Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane
• CAS No.: 111613-41-3
• Molecular Formula: C15H24O
• Molecular Weight: 220.355
• DSSTox Substance ID: DTXSID601126980
• Nikkaji Number: J483.170E
• Mol file: 111613-41-3.mol

Synonyms:111613-41-3;112574-90-0;Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane;SCHEMBL9448689;DTXSID601126980;(1R,4S,6S)-4-[(1Z)-1,5-Dimethyl-1,4-hexadien-1-yl]-1-methyl-7-oxabicyclo[4.1.0]heptane;(1S,1'Z,2S,4R)-(?)-Epoxybisabolene;(1R,4S,6S)-1-Methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane

Chemical Property of Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane

Chemical Property:

• PSA: 12.53000
• LogP: 4.24660
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCC=C(C)C1CCC2(C(C1)O2)C)C
• Isomeric SMILES: CC(=CC/C=C(/C)\[C@H]1CC[C@@]2([C@H](C1)O2)C)C

Technology Process of Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane

There total 20 articles about Rel-(1R,4S,6S)-1-methyl-4-((Z)-6-methylhepta-2,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane 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: 58.0%

erythro-(1R,2S,4S)-4-(1',5'-Dimethyl-2'-diphenylphosphinoyl-1'-hydroxyhex-4'-enyl)-1,2-epoxy-1-methylcyclohexane (214333-53-6) → (Z)-(1R,2S,4S)-4-(1',5'-Dimethylhexa-1',4'-dienyl)-1,2-epoxy-1-methylcyclohexane (111613-41-3)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1055/s-2000-6253

Reference yield: 49.0%

6-Methyl-2-((1S,3S,6R)-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-3-phenylsulfanyl-hept-5-en-2-ol → (Z)-(1R,2S,4S)-4-(1',5'-Dimethylhexa-1',4'-dienyl)-1,2-epoxy-1-methylcyclohexane (111613-41-3)

Guidance literature:

With diphosphorus tetraiodide; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(97)10800-0

Reference yield: 49.0%

(2R*,3R*,1'S,3'S,4'R)-2-(3',4'-epoxy-4'-methylcyclohexyl)-6-methyl-3-phenylthio-5-hepten-2-ol (214333-57-0) → (Z)-(1R,2S,4S)-4-(1',5'-Dimethylhexa-1',4'-dienyl)-1,2-epoxy-1-methylcyclohexane (111613-41-3)

Guidance literature:

With diphosphorus tetraiodide; triethylamine; In dichloromethane; at -10 ℃; for 4h;

DOI:10.1016/S0040-4020(98)00696-6

upstream raw materials:

2-methyl-1-propenylbromide

(1R,4S,6S)-4-((Z)-3-Bromo-1-methyl-propenyl)-1-methyl-7-oxa-bicyclo[4.1.0]heptane

2-methyl-5-(phenylsulfonyl)-2-pentene

(1R,2S,4S)-4-Acetyl-1,2-epoxy-1-methylcyclohexane

Downstream raw materials:

(1R,2R,4S)-4-((Z)-1,5-Dimethyl-hexa-1,4-dienyl)-1-methyl-cyclohexane-1,2-diol

(2S,3S,6S,7Z)-3-acetoxy-2-methanesulfonyloxy-7,10-bisaboladiene

(2R,3R,6S,7Z)-2-acetoxy-3-methanesulfonyloxy-7,10-bisaboladiene