohexen-1-on 
• 80873-83-2 1-(2-Diethylaminoethoxy)-4-isopropyl-cyclohexadien-1,4 
• 105453-16-5 germacrene D 
• 1080-68-8 (1R*,5S*,6R*)-(+/-)-5-Isopropylbicyclo<4.4.0>decan-2,8-dion 
• 19493-09-5 Methylenetriphenylphosphorane 
• 27548-51-2 (1R*,5S*,6R*)-(+/-)-5-Isopropyl-2-methylenbicyclo<4.4.0>decan-8-on 

Downstream Products

• 1080-67-7 (+)-ε-Cadinen 
• 16641-30-8 4,10-dichloro-4βH,10βH-cadinane 
• 481-35-6 4,10-dichloro-1β,4ξH,10ξH-cadinane 
• 483-73-8 cis-cadinane 

Relevant articles and documents

The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements

Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane, and bourbonane group as well as isogermacrene D were identified as main products and made available as reference compounds for structure investigations and stereochemical assignments of plant constituents. δ-Amorphene, one of the rearrangement products, was identified as a natural product for the first time. The absolute configuration of γ-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. (C) 2000 Elsevier Science Ltd.

Lewis Acid Assisted Annelation of Trimethylsilyl Enol Ethers of 1-Acetylcyclohexenes with α,β-Unsaturated Carbonyl Compounds to give Substituted 2-Decalones; Synthesis of (+/-)-ε-Cadinene

The trimethylsilyl enol ethers of 1-acetylcyclohexenes undergo a Lewis-acid-assisted one-pot annelation reaction with α,β-unsaturated carbonyl compounds to produce 5-substituted 2-decalones; the application of this reaction has enabled a synthesis of (+/-)-ε-cadinene (12).

CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS

Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.