7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-

Base Information

• Chemical Name: 7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-
• CAS No.: 36616-60-1
• Deprecated CAS: 117181-65-4,18383-50-1
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• European Community (EC) Number: 253-128-6
• UNII: S7C1X9QF3Q
• DSSTox Substance ID: DTXSID30884673
• Nikkaji Number: J1.028.092C
• Metabolomics Workbench ID: 28106
• Mol file: 36616-60-1.mol

Synonyms:36616-60-1;Carvone oxide;(R,R,R)-Carvone Epoxide;1-Carvone oxide;Carvone-5,6-oxide, trans-(+)-;UNII-S7C1X9QF3Q;NSC 316066;S7C1X9QF3Q;EINECS 253-128-6;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-;(+)-Carvone epoxide;p-Menth-8-en-2-one, 1,6-epoxy-, (1R,4R,6R)-(-)-;(1R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-one;(1r,4r,6r)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one;( )-Carvone epoxide;7-Oxabicyclo(4.1.0)heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-;NSC-316066;(R)-Carvoneoxide;7-OXABICYCLO(4.1.0)HEPTAN-2-ONE, 1-METHYL-4-(1-METHYLETHENYL)-, (1R-(1.ALPHA.,4.ALPHA.,6.ALPHA.))-;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, [1R-(1.alpha.,4.alpha.,6.alpha.)]-;(Z)-carvone-5,6-oxide;(+)-2,3-Epoxy-5-isopropenyl-2-methylcyclohexanone;SCHEMBL3364380;trans-(+)-carvone-5,6-oxide;DTXSID30884673;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, [1R-(1?,4?,6?)]-;(1R,4R,6R)-4-Isopropenyl-1-methyl-1,6-epoxycyclohexan-2-one;7-Oxabicyclo(4.1.0)heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R-(1alpha,4alpha,6alpha))-;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1.alpha.,4.alpha.,6.alpha.)-()-;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1.alpha.,4.alpha.,6.alpha.)-(+)-;L-(-)-CARVONE TRANS-EPOXIDE;LMPR0102090018;FEMA NO. 4084, TRANS-(+)-;C09841;Q27288773;(1r,4r,6r)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one;(1R,4R,6R)-1-METHYL-4-ISOPROPENYL-7-OXABICYCLO(4.1.0)HEPTAN-2-ONE;7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1?,4?,6?)-(++)-;117181-65-4

Chemical Property of 7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-

Chemical Property:

• Boiling Point: 255.6oC at 760 mmHg
• Flash Point: 107.6oC
• PSA: 29.60000
• Density: 1.086g/cm3
• LogP: 1.69910
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

(R,R,R)-CarvoneEpoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CC2C(O2)(C(=O)C1)C
• Isomeric SMILES: CC(=C)[C@@H]1C[C@@H]2[C@@](O2)(C(=O)C1)C
• General Description: (1alpha,4alpha,6alpha)-(+)-1-methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptan-2-one (1alpha,4alpha,6alpha)-(+)-1-methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptan-2-one, also known as 1-carvone oxide or carvone 1,2-oxide, is an epoxy derivative of carvone that serves as a versatile intermediate in organic synthesis. It has been utilized in Lewis-acid-mediated reactions with anisole derivatives to produce non-natural CBD analogues, demonstrating its utility in constructing complex scaffolds without requiring sensitive reagents. Additionally, its stereochemistry and reactivity make it a valuable precursor in enantiospecific syntheses of highly oxygenated terpenoids, as it can be derived from (R)- or (S)-carvone and further functionalized through reductive coupling and condensation strategies. These applications highlight its role in stereocontrolled synthesis and the preparation of bioactive molecules.

Technology Process of 7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)-

There total 10 articles about 7-Oxabicyclo[4.1.0]heptan-2-one, 1-methyl-4-(1-methylethenyl)-, (1R,4R,6R)- 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: 100.0%

(R)-Carvone (6485-40-1,2244-16-8) → (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol;

DOI:10.1055/s-2003-41025

Reference yield: 95.0%

Carvone (99-49-0,22327-39-5) → carvone epoxide (18383-49-8,33204-74-9,36616-60-1,39067-90-8,39903-97-4,39903-98-5,74608-55-2,117181-65-4)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; dodecyltrimethylammonium bromide; In n-heptane; water; at 25 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00270-7

Reference yield: 82.0%

Carvone (99-49-0,22327-39-5) → (1R,4R,6R)-4-Isopropenyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (18383-49-8,33204-74-9,36616-60-1,39067-90-8,39903-97-4,39903-98-5,74608-55-2,117181-65-4)

Guidance literature:

With tetrabutyl ammonium fluoride; dihydrogen peroxide; In tetrahydrofuran; dimethyl sulfoxide; at 17 ℃; for 6h;

DOI:10.1246/cl.1987.285

upstream raw materials:

5-Isopropenyl-2-methyl-cyclohex-2-enol

(-)-Carvone diepoxide

(R)-Carvone

Carvone

Downstream raw materials:

Carvone

dihydrocarveol

Hydroxycarvon