(1R,6E,10R)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one

Base Information

• Chemical Name: (1R,6E,10R)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one
• CAS No.: 32179-17-2
• Molecular Formula: C15H22O2
• Molecular Weight: 234.33400
• DSSTox Substance ID: DTXSID101345701
• Mol file: 32179-17-2.mol

Synonyms:DTXSID101345701

Chemical Property of (1R,6E,10R)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one

Chemical Property:

• Boiling Point: 340.8±41.0 °C(Predicted)
• PSA: 29.60000
• Density: 1.011±0.06 g/cm3(Predicted)
• LogP: 3.56970
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 399

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC2(C(O2)CC(=C(C)C)C(=O)C1)C
• Isomeric SMILES: C/C/1=C\CC[C@@]2([C@H](O2)CC(=C(C)C)C(=O)C1)C

Technology Process of (1R,6E,10R)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one

There total 13 articles about (1R,6E,10R)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one 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: 79.0%

germacrone (6902-91-6) → germacrone-1,10-epoxide + (4S,5S)-(+)-germacrone 4,5-epoxide (32179-17-2,70680-71-6,92691-35-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 6h; Inert atmosphere;

DOI:10.1002/chem.201300662

Reference yield: 19.0%

germacrone (6902-91-6) → 1,10-epoxygermacrone (52061-45-7,106862-05-9,142794-64-7) + (+/-)-germacrone-4,5-epoxide (32179-17-2,70680-71-6,92691-35-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

DOI:10.3390/molecules24162898

Reference yield: 2.0%

(4S,5S)-epoxy-(+)-4,5-dihydrogermacrone (32179-17-2,70680-71-6,92691-35-5) → (+/-)-Germacron-5,6-epoxid (32179-17-2,70680-71-6,92691-35-5) + (1S,10S),(4S,5S)-germacrone-1(10),4-diepoxide (32179-18-3,70629-66-2,70629-67-3,120787-82-8,133098-06-3,135682-22-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Ambient temperature;

upstream raw materials:

germacrone

(4S,5S)-epoxy-(+)-4,5-dihydrogermacrone

Downstream raw materials:

curcumenone

procurcumenol

dihydrocurcumenone

C₁₅H₂₀O

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