4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI)

Base Information

• Chemical Name: 4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI)
• CAS No.: 312728-63-5
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.21
• Mol file: 312728-63-5.mol

Synonyms:4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI)

Chemical Property of 4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI)

Chemical Property:

• Boiling Point: 194.6±9.0 °C(Predicted)
• PSA: 17.07000
• Density: 0.847±0.06 g/cm3(Predicted)
• LogP: 2.34380

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI)

There total 18 articles about 4,6-Heptadien-2-one, 3,5-dimethyl-, (3R,4E)- (9CI) 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:

(2RS,3S,4E)-3,5-dimethylhepta-4,6-dien-2-ol → (3S)-3,5-dimethylhepta-4,6-dien-2-one (312728-63-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

Reference yield:

(2RS,3S)-4-benzyloxy-3-methylbutan-2-ol → (3S)-3,5-dimethylhepta-4,6-dien-2-one (312728-63-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMAP; Et₃N / dimethylformamide / 10 h / 20 °C

2.1: H₂ / Pd-C / ethanol / 12 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -10 °C

4.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -70 °C

4.2: HMPA / hexane; tetrahydrofuran / 0.17 h

5.1: TBAF / tetrahydrofuran / 12 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

With dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrogenolysis / 3.1: Swern oxidation / 4.1: deprotonation / 4.2: olefination / 5.1: Elimination / 6.1: Dehydrogenation;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

Reference yield:

(2RS,3R)-4-benzyloxy-3-methylbutan-2-ol (312728-58-8) → (3R,4Z)-3,5-dimethylhepta-4,6-dien-2-one (312728-63-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / DMAP; Et₃N / dimethylformamide / 10 h / 20 °C

2.1: 90 percent / H₂ / Pd-C / ethanol / 12 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -10 °C

4.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -70 °C

4.2: HMPA / hexane; tetrahydrofuran / 0.17 h

5.1: 100 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

With dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrogenolysis / 3.1: Swern oxidation / 4.1: deprotonation / 4.2: olefination / 5.1: Elimination / 6.1: Dehydrogenation;

DOI:10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

upstream raw materials:

(2RS,3R,4E)-3,5-dimethylhepta-4,6-dien-2-ol

(2RS,3R)-4-benzyloxy-3-methylbutan-2-ol

(2R,3RS)-3-tert-butyldimethylsilyloxy-2-methylbutan-1-ol

(3E,5R,6RS)-6-tert-butyldimethylsilyloxy-3,5-dimethylhepta-1,3-diene

Downstream raw materials:

streptimidone

Refernces