Elemol

Base Information

• Chemical Name: Elemol
• CAS No.: 639-99-6
• Deprecated CAS: 8024-27-9
• Molecular Formula: C15H26 O
• Molecular Weight: 222.371
• Hs Code.: 2906199090
• European Community (EC) Number: 211-360-5
• UNII: L92AJ7G06I
• DSSTox Substance ID: DTXSID1052323
• Nikkaji Number: J14.847D
• Wikidata: Q27282855
• Metabolomics Workbench ID: 110319
• ChEMBL ID: CHEMBL2287241
• Mol file: 639-99-6.mol

Synonyms:elemol;elemol, (1R-(1alpha,3beta,4beta))-isomer

Chemical Property of Elemol

Chemical Property:

• Melting Point: 46 °C
• Boiling Point: 152-156 °C(Press: 17 Torr)
• PKA: 15.18±0.29(Predicted)
• PSA: 20.23000
• Density: 0.9411 g/cm3
• LogP: 3.94200
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 290

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CC(CCC1(C)C=C)C(C)(C)O
• Isomeric SMILES: CC(=C)[C@@H]1C[C@@H](CC[C@@]1(C)C=C)C(C)(C)O

Technology Process of Elemol

There total 29 articles about Elemol 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: 72.0%

2-{(1R,3S,4S)-4-Methyl-3-[(S)-1-methyl-2-(2-nitro-phenylselanyl)-ethyl]-4-[2-(2-nitro-phenylselanyl)-ethyl]-cyclohexyl}-propan-2-ol (87059-28-7) → elemol (639-99-6)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; water; for 6h; Ambient temperature;

Reference yield:

(S)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one (83093-41-8,83093-45-2) → elemol (639-99-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 24 percent / potassium hydroxide, H₂ / 10percent palladium charcoal / ethanol / 0.5 h / 760 Torr / Ambient temperature

2: 91 percent / pyridine / 44 h / Ambient temperature

3: 97 percent / basic alumina

4: 94 percent / LAH / diethyl ether / 12 h / Heating

5: 92 percent / chromium trioxide / pyridine / 3 h / Ambient temperature

6: 99 percent / boron trifluoride etherate / benzene / 4 h / Ambient temperature

7: 76 percent / etheral methyllithium / tetrahydrofuran / 0.33 h / 0 °C

8: 77 percent / ozone, sodium borohydride / methanol; CH₂Cl₂ / 0.58 h / -77 °C

9: 84 percent / tri-n-butyl phosphine / tetrahydrofuran; pyridine / 18 h / Ambient temperature

10: 72 percent / NaHCO₃, NaIO₄ / methanol; tetrahydrofuran; H₂O / 6 h / Ambient temperature

With pyridine; chromium(VI) oxide; aluminum oxide; potassium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; tributylphosphine; boron trifluoride diethyl etherate; methyllithium; hydrogen; sodium hydrogencarbonate; ozone; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; benzene;

Reference yield:

Toluene-4-sulfonic acid 2-((2R,4aS,8aS)-4a,8-dimethyl-7-oxo-decahydro-naphthalen-2-yl)-2-hydroxy-propyl ester (87059-23-2,87059-30-1) → elemol (639-99-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / basic alumina

2: 94 percent / LAH / diethyl ether / 12 h / Heating

3: 92 percent / chromium trioxide / pyridine / 3 h / Ambient temperature

4: 99 percent / boron trifluoride etherate / benzene / 4 h / Ambient temperature

5: 76 percent / etheral methyllithium / tetrahydrofuran / 0.33 h / 0 °C

6: 77 percent / ozone, sodium borohydride / methanol; CH₂Cl₂ / 0.58 h / -77 °C

7: 84 percent / tri-n-butyl phosphine / tetrahydrofuran; pyridine / 18 h / Ambient temperature

8: 72 percent / NaHCO₃, NaIO₄ / methanol; tetrahydrofuran; H₂O / 6 h / Ambient temperature

With chromium(VI) oxide; aluminum oxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; tributylphosphine; boron trifluoride diethyl etherate; methyllithium; sodium hydrogencarbonate; ozone; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; benzene;

upstream raw materials:

2-[(1R,3S,4S)-4-(2-Iodo-ethyl)-3-((S)-2-iodo-1-methyl-ethyl)-4-methyl-cyclohexyl]-propan-2-ol

2-{(1R,3S,4S)-4-Methyl-3-[(S)-1-methyl-2-(2-nitro-phenylselanyl)-ethyl]-4-[2-(2-nitro-phenylselanyl)-ethyl]-cyclohexyl}-propan-2-ol

11-hydroxy-4α,5α-eudesm-3-one

trans-Dihydrocarisson-tosylhydrazon

Downstream raw materials:

(-)-O-(3.5-dinitro-benzoyl)elemol

(S)-6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1-methylethylidene)cyclohexene

δ-elemene

β-cyperone

Refernces

• 1、 Taber,Taber, Douglass F.,Wang. "Kinetic vs. thermodynamic control in intramolecular diene cyclozirconation: Synthesis of elemol". . p. 6639 - 6642. Retrieved 2007/10/02.
• 2、 Kutney, James P.,Singh, Ashok K.. "The chemistry of thujone. VII. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of β-elemol". . p. 1111 - 1114. Retrieved 2007/10/02.