24286-51-9

Basic information

• Product Name: Casbene
• Synonyms: (-)-casbene;Casbene
• CAS NO: 24286-51-9
• Molecular Formula: C20H32
• Molecular Weight: 272.46808
• Mol File: 24286-51-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 357.7°C at 760 mmHg
• Flash Point: 162°C
• Appearance: /
• Density: 0.853g/cm³
• Vapor Pressure: 5.5E-05mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: Casbene(CAS DataBase Reference)
• NIST Chemistry Reference: Casbene(24286-51-9)
• EPA Substance Registry System: Casbene(24286-51-9)

Safety Data

• Hazardous Substances Data: 24286-51-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H32/c1-15-8-6-10-16(2)12-13-18-19(20(18,4)5)14-17(3)11-7-9-15/h9-10,14,18-19H,6-8,11-13H2,1-5H3/b15-9-,16-10+,17-14+/t18-,19+/m0/s1

Upstream product

• 68254-38-6 (2E,6E,10E)-1-diazo-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraene 
• 13920-11-1 2E,6E,10E-geranylgeranyl aldehyde 
• 1067-74-9 Methyl diethylphosphonoacetate 
• 5460-63-9 (+/-)-cis-Chrysanthemsaeure-methylester 
• 59372-97-3 (-)-cis-1,1-dimethyl-2-(4-methoxycarbonyl-3-methylbut-3-enyl)-3-(6-methoxycarbonyl-2-methylhepta-1,5-dienyl)cyclopropane 
• 59372-98-4 (2E,6E)-7-[(1R,3S)-3-((E)-5-Hydroxy-3-methyl-pent-3-enyl)-2,2-dimethyl-cyclopropyl]-2,6-dimethyl-hepta-2,6-dien-1-ol 
• 59372-99-5 (2R,3S)-2-((1Z,5E)-7-Bromo-2,6-dimethyl-hepta-1,5-dienyl)-3-((E)-5-bromo-3-methyl-pent-3-enyl)-1,1-dimethyl-cyclopropane 
• 110589-91-8 (+)-cis-2,2-dimethyl-3-<3,7-dimethyl-11-oxo-3(E),7(E)-dodecadienyl>cyclopropanecarbaldehyde 

Relevant articles and documents

Concise synthesis of cembrenes based on radical-mediated vinylcyclopropane ring-opening reactions in casbene

Treatment of the bicyclopentadecatriene casbene 1 with ethanethiol radical (EtSH in C6H6, heat) results in regiospecific 1,4-addition to the vinylcyclopropane ring system, producing the cembrene sulfide 10.In similar reactions chrysanthemyl alcohol 11 and carene 13 lead exclusively to the corresponding sulfides 12 and 14, respectively, whereas irradiation of methyl chrysanthemate 15 with ethanethiol produces a 1:1 mixture of the isomeric sulfides 16 and 17.Oxidation of the cembrene sulfide 10, followed by thermolysis of the resulting sulfoxide then produces isocembrene 20, identical with natural material from Pinus sibirica.When a solution of casbene 1 in CCl4 was heated in the presence of NBS and AIBN, it underwent smooth oxidative rearrangement, via 21 and 22, to cembrenene 23, identical with the natural product isolated from the soft coral Sinularia maji.

Synthesis of Macrocyclic Terpenoid Hydrocarbons by Intramolecular Carbonyl Coupling: Bicyclogermacrene, Lepidozene, and Casbene

Total syntheses of two germacrane sesquiterpenes, bicyclogermacrene (1) and lepidozene (2), and of the cembrane sesquiterpene casbene (3) are discussed.Bicyclogermacrene and lepidozene were prepared in seven steps from geranylacetone by routes that involve titanium-induced cyclizations of cis- and trans-2,2-dimethyl-3-cyclopropanecarbaldehyde, respectively. (+)-Casbene was prepared from (+)-2-carene and 6-methyl-5-hepten-2-one by a route whose key steps were the palladium-catalysed cross-coupling of vinylic iodide 31 with homoallylic organozinc reagent 32 and titanium-induced cyclization of cis-2,2-dimethyl-3-cyclopropanecarbaldehyde (16).

Total Synthesis of the Macrocyclic Diterpene (-)-Casbene, The Putative Biogenetic Precursor of Lathyrane, Tigliane, Ingenane, and Related Terpenoid Structures

A total synthesis of the bicyclic diterpene 1S,3R(-)-casbene (19), based on elaboration of 1R,3S(+)-cis-chrystanthemic acid (21) to the bis-allylic bromide (20), followed by closure of the 14-membered ring with tetracarbonylnickel, is described.Sy