(S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone

Base Information

• Chemical Name: (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone
• CAS No.: 869801-12-7
• Molecular Formula: C₂₈H₃₈O₃
• Molecular Weight: 422.608
• Mol file: 869801-12-7.mol

Synonyms:(S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone

Chemical Property of (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone

There total 23 articles about (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone 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:

(E)-2-Octenal (2548-87-0) + (4R)-4-{(2Z)-7-[(4-methoxybenzyl)oxy]hept-2-en-1-yl}cyclopent-2-en-1-one (676236-01-4) → (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone (869801-12-7)

Guidance literature:

(4R)-4-{(2Z)-7-[(4-methoxybenzyl)oxy]hept-2-en-1-yl}cyclopent-2-en-1-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(E)-2-Octenal; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

With methanesulfonyl chloride; triethylamine; In dichloromethane; at -20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02181

Reference yield:

(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate (115074-49-2) → (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone (869801-12-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

1.2: 93 percent / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 50 °C

2.1: 89 percent / KI / H₂O; various solvent(s) / 10 h / 130 °C

3.1: 89 percent / (i-Bu)2AlH / CH₂Cl₂; hexane / 0.75 h / -78 °C

4.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / 20 °C

4.2: 84 percent / tetrahydrofuran / -70 - 20 °C

5.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 20 °C

6.1: 93 percent / PCC / CH₂Cl₂ / 3 h / 20 °C

7.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

7.3: Et₃N / CH₂Cl₂

With potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; pyridinium chlorochromate; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; 4.2: Wittig reaction / 7.2: aldol reaction;

DOI:10.1016/j.tet.2006.01.051

Reference yield:

(Z)-9-((4-methoxybenzyl)oxy)non-4-enal → (S,E)-4-((Z)-7-((4-methoxybenzyl)oxy)hept-2-en-1-yl)-5-((E)-oct-2-en-1-ylidene)cyclopent-2-enone (869801-12-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium perchlorate; N-ethyl-N,N-diisopropylamine / dichloromethane; diethyl ether / 16 h / -78 °C / Inert atmosphere

2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 22 h / -78 °C / Inert atmosphere

3.1: triethylamine; 4-acetamidobenzenesulfonyl azide / acetonitrile / 10 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

5.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} / dichloromethane / 0.75 h / Inert atmosphere; Reflux

5.2: 16 h / 60 °C

6.1: sodium chloride / dimethyl sulfoxide / 0.92 h / 140 °C / Inert atmosphere

7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

7.2: 3 h / -78 °C / Inert atmosphere

7.3: 1.5 h / -20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; 4-acetamidobenzenesulfonyl azide; lithium perchlorate; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; sodium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 6.1: |Krapcho Dealkoxycarbonylation / 7.1: |Aldol Condensation / 7.2: |Aldol Condensation;

DOI:10.1021/acs.orglett.5b02181

upstream raw materials:

2-<(1R,4S)-4-hydroxycyclopent-2-enyl>malonsaeure-dimethylester

(1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene

(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate

methyl 2-((1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)acetate

Downstream raw materials:

15d-PGJ₂

(Z)-7-((R,E)-2-((E)-oct-2-en-1-ylidene)-3-oxocyclopentyl)hept-5-enoic acid