(S)-4,5-Dihydro-3-[(1Z,7Z)-hexadecan-7-enylidene]-4-hydroxy-5-methylenefuran-2(3H)-one

Base Information

• Chemical Name: (S)-4,5-Dihydro-3-[(1Z,7Z)-hexadecan-7-enylidene]-4-hydroxy-5-methylenefuran-2(3H)-one
• CAS No.: 58940-65-1
• Molecular Formula: C₂₁H₃₄O₃
• Molecular Weight: 334.499
• Mol file: 58940-65-1.mol

Synonyms:2(3H)-Furanone,3-(7-hexadecenylidene)dihydro-4-hydroxy-5-methylene-, [S-(Z,Z)]-;2(3H)-Furanone, 3-(7Z)-7-hexadecenylidenedihydro-4-hydroxy-5-methylene-,(3Z,4S)- (9CI); Obtusilactone B

Chemical Property of (S)-4,5-Dihydro-3-[(1Z,7Z)-hexadecan-7-enylidene]-4-hydroxy-5-methylenefuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4,5-Dihydro-3-[(1Z,7Z)-hexadecan-7-enylidene]-4-hydroxy-5-methylenefuran-2(3H)-one

There total 5 articles about (S)-4,5-Dihydro-3-[(1Z,7Z)-hexadecan-7-enylidene]-4-hydroxy-5-methylenefuran-2(3H)-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:

(2E,9Z)-2-((R)-1-Hydroxy-prop-2-ynyl)-octadeca-2,9-dienoic acid (144582-66-1) → isoobtusilactone B (58940-65-1,58940-66-2)

Guidance literature:

With silver carbonate; In benzene; at 80 ℃;

DOI:10.1246/cl.1992.1647

Reference yield:

isopropyl oleate (17364-07-7,22147-34-8,112-11-8) → isoobtusilactone B (58940-65-1,58940-66-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / LiN(i-Pr)C₆H₁₁ / tetrahydrofuran / -60 °C

2: 1.) BrMgN(i-Pr)2 / 1.) ether, 2.) ether, -40 deg C

3: NaHCO₃ / benzene / 1 h / 60 °C

4: aq.KOH / methanol; diethyl ether / Ambient temperature

5: Ag₂CO₃ / benzene / 80 °C

With potassium hydroxide; N,N-diisopropylamido-magnesium bromide; sodium hydrogencarbonate; lithium cyclohexylisopropylamide; silver carbonate; In tetrahydrofuran; methanol; diethyl ether; benzene;

DOI:10.1246/cl.1992.1647

Reference yield:

(2E,9Z)-2-((R)-1-Hydroxy-prop-2-ynyl)-octadeca-2,9-dienoic acid isopropyl ester (144582-65-0) → isoobtusilactone B (58940-65-1,58940-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq.KOH / methanol; diethyl ether / Ambient temperature

2: Ag₂CO₃ / benzene / 80 °C

With potassium hydroxide; silver carbonate; In methanol; diethyl ether; benzene;

DOI:10.1246/cl.1992.1647

upstream raw materials:

(2E,9Z)-2-((R)-1-Hydroxy-prop-2-ynyl)-octadeca-2,9-dienoic acid

isopropyl oleate

(2E,9Z)-2-((R)-1-Hydroxy-prop-2-ynyl)-octadeca-2,9-dienoic acid isopropyl ester