Berkheyaradulene

Base Information

• Chemical Name: Berkheyaradulene
• CAS No.: 65372-78-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Mol file: 65372-78-3.mol

Synonyms:Cyclopenta[c]pentalene,1,2,3,3a,5a,6,7,8-octahydro-1,3a,4,5a-tetramethyl-, [1R-(1a,3aa,5ab,8aR*)]-; (-)-Isocomene; (-)-a-Isocomene; Berkheyaradulene; Isocomene; a-Isocomene

Chemical Property of Berkheyaradulene

Chemical Property:

• Boiling Point: 254.9±7.0 °C(Predicted)
• Density: 0.95±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Berkheyaradulene

There total 47 articles about Berkheyaradulene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

decahydro-1,3a,5a-trimethyl-4-methylene-cyclopenta[c]pentalene (71596-72-0,74311-15-2,75171-54-9,78961-84-9,82467-49-0,84984-78-1,92619-56-2) → isocomene (65372-78-3,71629-00-0,82467-48-9,84984-77-0,92619-57-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(01)81201-6

Reference yield: 92.0%

β-epiisocomene (71596-72-0,74311-15-2,75171-54-9,78961-84-9,82467-49-0,84984-78-1,92619-56-2) → Epiisocomene (65372-78-3,71629-00-0,82467-48-9,84984-77-0,92619-57-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(01)81201-6

Reference yield:

(3aR,4R,7S,7aR)-2-Hydroxymethyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one (325142-36-7) → isocomene (65372-78-3,71629-00-0,82467-48-9,84984-77-0,92619-57-3)

Guidance literature:

Multi-step reaction with 22 steps

1: DIBAL

2: 99 percent / NBS / CH₂Cl₂ / 0 °C

3: 87 percent / diphenyl ether / Heating

4: 75 percent / LDA / tetrahydrofuran / -78 °C

5: 66 percent / DMSO / CH₂Cl₂ / Heating

6: 94 percent / tetrahydrofuran / -20 °C

7: p-TsOH

8: 90 percent / Li(Et)3BH / tetrahydrofuran

9: 87 percent / NaH / tetrahydrofuran

10: 85 percent / Zn; acetic acid / ethanol / Heating

11: 91 percent / NaHCO₃ / diphenyl ether / Heating

12: 93 percent / NH₂NH₂*H₂O; K₂CO₃; TEG / 250 °C

13: Ph₃P; DIAD / CH₂Cl₂ / 20 °C

14: aq. NaOH / methanol / 20 °C

15: 81 percent / MnO₂ / CH₂Cl₂ / 20 °C

16: 67 percent / t-BuOK; HMPA / tetrahydrofuran / -25 °C

17: 89 percent / CuBr-Me₂S

18: H₂ / 10percent Pd/C

19: Bu₃P

20: m-CPBA / -78 °C

21: CaCO₃ / diphenyl ether / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; tributylphosphine; di-isopropyl azodicarboxylate; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; calcium carbonate; zinc; lithium diisopropyl amide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; 10percent Pd/C; In tetrahydrofuran; methanol; diphenylether; ethanol; dichloromethane; 3: Eschenmoser rearrangement / 5: Pauson-Khand reaction / 11: retro-Diels-Alder reaction / 12: Wolff-Kishner reaction;

DOI:10.1021/ol006922o

upstream raw materials:

(5S,6R,7R)-6,7,11,11-Tetramethyl-dispiro[3.0.4.2]undecan-6-ol

(+)-arnicenone

(–)-modhephene

(3aR,4R,7S,7aR)-2-Hydroxymethyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one

Refernces

• 1、 Saritas, Yücel,Von Reu, Stephan H.,K?nig, Wilfried A.. "Sesquiterpene constituents in Petasites hybridus". . p. 795 - 803. Retrieved 2002.
• 2、 Chatterjee,S.. "". . p. 620 - 621. Retrieved 1979.
• 3、 Iura,Sugahara,Ogasawara. "Enantio- and diastereocontrolled synthesis of an angular triquinane sesquiterpene (+)-arnicenone.". . p. 291 - 293. Retrieved 2007/10/03.