Cycloaraneosene

Base Information

• Chemical Name: Cycloaraneosene
• CAS No.: 110990-41-5
• Molecular Formula: C20H32
• Molecular Weight: 272.474
• DSSTox Substance ID: DTXSID401102661
• Nikkaji Number: J328.394A
• Wikidata: Q74411696
• Mol file: 110990-41-5.mol

Synonyms:Cycloaraneosene;110990-41-5;CHEBI:138247;DTXSID401102661;C21726;(1R,3aR,9aS,10aR)-1,2,3,3a,4,5,6,8,9,9a,10,10a-Dodecahydro-1,9a-dimethyl-4-methylene-7-(1-methylethyl)dicyclopenta[a,d]cyclooctene;(1R,3aR,9aS,10aR)-1,9a-Dimethyl-4-methylene-7-(propan-2-yl)-1,2,3,3a,4,5,6,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene;(1R,3aR,9aS,10aR)-7-isopropyl-1,9a-dimethyl-4-methylene-1,2,3,3a,4,5,6,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d]cyclooctene;(1R,3S,11R,14R)-3,14-dimethyl-10-methylidene-6-propan-2-yltricyclo[9.3.0.03,7]tetradec-6-ene;(6aR)-3-Isopropyl-1,2,4,5,6,6abeta,7,8,9,9aalpha,10,10a-dodecahydro-6-methylene-9beta,10abeta-dimethyldicyclopent

Chemical Property of Cycloaraneosene

Chemical Property:

• PSA: 0.00000
• LogP: 6.14150
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 272.250401021
• Heavy Atom Count: 20
• Complexity: 439

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C1CC3(CCC(=C3CCC2=C)C(C)C)C
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@@H]1C[C@@]3(CCC(=C3CCC2=C)C(C)C)C
• 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 (-)-cycloaraneosene, is a tricyclic diterpene hydrocarbon with a 5-8-5 ring system, serving as a fundamental scaffold for "epi"-fusicoccane diterpenoids. Its structure features a fused dicyclopenta[a,d]cyclooctene core with an isopropyl group at C-3, a methylene group at C-6, and methyl groups at C-9β and C-10aβ. The stereochemistry was confirmed through total synthesis involving iridoid dimerization, Cope rearrangement, and reduction. Notably, its hydroxylated congener was revised from the initially proposed 9α-hydroxy to an 8β-hydroxy configuration based on synthetic and spectroscopic comparisons. **Returned paragraph:** (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) is a tricyclic diterpene hydrocarbon with a 5-8-5 ring framework, key to the "epi"-fusicoccane family. It contains an isopropyl group, a methylene bridge, and two methyl groups in specific stereochemical orientations, confirmed by total synthesis. Structural revisions of its hydroxylated derivative clarified the natural product as the 8β-hydroxy isomer. (No null return, as the abstracts provided relevant structural and synthetic context.)

Technology Process of Cycloaraneosene

There total 32 articles about Cycloaraneosene 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: 95.0%

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 (110990-43-7) → (-)-cycloaraneosene (110990-41-5)

Guidance literature:

With lithium; In tetrahydrofuran; ammonia; tert-butyl alcohol; at -78 ℃; for 0.5h;

DOI:10.1246/bcsj.61.3231

Reference yield:

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 (110990-51-7) → (-)-cycloaraneosene (110990-41-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / H₂ / PtO₂ / acetic acid / 24 h / 15 - 25 °C

2: 40 percent / LAH / tetrahydrofuran

3: 1.) (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 15 min.; 2.) CH₂Cl₂, DMSO, THF, 30 min.

4: 86 percent / Et₃N / CH₂Cl₂ / 15 h

5: 75 percent / Pd(OAc)2 / acetonitrile / 6 h / 15 - 25 °C

6: 72 percent / 1.8 M DIBAH / toluene; hexane / 0.5 h / -78 °C

7: 1.) rose bengal, pyridine; 2.) PPh₃ / 1.) 0-5 deg C, 20 min., irr., acetone; 2.) acetone, 15-25 deg C, 15 h

8: 76 percent / pyridine / toluene / 15 h / 0 °C

9: 78 percent / CrCl₂ / tetrahydrofuran; dimethylformamide / 15 h / 0 °C

10: 96 percent / pyridine / 15 - 25 °C

11: 95 percent / Li / liquid ammonia; tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / -78 °C

With pyridine; chromium dichloride; palladium diacetate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; lithium; rose bengal; diisobutylaluminium hydride; triethylamine; triphenylphosphine; platinum(IV) oxide; In tetrahydrofuran; pyridine; hexane; dichloromethane; ammonia; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1246/bcsj.61.3231

Reference yield:

(5S)-isopropyl-2-methylcyclopent-1-enecarboxaldehyde (62994-35-8) → (-)-cycloaraneosene (110990-41-5)

Guidance literature:

Multi-step reaction with 19 steps

1: CrCl₂

3: Heating

4: KF / tetrahydrofuran / 48 h / 15 - 25 °C

5: Florisil, KF / methanol / 24 h / 15 - 25 °C

6: 96 percent / LAH / tetrahydrofuran / 2 h / 15 - 25 °C

7: 95 percent / pyridinium p-toluenesulfonate

8: 97 percent / H₂ / 5 percent Pd/carbon / ethanol / 23 h / 15 - 25 °C

9: 95 percent / HMPA, Na / 2-methyl-propan-2-ol / 15 h / 15 - 25 °C

10: 70 percent / p-TsOH / methanol / 3 h / Heating

11: 1.) (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 15 min.; 2.) CH₂Cl₂, DMSO, THF, 30 min.

12: 86 percent / Et₃N / CH₂Cl₂ / 15 h

13: 75 percent / Pd(OAc)2 / acetonitrile / 6 h / 15 - 25 °C

14: 72 percent / 1.8 M DIBAH / toluene; hexane / 0.5 h / -78 °C

15: 1.) rose bengal, pyridine; 2.) PPh₃ / 1.) 0-5 deg C, 20 min., irr., acetone; 2.) acetone, 15-25 deg C, 15 h

16: 76 percent / pyridine / toluene / 15 h / 0 °C

17: 78 percent / CrCl₂ / tetrahydrofuran; dimethylformamide / 15 h / 0 °C

18: 96 percent / pyridine / 15 - 25 °C

19: 95 percent / Li / liquid ammonia; tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / -78 °C

With pyridine; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; potassium fluoride; florisil; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium; pyridinium p-toluenesulfonate; lithium; rose bengal; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; ammonia; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1246/bcsj.61.3231

upstream raw materials:

(1R,3aR,9aS,10aR)-7-Isopropyl-1,9a-dimethyl-1,2,3,3a,4,5,6,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cyclooctene-4-carbaldehyde

((1R,3aR,9aS,10aR)-7-Isopropyl-1,9a-dimethyl-1,2,3,3a,4,5,6,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-4-yl)-methanol

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

9α-hydroxycycloaraneosene