110990-41-5

Basic information

• Product Name: (6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene
• Synonyms: (1R)-7-Isopropyl-4-methylene-1α,9aα-dimethyl-1,2,3,3aα,4,5,6,8,9,9a,10,10aβ-dodecahydrodicyclopenta[a,d]cyclooctene;(6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene;Cycloaraneosene
• CAS NO: 110990-41-5
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.46808
• Mol File: 110990-41-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene(CAS DataBase Reference)
• NIST Chemistry Reference: (6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene(110990-41-5)
• EPA Substance Registry System: (6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene(110990-41-5)

Safety Data

• Hazardous Substances Data: 110990-41-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
Dicyclopentadiene is used as a chemical intermediate for the production of dicyclopentadiene resins, which are utilized in the manufacturing of coatings, adhesives, and sealants. These resins provide excellent adhesion, chemical resistance, and flexibility, making them suitable for various applications in the chemical industry.
Used in Pesticide Production:
Dicyclopentadiene is also used in the production of pesticides. Its unique chemical properties make it a valuable component in the synthesis of various pesticide formulations, contributing to their effectiveness in controlling pests and protecting crops.
Used in Polymer Synthesis:
As a monomer, dicyclopentadiene is used in the synthesis of cyclic olefin copolymers. These copolymers exhibit excellent heat resistance, transparency, and mechanical properties, making them suitable for use in various high-performance applications, such as optical media and electrical insulation.
Used in Paints and Varnishes:
Dicyclopentadiene can be found in consumer products like paints and varnishes. Its strong odor and chemical properties contribute to the drying process and overall performance of these coatings, providing durability and resistance to various environmental factors.
Used as a Reactive Diluent in Epoxy Resins:
In the epoxy resin industry, dicyclopentadiene is used as a reactive diluent. It helps to reduce the viscosity of epoxy resins, making them easier to process and apply. This property is particularly useful in the manufacturing of composite materials and coatings, where lower viscosity resins can improve the flow and curing characteristics.
Used in Rubber and Plastics Manufacturing:
Dicyclopentadiene is also a component in the production of rubber and plastics. Its unique chemical structure allows it to be incorporated into various formulations, enhancing the properties of the final products, such as flexibility, durability, and resistance to chemicals and heat.

Upstream product

• 110990-42-6 9α-hydroxycycloaraneosene 
• 122053-34-3 (R)-2-[(S)-2-((1S,2S,3S)-2-Hydroxymethyl-3-isopropyl-1-methyl-cyclopentylmethyl)-3-methyl-cyclopent-2-enyl]-propan-1-ol 
• 110990-54-0 (1S,2S,5S)-5-Isopropyl-2-methyl-2-[(1R,2R,5R)-2-methyl-5-((R)-1-methyl-2-oxo-ethyl)-cyclopentylmethyl]-cyclopentanecarbaldehyde 
• 110990-57-3 (S)-5-[(1R,2R,5R)-2-(1-Hydroxymethyl-vinyl)-5-methyl-cyclopentylmethyl]-2-isopropyl-5-methyl-cyclopent-1-enecarbaldehyde 
• 107493-57-2 [(R)-[(1R,3S)-3-((R)-2-Benzyloxy-1-methyl-ethyl)-1-methyl-2-methylene-cyclopentyl]-((S)-5-isopropyl-2-methyl-cyclopent-1-enyl)-methoxy]-trimethyl-silane 
• 122053-35-4 {(1S,2S,5S)-2-[(S)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopentyl}-methanol 
• 93178-07-5 (R)-[(1R,3S)-3-((R)-2-Benzyloxy-1-methyl-ethyl)-1-methyl-2-methylene-cyclopentyl]-((S)-5-isopropyl-2-methyl-cyclopent-1-enyl)-methanol 
• 110990-53-9 (R)-2-[(1R,2R,3R)-2-((1S,2S,3S)-2-Hydroxymethyl-3-isopropyl-1-methyl-cyclopentylmethyl)-3-methyl-cyclopentyl]-propan-1-ol 
• 110990-55-1 (1S,3S)-3-Isopropyl-1-methyl-1-[(1R,2R,5R)-2-methyl-5-((E)-1-methyl-2-trimethylsilanyloxy-vinyl)-cyclopentylmethyl]-2-[1-trimethylsilanyloxy-meth-(E)-ylidene]-cyclopentane 
• 110990-51-7 Acetic acid (1S,2S,5S)-2-[(S)-5-((R)-2-acetoxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopentylmethyl ester 
• 110990-52-8 (R)-2-{(S)-2-[(1S,2S,3S)-3-Isopropyl-1-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopentylmethyl]-3-methyl-cyclopent-2-enyl}-propan-1-ol 
• 111023-97-3 2-((1R,2R,3R)-2-{(1S,3S)-3-Isopropyl-1-methyl-2-[1-trimethylsilanyloxy-meth-(E)-ylidene]-cyclopentylmethyl}-3-methyl-cyclopentyl)-propenal 
• 62994-35-8 (5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde 
• 110990-43-7 Acetic acid (4S,6aR,9R,9aR,10aS)-3-isopropyl-9,10a-dimethyl-6-methylene-1,2,4,5,6,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-4-yl ester 

Relevant articles and documents

A Total Synthesis of 8β-Hydroxycycloaraneosene by Means of an Eight-Membered Ring-Formation via a Lewis Acid-Catalyzed Ene Reaction. Confirmation of Its Natural Occurrence

An improved eight-membered ring closure by means of a Lewis-acid-catalyzed ene reaction was applied to the synthesis of cycloaraneosene and its congener, "hydroxycycloaraneosene".Comparisons of the NMR spectral data of the synthetic and natural compounds established that the natural product possesses an 8β-hydroxy structure, not the originally proposed 9α-hydroxy one.

Structure Elucidation of "Hydroxycycloaraneosene" by Unambiguous Total synthesis. An Eight-Membered Ring Formation via a Lewis Acid-Catalyzed Ene-Reaction

An improved eight-membered ring closure by means of a Lewis acid-catalyzed ene-reaction of an iridoid dimer produced a tricyclic derivative wich was further converted to cycloaraneosene and its congener, "hydroxycycloaraneosene".Total synthesis of the latter established its structure to be 8β-hydroxy derivative, not as the originally-proposed 9α-.

Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of "epi"-Fusicoccane Diterpenoids, and the Structure Revision of Its Congener, Hydroxycycloaraneosene

The 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via the stereoselective condensation of two units of optically active iridoids, Cope rearrangement and chemical reduction of the tetrasubstituted C=C bond.The NMR spectrum of synthetic 9α-hydroxycycloaraneosene was not identical with the congener product, and the natural alcohol is likely to be 8β-hydroxyl derivative.

Synthetic Photochemistry. XLII. Total Synthesis of Cycloaraneosene, a Fundamental Hydrocarbon of 5-8-5-Membered Tricyclic Diterpenoid from Sordaria araneosa

A 5-8-5-membered tricyclic diterpene, cycloaraneosene, has been totally synthesized via a stereoselective condensation of two units of optically active iridoids, a Cope rearrangement, a chemical reduction of the tetrasubstituted double bond, and the formation of an eight-membered ring.The proposed structure of natural hydroxycycloaraneosene should be revised to 8β-hydroxycycloaraneosene, judging from the NMR spectral data.