2,7-DIMETHYLOCTA-5(TRANS),7-DIENO-1,4-LACTONE

Base Information

• Chemical Name: 2,7-DIMETHYLOCTA-5(TRANS),7-DIENO-1,4-LACTONE
• CAS No.: 74183-60-1
• Molecular Formula: C10H14 O2
• Molecular Weight: 166.22
• Mol file: 74183-60-1.mol

Synonyms:2(3H)-Furanone,dihydro-3-methyl-5-(3-methyl-1,3-butadienyl)-, [3R-[3a,5a(E)]]-; 2(3H)-Furanone,dihydro-3-methyl-5-[(1E)-3-methyl-1,3-butadienyl]-, (3R,5R)- (9CI);(-)-Marmelolactone B; Marmelolactone B

Chemical Property of 2,7-DIMETHYLOCTA-5(TRANS),7-DIENO-1,4-LACTONE

Chemical Property:

• PSA: 26.30000
• LogP: 2.07030

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,7-DIMETHYLOCTA-5(TRANS),7-DIENO-1,4-LACTONE

There total 12 articles about 2,7-DIMETHYLOCTA-5(TRANS),7-DIENO-1,4-LACTONE 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: 83.0%

5-((E)-3-Hydroxy-3-methyl-but-1-enyl)-3-methyl-dihydro-furan-2-one (76638-28-3,76638-31-8,78304-87-7) → dl-marmelolactone (74133-35-0,74183-60-1,76704-00-2,76704-01-3,78548-56-8,88269-65-2,88269-66-3,88269-67-4,89016-29-5,125949-14-6,125949-15-7,139559-83-4,139559-84-5)

Guidance literature:

With methanesulfonyl chloride; triethylamine;

DOI:10.1016/S0040-4039(00)92830-2

Reference yield: 61.0%

(4R,5E)-7-Methyl-5,7-octadien-4-olide (88972-35-4) + methyl iodide (74-88-4) → (2R,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (74183-60-1) + (2S,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (89016-29-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -76 - -30 ℃; for 2h;

Reference yield: 53.0%

(2S,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (89016-29-5) → (2R,4R,5E)-2,7-Dimethyl-5,7-octadien-4-olide (74183-60-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -76 ℃; for 0.333333h;

upstream raw materials:

5-((E)-3-Hydroxy-3-methyl-but-1-enyl)-3-methyl-dihydro-furan-2-one

5-(2-Chloro-3-methyl-but-3-enyl)-3-methyl-dihydro-furan-2-one

2-(2-Methyl-allyl)-3-oxo-pentanedioic acid diethyl ester

3-Methyl-5-(3-methyl-but-2-enyl)-dihydro-furan-2-one

Downstream raw materials:

(2R,4R,5E)-2,7-Dimethyl-5,7-octadien-1,4-diol

marmelo oxide A

3,5-trans-marmelo oxide

3,5-cis-marmelo oxide

Refernces

• 1、 Nishida, Yoshihiro,Fukushima, Yuko,Ohrui, Hiroshii,Meguro, Heroshi. "The Enantioselective Synthesis of Marmelo Oxides A and B and the Assignment of the Absolute Configurations of Marmelo Oxides". . p. 1217 - 1222. Retrieved 2007/10/02.
• 2、 Torii, Sigeru,Uneyama, Kenji,Ono, Michio. "A NOVEL SYNTHESIS OF DL-MARMELOLACTONE AND DL-ROSE OXIDE BY ELECTROCHEMICAL OXYSELENENYLATION SEQUENCE". . p. 2653 - 2654. Retrieved 2007/10/02.