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
• Article Data: 4

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

General Description

(6aR)-3-Isopropyl-1,2,4,5,6,6aβ,7,8,9,9aα,10,10a-dodecahydro-6-methylene-9β,10aβ-dimethyldicyclopenta[a,d]cyclooctene, also known as dicyclopentadiene, is a stable, colorless liquid with a strong odor. It is primarily used as a chemical intermediate in the production of dicyclopentadiene resins, which are used in the manufacturing of coatings, adhesives, and sealants. Additionally, it is utilized in the production of pesticides and as a monomer in the synthesis of cyclic olefin copolymers. Dicyclopentadiene can also be found in consumer products such as paints and varnishes. Furthermore, it is used as a reactive diluent in epoxy resins and as a component in rubber and plastics manufacturing.

Upstream product

• 123298-66-8 {(E)-2-[(1R,2R,3R)-2-((1S,3S)-3-Isopropyl-1-methyl-2-methylene-cyclopentylmethyl)-3-methyl-cyclopentyl]-propenyloxy}-trimethyl-silane 
• 123298-64-6 (R)-2-[(1R,2R,3R)-2-((1S,3S)-3-Isopropyl-1-methyl-2-methylene-cyclopentylmethyl)-3-methyl-cyclopentyl]-propan-1-ol 
• 123298-62-4 2,2-Dimethyl-propionic acid (R)-2-{(1R,2R,3R)-2-[(1S,2S,3S)-3-isopropyl-1-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopentylmethyl]-3-methyl-cyclopentyl}-propyl ester 
• 123313-62-2 2,2-Dimethyl-propionic acid (R)-2-[(1R,2R,3R)-2-((1S,2S,3S)-2-hydroxymethyl-3-isopropyl-1-methyl-cyclopentylmethyl)-3-methyl-cyclopentyl]-propyl ester 
• 123313-63-3 2,2-Dimethyl-propionic acid (R)-2-[(1R,2R,3R)-2-((1S,3S)-3-isopropyl-1-methyl-2-methylene-cyclopentylmethyl)-3-methyl-cyclopentyl]-propyl ester 
• 122039-02-5 8,9-seco-(2R,3R,6R,7R,10S,11S,14S)-8-Hydroxy-9-(2-tetrahydropyranyloxy)-cycloaraneosane 
• 123298-65-7 (R)-2-[(1R,2R,3R)-2-((1S,3S)-3-Isopropyl-1-methyl-2-methylene-cyclopentylmethyl)-3-methyl-cyclopentyl]-propionaldehyde 
• 123298-56-6 2-[(1R,2R,3R)-2-((1S,3S)-3-Isopropyl-1-methyl-2-methylene-cyclopentylmethyl)-3-methyl-cyclopentyl]-propenal 
• 122089-79-6 (1S,2S,5S)-2-[(S)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopentanecarbaldehyde 
• 122089-80-9 (1R,2S,5S)-2-[(S)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopentanecarbaldehyde 
• 122038-93-1 2-{(1S,2S,5S)-2-[(S)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopentylmethoxy}-tetrahydro-pyran 
• 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 
• 107398-22-1 [(2S,5S)-2-[(S)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-2-methyl-cyclopent-1-enylmethyl]-5-isopropyl-2-methyl-cyclopent-(E)-ylidenemethoxy]-trimethyl-silane 
• 122038-99-7 Methanesulfonic acid 2-[(1R,2R,3R)-2-((S)-2-formyl-3-isopropyl-1-methyl-cyclopent-2-enylmethyl)-3-methyl-cyclopentyl]-allyl 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.

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.